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Estonia’s George Smiley retires: The life and times of a counterintelligence “legend”

Aleksander Toots, the Deputy Director General of the Estonian Internal Security Service (KAPO) and the long-time head of Estonian counterintelligence, resigned at the end of March. The tight-lipped Toots, known among his allies and enemies alike as one of the most effective interrogators in the world, rarely speaks to the press. But he made an exception for Estonian journalist Eero Epner. The Insider has received permission to print Epner's story of how Toots became a “breaker of human souls” — a figure feared both by Estonia's enemies, and by his own colleagues.

This article was translated from Estonian. It originally ran in the Estonian news magazine Delfi.

Aleksander Toots is not easy to understand. He smiles a lot, but rarely jokes. According to Toots himself, there are only a few in the Estonian Internal Security Service (KAPO) who get his humor.

Throughout his career, Toots has refused almost all interview requests, but when he finally starts talking, he can go on for hours. He remembers sentences that he — or you — said years ago, and yet sometimes he has trouble getting a cup of cappuccino to trickle out of the coffee machine. At the beginning of one of our conversations, Toots slowly and methodically cleans his glasses for close to ten minutes. Later, he calmly circles his index finger around the bottom of his coffee cup while emphasizing that emotions must never get the best of one. Despite the expressed sentiment, Toots often ends his messages with smiley faces.

“Aleksander is a cross between John le Carré’s George Smiley and an Eastern Bloc gymnastics coach from the 1980s,” says Michael Weiss, an editor at The Insider and a journalist who has written tomes worth of stories about intelligence. “He is a thorough researcher with a very rare level of discipline, and his personality is absolutely impenetrable.”

The nature of his work requires the ability to think like a chess master without looking too bookish, and so for meetings, he usually wears brand name shirts — Tommy Hilfiger and the like — with short sleeves that show off his rough and ready arms. Toots talks about how counterintelligence requires incessant adjustment, the constant changing of tactics and approaches in order to continue keeping the adversary on his toes. “It's creative work,” says Estonia’s best in the business.

In his free time, Toots runs all variety of long distance races. In some, he trudges along for twenty-four hours straight, covering more than a hundred kilometers. In others, Toots has been seen running along sea water, or over slippery beach stones, or on snow in minus ten degrees. It requires a tolerance for repetitive routine and an almost superhuman resistance to numbness, but above all, the ordeals require a relentless pursuit of one’s goal. “He's like a hunting dog who can't be thrown off the scent,” says Kaimo Kuusk, the long-time Deputy Director General of the Foreign Intelligence Service. “Once he’s on the trail, he won't stop until he tracks down his prey.”

Toots says he still feels fresh and hungry. Not too far away in Moscow, the Russian spy machine is still a colossus — one that has been even more aggressive than usual in recent years. This competition helped keep Toots, who has outlasted most of his contemporaries in the Estonian service, in shape. According to the recently retired chief, “very, very, very few” of those who were there at the beginning of the counterintelligence division’s founding still roam its corridors.

When Inna Ombler was still a prosecutor, she and Toots often crossed paths in the corridors of the KAPO Office, where they would sit down and start chatting about — among other things — the history of Russia, which both of them know in such detail that the talks soon turned into a kind of competition. When Russia exhausted itself as a topic of conversation, Toots would turn to genealogy, tracing his roots back for generations to the refined Baltic German gentlemen whose distant blood still flows through the veins of the counterspy born in the sooty mining settlements of Ida-Virumaa, an Estonian county on the Gulf of Finland that was heavily Russified during the Soviet occupation that followed World War II.

Sometimes, upon request, Toots even compiles family trees for his friends. When I ask Toots who knows him best, I expect to hear the name of a colleague, or at least a friend, but he replies instead with his trademark feline half-smile, “My parents.” Both are still alive, but he does not grant me a meeting and says almost nothing about them himself. If questions touch too closely to his own psychology, one can sense a not-so-hidden irritation emanating from the other side of the table. “We don't profile me,” Toots says abruptly.

Counterspies, of course, are adept at counter-profiling — talking ad nauseam while in reality creating a completely false impression for their interlocutors. Why, then, is Toots so ready to talk to me when, at the same time, the organization he heads takes such pains to control its employees’ public profile? Would Toots have allowed any of his subordinates to do such a thing? Or, does he want to talk more broadly about the end of a process that is not necessarily related only to him, but to a broader stage in Estonian security? Why is he willing to let me, who knows little enough about the security world, be his interviewer? Is it because he expects I will sit in awe? Is it because he knows I will not know enough to know which sensitive questions to ask? Am I not also one of the chess pieces in the Toots games? What form of prey is he, as always, relentlessly pursuing via his conversation with me? I do not know. Aleksander Toots is careful, cunning, and insightful enough not to give any hint of the potential next moves he is calculating in his head.

However, when Toots does begin to put himself on the couch, the figure he describes is essentially a psychologist. His main job for the last few decades has been to penetrate the souls of traitors and spies, then break them down to the point that they confess, giving up the game. In some particularly masterful cases, the broken grows so attached to the breaker that he is happy to see him coming back towards the cell for the next session.

Toots' main job for the last few decades has been to penetrate the souls of traitors and spies, then break them down to the point that they confess, giving up the game.

“Our game with human souls is not the most ethical activity, but there are no other options,” says Toots during one of our meetings. “And we only console ourselves with the fact that we do everything for a holy cause.” Then he is silent for a moment and asks with a slight smile: “Good excuse, isn't it?” I admit, I'm getting a little queasy at this point.

Toots has many tactics useful in breaking an opponent, but he is not willing to talk about them in detail, only mentioning that the process starts immediately after the suspect is detained. I remember the video in which Toots spoke to traitor Herman Simm and his wife in a soft voice, as if helping an old man across the street. Maybe he knew how attached Simm was to his lady, but maybe he also knew how arrogant Simm himself was — you have to talk to people like that with respect, as if they were a party boss.

The men got into the car. Simm was silent as Toots spoke for ten minutes. “After that, he was ready to cooperate,” Toots later tells the host of the TV show that made the recording.

Convicted Russian spy Hermann Simm was released on probation from Tartu Prison on December 23, 2019
Convicted Russian spy Hermann Simm was released on probation from Tartu Prison on December 23, 2019
Photo: Terje Lepp

In the case of Aleksei Dressen, things were different. There the force was applied quickly and aggressively. Dressen's hands were twisted behind his back, and he was restrained on both sides as Toots walked up to him and presented the accusation in a low, formal voice. By this point, the two men had been colleagues for years, even decades — they had exchanged ideas in the coffee corner. Now Dressen was suddenly a stranger to him. Toots addressed the new stranger in a formal manner, the way one speaks to an unfamiliar bureaucrat rather than the way one speaks to a long-time comrade-in-arms. The traitor could not rely on any old emotional ties to save him.

“What could Toots have felt?” Toomas Sildam, who met Toots as a journalist in the 90s, asks me. I can't answer him. I ask Toots himself about this several times, but he persistently repeats: nothing. “I turned off my emotions,” he says. “I was a hound.”

Toots describes himself as a “difficult leader” and an “unpleasant fruit” who is blunt and rarely — if ever — offers praise.

And Toots can be much tougher still with his colleagues and partners. Working in a security agency is extremely stressful in itself, but Toots has pushed his team to work for his goals so mercilessly — for years — that not all of them can endure. “I have been unfair, and I remember those moments,” admits Toots. He describes himself as a “difficult leader” and an “unpleasant fruit” who is blunt and rarely — if ever — offers praise. When I ask the new Director General of KAPO, Margo Palloson, how he managed to hold up under Toots, he curtly replies: “I found a way.”

There are some people who, when they hear the name Toots, immediately refuse to comment. They admit that Toots is in the top ranks of the world’s counterintelligence profession — “legend” is the word I hear from them most frequently — but as a human being, they have so much resentment or trauma that they turn their backs at the sound of his name. “I am who I am,” says Toots calmly. “I'm not interested in creating a false image.”

Many admit that Toots is in the top ranks of the world’s counterintelligence profession — “legend” is the word I hear from them most frequently.

Toots has been talking to one of KAPO’s office workers — a woman — every day for almost ten years. “I know that he creates mixed feelings in people,” she tells me. “But he has a tender soul inside.” She is one of the few whom Toots appears to trust, and even she doesn't know exactly why. With everyone else, it’s as if Toots has some kind of curtain in front of him. He goes to the coffee corner, but there he watches, brags, says borderline unbelievable things, tests people. “He's doing it for fun,” surmises one of his colleagues. “He just has this habit, he wants to track people,” says another. This colleague sometimes feels like Toots throws him overboard when he's not needed — and keeps him close when he is. But when we leave the concrete basement of the new main building of the KAPO office, this subordinate says quietly: “I do believe that he has a really kind soul inside, but why is he hiding it so fiercely?” The KAPO employee’s point? When a person takes such pains to hide something, it is because this something really does exist.

When talking about his work, Toots emphasizes rationality, argumentation, logic, systematicity and, above all, life experience, which is the greatest asset in the toolbox of a counterintelligence officer. According to his colleagues, the phrase “Sass [short for “Aleksander”] is playing his games again” is commonly heard among KAPO employees. Toots repeatedly refers to his more than 30-year career in the service, where he has become probably one of the most important counterintelligence specialists in Europe, as “decades in the amateur theater.” Although he reveals his cat-like, slightly suppressed smile again, you can sense the well-hidden exhaustion underneath. I tell him about lawyers who have taken to drinking because they so often have to assume a new face, a new role with each client. Toots seems to understand the comparison all too well. However, instead of drinking, Toots tills the earth around his country house, or else takes out a tracksuit and runs for up to a full day at the stadium if that’s what needs to be done to stay grounded.

Security agencies work under great pressure and play for high stakes, says Arnold Sinisalu, the former Director General of the KAPO, on a sunny Saturday spring morning in the lobby of a hotel in Tartu. Sinisalu moved to Tartu after decades spent living apart from his family — because of work, of course. Some former practitioners from the field may try to make up for lost time by letting go of old professional habits, but I notice how Sinisalu looks over his shoulder and scans each additional newcomer to the lobby.

Arnold Sinisalu, KAPO Director General from 2013 to 2023
Arnold Sinisalu, KAPO Director General from 2013 to 2023
Photo: Madis Veltman / Postimees

“I can sense the difference between generations,” says Sinisalu with a slightly sleepy face, even though it is already past noon. He and Toots both started at KAPO in the early 1990s, and it does not sound trite when Sinisalu says that an independent country was the fulfillment of his former colleague’s childhood dream. “The Republic of Estonia is of great value for me,” says Toots of his homeland, which in 1991 jumped at the opportunity to escape from Moscow’s grasp. “Our ancestors have worked hard for this. Everything I've done, I've done for the sake of the survival of this country.”

Regularly working more than 14 hours a day, sacrificing weekends, and leaving family life behind were not uncommon sacrifices for those in the service. While working in Ida-Virumaa, Sinisalu and Toots drove to meetings in an old blue Mazda with plexiglass paneling, but no one asked for comfort. “We were young and enthusiastic, we really wanted to contribute to the creation of the Republic of Estonia,” says Toots. “The Russian troops were inside, but we didn't feel fear.”

Among today’s younger generation, some think that the republic is a fact of life, that there is no value in comparing the present to the past. “They take as natural what we don't take as natural,” says Sinisalu, who still talks about KAPO in the possessive form even though he left it almost a year ago. The younger generation wants to live a life of variety, and staying in one institution for decades is no longer desirable. According to Sinisalu, this is fine. His generation would go to work every morning for the sake of normality, but it is natural that new normalities emerge. After all, Estonians’ freedom to develop along a path of their own choosing is exactly what the “old” normality was endeavoring to secure.

Aleksander Toots does not hide the fact that he is still in good shape. He has run his best marathon times recently, at several years over 50, and mentally, he says he is not one iota worse than he was in the early 1990s. “You have to live in such a way that the best is not yet over,” he says. A few years ago, he considered leaving the service for personal reasons, but then he stayed. When Arnold Sinisalu said that he would leave the position of Director General of the KAPO within a couple of years and that it would be good to start looking for a reliable successor, the position was offered to Toots. He had already met with the Chancellor about retiring, but gave up. “I'm not commenting,” says Toots about the period. Then he adds something I hear so much in our conversations: “I have a selective memory.” He smiles every time he says this.

“You have to live in such a way that the best is not yet over,” Toots says.

When Margo Palloson, a former counterintelligence officer under Toots, was chosen as the new Director General, Sinisalu asked Toots to stay for at least another year. Palloson rose to the top from the position of office manager. He had not been a deputy director and needed someone to help him get familiar with various issues. Sinisalu himself left. Second Deputy Director Martin Arpo resigned from office. In recent years, a whole generation had left or was about to leave the KAPO, as well as other security agencies — and the army. Toots promised to stay a little longer, knowing that soon enough he really would follow his former colleagues out the door. Too many “personal things” had been neglected. The stress was continuing to take its toll. And to be head of counterintelligence for 16 years is no small task. Yes, the Russian special services had become even more brazen, of late, but Toots felt sure his troupe could continue this show — even without its ringleader. He discussed it with the family, because “the family is alpha and omega,” and made the decision to retire.

When I ask sometime in the early winter if he's going to change his mind, Toots says he's a Sagittarius, and those born under such a star burn with flame — Sagittarians don't change their minds so easily. His farewell party will be held on International Theater Day, 27 March. “I wonder how you all could put up with me for 16 years,” says the good-natured Toots, whom everyone I talk to calls Sass. They say that he has a romantic and tender side, but can also be a real brat. Our counterspy, who together with his team has captured and prosecuted more than 20 Russian and Chinese officers along with several domestic traitors, will be awarded as parting gifts: a Haruki Murakami book about running, a shirt from the Estonian brand “will to defend,” and a cactus. There are those who wanted to give him a pack of “cow” candies — a kind of Soviet-legacy caramel — but there are different kinds of “cows,” and no one knows exactly which kind Toots likes, and you can't take chances with things like that. Then Margo Palloson makes a speech and gives his former boss, Sass, the Order of Merit of the KAPO Service, Class I. This is the highest award that can be given by the Director General. To date, fewer than ten people have received it.

Toots, who with his colleagues captured and prosecuted more than 20 Russian and Chinese officers, along with several domestic traitors, will be awarded as parting gifts: a Haruki Murakami book about running, a shirt from the Estonian brand “will to defend,” and a cactus.

The next day — Aleksander Toots’ last at work — when I sit down with him for the final time in the concrete basement and ask him if he is sad. Toots spreads his arms, smiles widely, and asks: “Is this what a person who is sad looks like?” In the evening, he is not going to have a quiet moment at dusk. Instead, a hard training session up the hill is planned, because the running season is about to start in Ida-Virumaa. Toots thinks for a moment when I ask him what he’s most satisfied with from his 30 years in the police force. “With the fact that I remained myself,” says the long-time member of the real life theater troupe.


Right from the start, Aleksander Toots was exactly what a true spy should be: inconspicuous. His classmates admit that they have no special memories of him. He showed up to school every day, always very politely dressed and with his hair combed.

In school he was quiet. It is remembered that he sometimes went for a walk with the dog. He participated in the activities of the boys’ club, went hiking with the other members. One trip led far into the Karakum desert. They spent the night in tents, felt the warm breath of the sand. Riho Altnurme, a professor of religious history who graduated from school one year earlier than Toots, thinks he remembers that the future counterintelligence ace read books and watched movies, and probably went shooting at the range in Kohtla-Järve, an industrial city where ethnic Russians make up the majority. He got along well with everyone, but didn't stand out. “Modest, matter-of-fact, and serious,” says Altnurme, who refuses to forward a photo of the two of them in a social situation — a snapshot that might have appeared to contradict the verbal description Toots’ former classmate had just put on the record. Altnurme does not consider his former classmate’s career path to have been a surprise. “His sense of justice was such that it was suitable for law enforcement,” he says. “You could be sure of him. He did not hesitate or doubt.”

“He was more of a quiet observer,” says classmate Terje Rattur. To this day, Toots eagerly attends class reunions, but afterwards, everyone admits that Toots yet again did not say anything about himself. Instead, he observed others, studied this and that, and questioned.

Even as a child, Toots melted into his surroundings like a spring flower. As theater actor and director Üllar Saaremäe is preparing for our interview, he accidentally finds a decades-old photo from student camp and, only when examining it, discovers that Toots was also there. Saaremäe did not remember his presence.

When Toots was about 13 years old, someone took a wallet from the school librarian's coat pocket, something not too uncommon back then in this neck of the woods. The militia showed up, they started to investigate the matter, and for some reason, they also asked the opinions of the students. Toots assumed that the thief must have been from outside the school. “I used the process of elimination,” he smiles. If the thief had been from school, why did he make his move only now? No, it had to be someone from the village. Some time passed, and the thief was caught. The math teacher looked at Toots and said he could be a detective.

However, no fables about predestination should be constructed. Toots shakes his head when I ask why he became a soul breaker. He doesn't even know exactly. Everything was bright enough in his childhood. Yes, his grandfather was recognized as a kulak — one of the “rich peasants” dispossessed by Soviet authorities. Everything was taken away, Toots’ grandfather was sent off to Siberia, and Toots’ father had to hide in a hayloft with his mother. But that family history couldn’t have been what drove Toots to torment the souls of those who still cooperate with Estonia’s enemies. He only recently heard about the hayloft. Silence seems to run in the family.


Kohtla-Nõmme was a peaceful and quiet pine town at that time. Folk dances were performed in the club, sports were played, and hiking trails snaked around the settlement. It was idyllic. The mine provided work, but the management there spoke Estonian. Kohtla-Nõmme was generally the only mining settlement in Ida-Virumaa where there were more Estonians than Russians. “Russian was not heard on the streets,” claims Altnurme. Immigrants had married, learned the local language, and become Estonian. “I don't remember any conflict between Russians and Estonians,” confirms Altnurme.

Toots’ memories are different. “In Kohtla-Nõmme, the Russians always got it,” he says, and “it” was not a good thing. In his telling, the situation was so serious that at one point the Russians of Kohtla-Järve did not even dare to show themselves. Toots grew up a few kilometers away from the center of Kohtla-Nõmme, in Kohtla station, among railway workers. There were many more Russians here, and by playing, talking, and fighting with them in the streets, Toots also learned the Russian language. Right down to the nuances.

According to Toots, the intricacies of the Russian language are so rich that sometimes the outcome of whole negotiations — or the breaking of people — can all depend on choosing the right word.

It has become one of Toots’ most important tools. “He knows the Russians inside and out,” says Margo Palloson. “And his Russian is perfect.” According to Toots, the intricacies of the language are so rich that sometimes the outcome of whole negotiations — or the breaking of people — can all depend on choosing the right word. Toots learned the language not of Dostoyevsky, but of the streets, and today's Russia is run by the kinds of former street thugs Toots grew up scrapping with. He repeatedly gives examples of how it is possible to draw far-reaching conclusions about the mindset of Vladimir Putin and his lackeys based on the phrasings that they use. Toots knows the Russians inside and out. Knows how they think. What they want. And he uses that knowledge against them.

Toots learned the language not of Dostoyevsky, but of the streets, and today's Russia is run by the kinds of former street thugs Toots grew up scrapping with.

Unlike Altnurme, Toots remembers fighting with the Russians himself — on countless occasions. Stone battles took place at Kohtla station. Toots hit and was hit. But he doesn't think he holds any particular grudge against the Russians over the whole thing. “I have no complexes about nationalities,” he says, claiming that he still has several Russian friends from childhood. About a decade ago, he told a local reporter that he still considers himself an Easterner, and some years back Toots bought a summer home near his old childhood haunts. His former colleague Sinisalu calls the place “very okay” and says Toots slips off to it whenever possible (even if Toots himself refuses to give its exact location). Although Ida-Virumaa's running events are not the biggest — around one hundred participants typically gather — Toots is almost always there. “The company is pleasant and friendly,” he told Erik Gamzejev, the editor-in-chief of Põhjarantnik, a newspaper published in the largely Russian-speaking Ida-Viru county, where Toots grew up.

When Margo Palloson served for a short time with Toots in Ida-Virumaa, he was treated to more local lore than he probably cared to know. Toots would deliver lengthy impromptu lectures about where one or another battle of the Second World War took place, or of what special feature this or that area around town boasted. Toots has never been a Tallinner.


After finishing elementary school, most of the graduates of Kohtla-Nõmme elementary school went on to high school. But not Toots. His maths especially tended to be bad. Logical conclusions didn’t seem to be his forte. But when he pulled himself together, he got things done there too. In 1986, when Toots had to choose where to continue his studies, he decided on the maritime school.

There are many sailors in Toots’ family — even his father had worked as a sailor before his son was born and he transitioned to life underground in the mines. Looking at him now, one might assume that Aleksander Toots would have wanted to become captain — or at least a coxswain — but instead he went to learn the ideal maritime trade for a cold fish: refrigeration mechanic.

At that time, it was mostly Estonians studying in Tallinn’s first vocational secondary school, and there were many pro-independence lecturers. When Toots entered the maritime school, it was already the end of the 1980s, and at one point he joined ERSP, a political party with the bold and radical aim of breaking away from the Soviet Union. “During this period in Ida-Virumaa, showing favoritism and doing something for Estonia definitely required firmness of principle and uncompromisingness,” says Toots’ childhood friend Veiko Taluste. “Back then, no one knew what would happen next.”

Toots didn’t stay put, but traveled around Ida-Virumaa. Once a week, he went to the rectory in Jõhvi with a group of about ten people to discuss political matters. At one of the gatherings, the idea came up to take down the local statue of Lenin. At that moment, Lenin had only been removed in Tartu, and repeating the feat here in Ida-Virumaa seemed almost unthinkable. And yet, hardly a few days later, Toots again drove to Jõhvi with some friends. An adult brought in a crane, a gantry was made, and a member of the revolutionary group climbed up and put a noose around the revolutionary monument’s neck.

A militia patrol passed by, seeing everything and doing nothing to stop it. The crane jerked, and it turned out that Lenin had not taken root. He toppled right away. The statue was placed in the back of a truck and taken away. Not even Aleksander Toots knows where the hunk of metal finally disappeared to. All in all, the process took a little over a quarter of an hour. “It made a big splash in Ida-Virumaa,” says Taluste.

Toots remembers the events of that time well. He also remembers how in the good old days of 1988 they put a blue-black-white Estonian tricolor on the end of a fishing rod — a sign of independence. This time, the militia took more of an interest, and Toots was taken to the station. He knew this offense would mean expulsion from the maritime school, and so the future KAPO man ran from the cops. They couldn't catch him.

During one of our meetings in the basement of the KAPO, Toots suddenly takes out an Estonian Soviet Socialist Republic flag from his bag and unfolds it. This is his trophy. When Soviet hardliners’ doomed putsch began in August 1991, Toots was driving from Ida-Virumaa to Tallinn. He hadn't heard the news, and he didn't know anything about the events in Moscow, but he saw that someone had raised this flag. He stopped the car, got out, dragged himself up the pole, tore the banner down, and kept it as spoils of war. Aleksander Toots had developed into a convinced nationalist — one willing to do what needed to be done, regardless of the risk.


At the maritime school, Toots came to understand that a life at sea was not for him. He told his class’s teacher that he would like to go to militia school. “I had read too many books,” Toots says. The class teacher talked him out of it and advised him to join the army first.

In 1989, Toots was drafted and sent to serve on the territory of the Ukrainian Soviet Socialist Republic. There he stayed for the next few years, quickly rising to the rank of master sergeant. When I ask Toots how much being in the military helped him later on, he quickly says, “A lot.”

When I ask Toots how much being in the military helped him later on, he quickly says, “A lot.”

There is a story from this time that Toots has told to his younger colleagues. The Soviet soldiers were given two days to build some kind of asphalt site in the missile force section. They had no gravel, no asphalt, no machinery. There was also no vodka with which such supplies could have been obtained from the local population. And yet, the site was still ready in the appointed time, with the use of supplies having been procured from God knows where. “You have to be creative,” is all Toots will say about how they got the job done.

Toots knew well what was going on at home, and he and a few other Estonians had opportunities to desert during the holidays. But Toots didn't do it. He felt he owed a debt of gratitude to the Russian officer who let them go on vacation. “He was human,” says Toots without elaborating. If Toots had run away, “I wouldn't have kept my word,” he says. Why hurt someone who has taken a risk for you?

He lasted in the army until the end, leaving only in the spring of 1991 — just a few months before the Soviet occupation of his homeland came to an end. When Toots crossed the border on his way back from military service, he did not know that he would never again go to Russia. At least, not officially.


After the failure of the hardline coup in August, Aleksander Toots went to the Paikus police school. The idea was still romantic, but it didn’t stay that way for long. In the winter of 1993, Toots was on an internship — again in Ida-Virumaa. Toots was called a “guide,” as he already knew the local people and circumstances. And so it happened that, in his first week of duty, information reached him about the whereabouts of a wanted killer. “He had poked a woman with a knife for a while,” Toots remembers dispassionately. The intern took a classmate from the academy and went to arrest the suspect. There was no fear. “I had grown up in a place where I was always in the minority,” says Toots.

A few days later, Toots got a tip that non-ferrous metal was being transported illegally. He went and helped arrest the smugglers. Both operations went into the statistics of the KAPO: a murderer and a group of criminals taken down in a week. A few months later, Toots was called to the KAPO Department. No reason was given. He went, only knowing what his boss in Ida-Virumaa, Grisha Levchenko, had told him: “When you go to the office, say ‘yes.’”

First General Director Jüri Pihl and two other officials were waiting for him. Only one question was asked. “Is Jaan Toots [a notoriously shady former high-ranking police officer] your relative?” Aleksander Toots did not respond with a ‘yes,’ instead answering that the suspicious namesake was not a relation. With that, Aleksander was employed in the KAPO. It has been almost 31 years since that fateful day. “Jüri Pihl was very picky about people,” says Toomas Sildam, who knew Pihl well. “But he trusted Sass a lot.”


Naturally, Toots was sent to his home region of Ida-Virumaa, where he lived with parents. Toots still did not have a fixed place of residence, and he did not exactly have a normal job, either. “I arrived with both hands in my pockets,” says Toots. There wasn't even a department. Everything had to be built up from scratch. Sometimes you had to take a bus to the crime scene and then call the patrol. You woke up in the morning and had no idea how the day would end. “We were adrenaline junkies,” says Toots. And besides, Estonia was a free country. That fact meant so much that it's hard for Toots to describe. In the name of this country, he was ready to do almost anything. And it seemed to him that his boss — a man named Aleksei Dressen — was ready to do the same.

Former KAPO officer Aleksei Dressen was sentenced to 16 years in prison for spying for Russia in 2012. He was handed over to Russia in exchange for Estonian officer Eston Kohver in September 2015
Former KAPO officer Aleksei Dressen was sentenced to 16 years in prison for spying for Russia in 2012. He was handed over to Russia in exchange for Estonian officer Eston Kohver in September 2015
Photo: ERR

“I've been in situations with him where I didn't turn my back and run away,” says Toots. Go poke around with Dressen? It wouldn't have been a problem for him back then. But Arnold Sinisalu also remembers another Dressen. “Shit magnet,” he says. Made all sorts of careless mistakes. One after the other. Nothing Dressen did seemed to work. Toots, on the other hand, was slowly starting to eradicate the mafia from his neighborhood.

It was hard to find a more stressful place in the 90s. Toomas Sildam even titled one of his articles as follows: “The ‘bloody autumn’ of Eastern Virumaa.” Over the course of a couple of months, almost twenty people had been killed — all members of the local mafia, who were fighting among themselves.

Toots’ special investigative interest was explosions. At that time, at least one seemed to go off every week. Bombs were even placed near schools, and Toots had to prevent the mafia civil war from affecting ordinary citizens. Together with the young investigator Arnold Sinisalu, Toots drove around, collected information, and uncovered crimes. He had a considerable network of sources — even criminals talked to him. “Important information sticks to me,” says Toots. “I walk around and people start talking. There is something in my nature that favors it.” What exactly, he doesn't say. Maybe even the man himself doesn't know for sure.

“Important information sticks to me,” says Toots. “I walk around and people start talking. There is something in my nature that favors it.”

Sinisalu remembers that even then, Toots was a certain type of person: a hard worker, always sober (this was not common at the time), determined, and most importantly, results oriented. “If he took hold of something, he didn't let it go,” Sinisalu says. Toots also made mistakes, but he was able to learn from them. Sometimes there were shootings, but he hasn't killed anyone, and he hasn't been hit either. His main tools have always been something other than brute force: psychology and theater.

Thus the Republic of Estonia gradually began to strangle the mafia to death — at least in Ida-Virumaa. Already in 1998, the president awarded Toots with the Kotkarist Iron Cross. Ten years later, Toots received the Kotkarist IV class, a token of gratitude for the full body of work he had done in Ida-Virumaa.

Then, as former Justice Minister Andres Anvelt, says, “in the second half of the ‘90s, everything changed radically” — at least as far as Toots’ role in the KAPO was concerned.


When Jüri Pihl, by then Estonia’s Interior Minister, invited Toots to become the Deputy Director General of the KAPO Board in the field of counterintelligence, Toots thought for about a quarter of an hour, then agreed. “Everything started to become too calm in Ida-Virumaa. I was up for the challenge,” he says. “The invisible enemy is even more interesting.”

“Everything started to become too calm in Ida-Virumaa. I was up for the challenge,” he says. “The invisible enemy is even more interesting.”

Toots had gained some experience working in the shadowy world of espionage while fighting the mafia — for in Russia, organized crime and the state are inseparable, and the Kremlin’s assets often operate internationally. When riots broke out in 2007 in connection with Estonian authorities’ decision to remove a Soviet-era monument from the center of Tallinn, the Russian special services did not sit idly by. Toots’ job was to prevent the riots from spreading, and the riots did not spread. Toots does not specify whether he employed the same tactics he would go on to use in 2022 when removing a different Soviet monument — this one a tank — from Narva. That successful demolition of a Kremlin symbol demanded calling potentially dangerous local elements into the station as a precaution and keeping them there until the more anxious moments had passed. Whatever methods his 2007 work might have utilized, one thing is certain: Toots plunged into counterintelligence work as if “head first into unknown waters.”

Estonian police clash with pro-Russian demonstrators in Tallinn in April 2007
Estonian police clash with pro-Russian demonstrators in Tallinn in April 2007
Photo: Raigo Pajula / AFP / Getty Images

According to Margo Palloson, a long-time member of Toots’ team, Estonia’s counterintelligence apparatus had been developing for more than ten years by the time of the “Bronze Soldier” crisis, but according to him, it was still “groping.” There were no clear goals, and more thought was given to how to recruit the enemy than how to catch its spies operating on Estonian soil. Some KGB-era technicians were still employed by the department (and one of them was eventually exposed as a traitor by Toots), but none of their Cold War operational experience had been transferred. It was also not possible to learn from foreign countries, because each has its own strategy. There is no such thing as universal counterintelligence — everyone must discover for themselves what aims and methods work best in each individual context. Thus Toots and his team set out to discover Estonia’s optimal strategies — often by trial and error. Goals were set. Results were demanded. Directions were given. And everyone got to work.

There are several metrics by which to measure the success of counterintelligence efforts, and the number of spies caught — “realizations” — is just one of them. Bringing counterparty agents over to one’s side is of course effective, but it is difficult to measure. Palloson mentions the existence of such recruitments and says that Toots and his former teammates have made several of them, but unfortunately the press never hears about these successes, and so the public largely never learns of them. What can be discussed openly is the fight against those who seek harm to the Estonian state.

Around ten years ago, KAPO contacted the prosecutor's office and proposed a legal reprioritization. Up until then, it had been clear what sorts of harsh punishments awaited outright traitors, but not all who communicate sensitive information to the adversary do so in a manner that rises to the level of betrayal. “The nature of espionage had changed,” says Toots. Now the question was whether it would be possible to bring lower level malefactors to court as well. “These were very exciting discussions,” remembers the then prosecutor Inna Ombler.

The beginning was difficult. KAPO itself had doubts as to why the move was needed. There were Western agencies that, for example, in the case of Herman Simm, did not advocate arresting him, but instead suggested an attempt at “re-recruitment.” When a smuggler was caught passing information to the FSB, the judge did not understand why the accused should be convicted. “Why can't it be like the old days, when we just deported them?” he asked the prosecutor. I ask the same. Is it the pleasure of punishment?

No, everyone on Toots’ side of the debate says. It was necessary to bring these cases before the public so that fewer people would consider cooperating with shady characters. Of course, it is not possible to get exact data about those who quit, but the gut feeling of all experts says that the move towards harsher punishments for lower level loose lips has been beneficial. The Russians have had a harder time recruiting, as potential targets understand that there is a higher probability they will be caught — and if they are caught, that they will certainly be imprisoned.

Today, the laws have been tightened to such an extent that even meetings with known Russian agents will get you in trouble. If at first even Ombler thought Toots was a little overzealous about collecting ever more fresh evidence, over time the prosecutor realized how smoothly all of the cases had gone thanks to the work of Toots and his team. Not once has any suspect even had to be kept in custody for an excessively long time: the evidence is already in place, the accusation is in court, and, like clockwork, a guilty decision is quickly handed down.

The accused himself plays an important role in the process, because when he is locked in a room with Aleksander Toots, sooner or later he confesses everything.

The accused himself plays an important role in the process, because when he is locked in a room with Aleksander Toots, sooner or later he confesses everything.


Arnold Sinisalu has never been around when Toots interrogates a traitor or spy. But he’s seen people go into a room with Toots after weeks of silence and come out having told everything. How exactly Toots does it, no one knows. “I have practiced on human souls in my work,” Toots says shortly.

When Deniss Metsavas was arrested, employees of the Foreign Intelligence Service were allowed to visit him. They entered the room, and then Metsavas was brought in wearing only socks on his feet. Metsavas felt embarrassed, and he started apologizing. Some resistance had already been broken. Later, Toots told his colleagues that this is an old trick in Russian prisons — don't torture, don't beat, but humiliate the person, and he talks.

Former KAPO chief Arnold Sinisalu says he’s seen people go into a room with Toots after weeks of silence and come out having told everything. How exactly Toots does it, no one knows. “I have practiced on human souls in my work,” Toots says shortly.

Toots himself says he does not remember this story. In fact, he categorically denies that such a thing was ever possible. He emphasizes that he does not use any methods of torture or humiliation.

Michael Weiss, the only journalist to have interviewed Deniss Metsavas, witnessed the interaction between Toots and Metsavas from the sidelines over the course of two days. “It was almost paternal,” Weiss says. “Aleksander wanted the world to know: Deniss is not a bad person, but a decent person who did a whole series of stupid things and could have easily escaped the Russian trap if he had been a little more careful.”

Deniss Metsavas (right), a former major in the Estonian Defence Forces, was sentenced to 15 years and six months in prison in 2019 for passing Estonian state secrets and confidential military information to Russia
Deniss Metsavas (right), a former major in the Estonian Defence Forces, was sentenced to 15 years and six months in prison in 2019 for passing Estonian state secrets and confidential military information to Russia
Photo: Estonian Internal Security Service

Instead of bullying, Toots speaks, understands, discusses, and thus creates a common warm nest in the soul for himself and the victim. This method works so effectively that not only have the traitors pretty much told everything, but some of their psychological tissue is now in Toots’ hands. The public knows one very exceptional case in which a traitor was convicted in Estonia, exiled to Russia, but later returned to Toots like a prodigal son asking for asylum. According to one source, something similar has happened more than once. Toots arrests someone, he manages to get what he wants, but the relationship doesn't end there. Instead, the interrogator and the interrogated are forever joined by some kind of Faustian transaction.

“In our work, psychology is one of the most important instruments,” says Toots. Closing his eyes for a split second (he does this often) and changing his posture briefly (he does this very rarely), he is only willing to betray his methods enough to say that his greatest weapon is often compassion. The opponent feels that he is at least understood — a someone both seen and heard. Toots is known to keep his promises, but it must also be noted that he is a man who, it has been said by not a few, “enjoyed breaking people in his work.” He describes himself as a person with “many vices and non-existent virtues.”

Toots is known to keep his promises, but it must also be noted that he is a man who, it has been said by not a few, “enjoyed breaking people in his work.” He describes himself as a person with “many vices and non-existent virtues.”

“It is believed that the arrested person is so tense that he wants to tell everything from his heart,” says Inna Ombler. “But it is not like that.” Toots’ preliminary work when “breaking” a person — and he says so himself — starts from the moment when the first questions about a suspect have begun to be confirmed. Toots then turns not to a psychology textbook or the penal code, but to a horoscope. The zodiac sign — says one of Europe’s most important spy hunters — can tell a lot about a person. For example, he gives a hint to future counter-spies that it is worth paying special attention to Scorpios, as finding compromise with them is difficult.

“You can often talk to him about esoteric topics,” says one of Toots’ colleagues. Toots has not received any professional education or training on how to unmask people. He hasn't listened to lectures at a university or taken FBI tutoring classes. His development instead depends on life experience.

“In 30 years, I have not had the feeling that all people are the same,” Toots says, emphasizing this point repeatedly. Yes, traitors are often very emotional people, but each case is different. There are no patterns. Details matter. No one should be underestimated. This is very important: you have to take the person seriously. You must not lie to them. Your interest must be sincere, because falsity will show itself right away. “He would even smile at the enemy if necessary,” says Estonian politician and writer Andres Anvelt, who created a character based on Toots — Tank — in his “Traitor” series. “He is a man of honor and a man of his word with these villains,” says one source. And it works. Many cases of crimes against the state have resulted in plea bargains, meaning that people have confessed their guilt themselves. And those who don't go that route nevertheless share so many details with Toots that they are all convicted anyway.

“In 30 years, I have not had the feeling that all people are the same,” Toots says, emphasizing this point repeatedly. Yes, traitors are often very emotional people, but each case is different. There are no patterns. Details matter.

But KAPO is interested in more than just a conviction in court. They want the whole story: the names of agent runners; who met whom, where and when; and anything else that might be relevant for protecting Estonia’s national security. “If you break a person, you get 90% of what you need,” says Toots. No one offers information for free, and often it is necessary to go forward with an arrest simply in order to find out all of the details, even if the initial picture is still less than clear.

Sometimes the story turns out to be smaller than expected — sometimes it is much, much bigger — but the public only gets to know a fraction of what law enforcement uncovers. “We put fewer things in criminal cases than we have material for,” says Sinisalu. Not everything can be publicized. Much of the work is, by its nature, secretive. For example, the late Edgar Savisaar, a former Prime Minister who went on to found the Russia-friendly Estonian Centre Party, offered his favors to Moscow for money, it is known, but only some of the details have been made public.

Although counterintelligence approaches have evolved over time, everyone I talk to confirms that the importance of interrogating people remains paramount, and interrogations require a certain type of character. “Sass has a very good intuition about people,” says Sinisalu. “He is a very good reader of people,” adds Ombler. “He is an engineer of human souls,” says Margo Palloson, who has sunk into a slightly uncomfortable armchair. Already while working in Ida-Virumaa, Toots began to break, tear, rend people's souls. “Man is a very complex piece of machinery,” explains Toots. “Getting to know him is a complex process. But everyone can be broken.”

The last time Toots went to the theater was many years ago, and he left halfway through — compared to the acts he routinely pulls off, the show on stage was simply boring. Writers write about the filth of the human soul. Artists paint dark urges. But Toots has been looking killers, traitors, bomb-makers, spies, and thieves straight in the eyes for decades — and he's starting to feel sad.

Why did they do that? Why did they betray their country? Toots can be black and white and uncompromising with his colleagues, but when he interrogates someone, he genuinely sympathizes. “I don't enjoy it when someone is sent to prison,” he says. But when I remind him that Herman Simm has now found God and is serving as a priest, Toots shakes his head. “Don't be fooled,” he cautions. “Simm was laughed at for a long time, but Simm was actually laughing at us instead.”

When I ask if he trusts anyone at all, Toots repeatedly replies that it is impossible to live without trust. He trusts his parents and loved ones the most, because “they never wish you harm.” But when I ask if he trusts anyone in KAPO one hundred percent, he just keeps silent.


After the capture of Aleksei Dressen, “our way of thinking changed,” Palloson says. “We started to build up counterintelligence more systematically.” Toots has noticed that now, when yet another spy is caught, it barely breaks the news threshold — and in some ways, that's a good thing. “It means catching someone is not a one-off success, but a systemic one,” he says. But “systemic” does not mean “stable” when it comes to counterintelligence. The ability to constantly change, adapt, improvise, and surprise are necessary traits. “We have to fill our gaps not with budget, but with ingenuity,” says Toots. “Opposite us is a rich and sophisticated Russia, yet we still catch their spies.”

In any case, the strategy of Aleksander Toots and his colleagues appears to be working. “Our counterintelligence is appreciated,” says current Defense Minister Hanno Pevkur, who has had enough interaction with foreign colleagues to know of what he speaks. “I cannot comment very much on how much we have been able to prevent crimes in addition to exposing foreign agents, but we are looked well upon internationally,” he says. KAPO even educates Western services on how to counter threats posed by Russia.

A Lithuanian counter-intelligence specialist — whose name I do not know and whose face I will never see — lets it be said through intermediaries that he has had a lot of contact with Toots, whom he calls “one of the brightest individuals in the counter-intelligence community of our region.” According to the Lithuanian, Toots’ deep experience, professional perseverance, and leadership qualities have greatly contributed to the current reality in which it is very uncomfortable for Russian intelligence to operate in the Baltic states. “A sincere colleague and a reliable partner,” he adds. I don't hear anything more from him.

Michael Weiss, one of the best-informed journalists on Russian espionage, has heard from more than one former or current U.S. counterintelligence practitioner that Toots is a “legend” in Washington. According to one CIA officer based in Moscow, the yearbook of the KAPO is read “like a Bible” — albeit a holy book that “names and shames” Russian agents of influence. According to the CIA, their hands are too tied by bureaucracy to achieve what Toots has. American counterintelligence is politicized — they cannot be like the Estonians, and this makes them bitter.

“Toots is an extremely impressive person,” says Edward Lucas, one of the top connoisseurs of European intelligence history, before adding only that, “I would not comment further,” Dan Hoffman, who arrived in Estonia in the 1990s as a high-ranking CIA officer and immersed himself in his work so thoroughly that he learned the local language perfectly, has known Toots for over 25 years. In a recent podcast, Hoffman describes his old colleague as “exceptionally skilled” and the KAPO counterintelligence service on the whole as “elite.” (However, Hoffman also does not wish to comment further).

Estonia’s strategies have proven themselves effective, which is why its templates have been adopted elsewhere — at least so far as other countries’ laws and customs allow.

Estonia’s strategies have proven themselves effective, which is why its templates have been adopted elsewhere — at least so far as other countries’ laws and customs allow. In Latvia, it was long difficult to prosecute those accused of crimes against the state, but not anymore. The same has happened in Lithuania, Poland, Germany, Finland, and Sweden. “It cannot be said that it happened only because of us,” says Sinisalu. “But we have had some influence.” It's no wonder, then, that Aleksander Toots can feel confident.

In some people's opinion, too confident.


“Toots has the attitude that he does everything well and correctly,” says Mikk Marran, the former director of Estonia’s Foreign Intelligence Service. “And 95% of the time, he does.” Margo Palloson remembers Toots’ uncompromising nature well. “It created tension,” he says. “When the skis are crossed, reconciliation takes time.”

Arnold Sinisalu got along well with Toots — and there are those who don’t think that was necessarily a good thing. Sinisalu has heard stories that he was overly influenced by Toots, but he himself believes that the two were simply similar, both professionally and in terms of values. “We are both interested in the result,” he says. “There has to be an aim.” According to Sinisalu, those who call Toots harsh and unjust may even be right, as “he has a great responsibility.” Often, only Toots and Sinisalu knew the whole story behind some incidents at KAPO. Sometimes, they could not even explain everything to the other deputies. Toots’ subordinates saw a fragment of the bigger picture and still had to carry out the order. Naturally, this also caused tension. “There is his opinion, and there is a wrong opinion,” says Sinisalu. His colleagues say Toots can be abrupt, passive-aggressive, even mean — depending on the interlocutor and the circumstance. “He is efficient and sharp, in many ways,” says Lavly Perling, Estonia’s former Prosecutor General. “He has great inner pride,” adds Kaimo Kuusk. “He won't ask for anything.”

“I'm a Sagittarius,” Toots says. “A Sagittarius worships no one. His element is fire.”

This characterization is largely confirmed by Toots himself. “I'm a Sagittarius,” he says. “A Sagittarius worships no one. His element is fire.” One cannot speak of friendship in this profession. “He always has a role and a mask,” says Palloson.

“I'm not a diplomat,” says Toots. At one of our meetings, he accidentally sits at the head of an important table, but immediately changes his place — he doesn't want to be the center of attention. “Sass’s specialty was that he shouldn't have done many things as a boss, but he wanted to,” says Palloson. For example, Toots went to arrest Simm himself. He was there when Dressen was handcuffed and Deniss Metsavas was arrested, because “immediately shaking him up was important,” according to Toots. “And I didn't want to lose my form,” he adds. “Someone has to take responsibility when something goes wrong.”

When the team came back after these successes, they celebrated. The participants of the operation were praised and thanked. Afterwards, Toots went to Sinisalu and asked him to distribute the rewards, with Sinisalu suggesting that the team members may not even have known about the potential for a performance incentive. “His bar was high, but it has to be,” says Palloson.

Palloson has learned a lot from Toots, but what exactly, it is difficult to say. A knack for gambling successfully? The ability to distinguish the truly important from the seemingly important? Instinct? Knowledge of human souls? High energy levels? Palloson lists these as attributes of his boss that cannot exactly be transferred. There are those who say that Palloson has tried to stay away from some of Toots’ character traits as a leader — he allows subordinates more freedom, does not punish mistakes so mercilessly, sympathizes with his own side more easily. Because there are also those who say that Toots’ complex nature has made not only his direct professional relationships difficult, but has also worked against the unity of the Estonian intelligence community in general. “He has a tough attitude and speaks sharply,” says Mikk Marran on the phone during a run. “His nature makes cooperation difficult.”

In the past, cooperation between Estonian counterintelligence and foreign intelligence really was strained. Years ago, there was competition for information — good information is worth its weight in gold, and everyone wanted to keep it for themselves. There was an instance in which the employees of the Foreign Intelligence Service (then the Information Service) tracked down five culprits who had stolen a large amount of money, but KAPO was called in to investigate nevertheless. Toots says that the leadership of the Foreign Intelligence Service was interested in reducing the strain that episode caused, but in any case, harmony was not restored. “There was no great love between the two houses,” says Kaimo Kuusk.

But in the last ten years or so, relations have notably warmed up. According to Kuusk, it all started when foreign intelligence went to KAPO “with a real scheme, which they were able to pull off with a very good result.” After that unnamed example of cooperation, the organizations no longer sought to compete, but instead began sharing information. “Our cooperation went very well,” says Marran. KAPO even gave the Foreign Intelligence Service a specialist who built up a whole “collection area” for his new house, and the teams loaned one another specialists when their expertise was needed to perform some task. “We've grown up,” says Toots.

But that didn’t mean the Foreign Intelligence Service enjoyed its interactions with the “legend” over at KAPO. It's true, Marran says, that he communicated most of all with Sinisalu, who was very cooperative. Kaupo Rosin, the current head of the Foreign Intelligence Service, declined to comment for this article, as did his deputy Tarmo Türkson. However, according to Margo Palloson, the cooperation is still going smoothly. When I ask whether this is thanks, at least in part, to the fact that Toots has announced his departure, Palloson declines to answer.


The year was 2015. Estonian Internal Security Service officer Eston Kohver had just been recovered, and the press did not know it yet. Toots sat down in an office together with Kohver, the then Minister of the Interior Hanno Pevkur, and Arnold Sinisalu. It had been a long and arduous process, and Toots does not agree with those who say that the Russian special services violated some sort of unwritten rule by kidnapping Kohver. “It was a victory for their work,” he says.

Eston Kohver at a press conference in Tartu after his exchange for Russian spy Aleksei Dressen on September 26, 2015
Eston Kohver at a press conference in Tartu after his exchange for Russian spy Aleksei Dressen on September 26, 2015
Photo: ERR

And Estonia’s loss. Although Toots never confirms it, it seems that the Kohver case was one of the most exhausting of his entire career. “He has four children,” Toots notes once. In several encounters, I raise Kohver with the utmost care imaginable, and each time Toots’ attitude becomes stiff and unfriendly. He doesn't talk about it himself, and he forbids anyone the chance to meet with the since returned Estonian officer.

“The kidnapping of Eston was our systemic failure,” says Arnold Sinisalu. It was Sinisalu who decided, after discussions, that Kohver could go to the border to “do business.” He expected the Russians not to make certain moves, but given what they had already done, “it was stupid of us.” It was thought that there were still some unwritten rules, and it was not taken into account that the Russians were so desperate to get Dressen exchanged, they would be willing to abduct an Estonian officer on Estonian territory. “Yes, I regret it,” says Sinisalu.

The negotiations were difficult. Of course, no one will say where, how, or with whom they talked, but when I once asked Toots whether he had ever met his opposite numbers in real life, he only half-evasively said: “Everything has happened in life.” The Russians came to the talks with bravado, Margo Palloson recalls, using body language indicating that they initially wanted much more than just Dressen. Toots negotiated. He chose his words carefully. In such situations, even the wrong joke can turn everything upside down. “In our work, the game is about human souls,” he says several times. He avoided anger against Dressen, kept his cool. “It was a shock when the first conviction came against Dressen. He destroyed the work of many of our people,” says Palloson. “But after that, the head started to work coolly. You have to learn what to use up your emotions on.”

Then the breakthrough occurred. Estonia got what it wanted — namely, Kohver — and the Russians got much less than they had been demanding. The handover took place on Dressen's birthday. Symbolism is important there. “Byzantine sh*t,” says Sinisalu. Toots traveled to the bridge at the border while Dressen sat in the same bus. “What could he have felt at that moment?” asks Toomas Sildam again.

The handover between Russia and Estonia took place on Aleksei Dressen's birthday. Symbolism is important there. “Byzantine sh*t,” says Arnold Sinisalu.

Wasn't he afraid that now the Russians would come for him instead? “Sometimes the word means something,” says Toots. “I treated it with cold composure.” But when Dressen wanted to reach out to Kohver on the bridge, Toots quickly pulled them apart. “We don't shake hands with traitors,” he says. There was no need for a snapshot in the media: the traitor shakes hands with our man as if they were equals. Then Dressen went. Toots makes it clear that the traitor is still being watched — “Dressen knows well what it means for him if he becomes a danger to Estonia,” he says cryptically.

Then there was the return trip to Tartu, where the four figures sat in the office and discussed how to tell the press about it all. “I saw that it was a great release for Sass when everything was resolved,” says Pevkur. The conversations dragged on and some kind soul asked what to bring for food. Toots thought the occasion deserved a little celebration — please bring us a cake. A marshmallow cake was delivered. Toots took a small fork and slowly began to eat away. When he plays it back to me, he exudes a simultaneous sense of weariness and relief. In the office, his thoughts drifted a little, and the others carried on the discussion while Toots’ fork slowly worked the cake until only a small slice remained.

When Dressen wanted to reach out to Kohver on the bridge, Toots quickly pulled them apart. “We don't shake hands with traitors,” he says.

Aleksander Toots has never smoked, and on the day after the going-away party, his meetings start early in the morning — as he hasn't had a drink, either. But he can put away sweets in large quantities. Kaimo Kuusk remembers dinners where Toots ordered two desserts to end the evening. Toots smiles when he hears this. Yes, sugar is what relieves his stress. Perhaps this is also the reason why the only colors in these Kafkaesque concrete labyrinths of the KAPO are the colorful wrappings of assorted Kalev candies.

Stress is an integral part of this profession. The goals here are clear, and if they are not achieved, it spells disaster for the nation. The opponent is huge, sophisticated, and angry. One constantly has to think up new means of solving problems, to disrupt previous patterns, to don a fresh mask. After all, a traitor could be working right there in the office next to yours. And if you do achieve any sort of professional victory, the accomplishment must usually be kept secret.

The requirements of secrecy can be inspiring, but also exhausting. “We all have a repressed vanity,” Kaimo Kuusk says. Important work is being done, the press is snooping around in an attempt to hammer out details, but all the officer responsible for the successes can do is to look off into the distance while declining to comment on any of it. Kuusk himself has been working as an ambassador for the last few years, first in Ukraine and now in Lithuania, and he laughs that he is living out his spy's vanity in such a way: receptions galore, attended in a tailored suit and a silk handkerchief folded into a triangle peeking out of his jacket pocket.

Toots seems quite indifferent to such spectacles. “I'm not interested in the facade,” he repeats over and over again. He does not agree to take photos for this article, and there is no point in asking twice. He does not name those who could speak about him, and he refuses to convince any of his acquaintances to go on the record. A certain professional pride seeps into Toots’ words — and his pauses — as if he wants to say something more, but cannot. “I have never sensed that he wanted to brag about his achievements,” says Toomas Sildam. There must be a valve somewhere that allows Toots to gently release all this tension and suppression. But where?

A few weeks before the release of Eston Kohver, during the most critical period of the ordeal, Toots went on an extreme run, where he had to traverse, among other surfaces, sea water. He has run around Estonia’s various lakes and monasteries and mining towns. Over the decades, the Estonian press has published very few interviews with KAPO’s legendary counterintelligence guru — but dozens of news items about the new achievements of recreational runner Aleksander Toots. Once he ran several dozen kilometers while wearing a 15-kilogram backpack. “At that moment, the closest competitor realized that he doesn't like mountains after all. But for me, the harder the track, the better,” Toots said of that particular feat. Erik Gamzejev remembered how Toots comes to the start and complains that his back is aching, his leg is throbbing, he hasn't had time to train — but again and again, he somehow manages to make it to the finish line first. “The cunning of the spy,” Gamzejev marvels.

Toots runs in the mountains and by the sea. He runs five kilometers, a half-marathon, a full marathon, and if necessary, he spends 24 hours in a stadium and runs more than 100 kilometers at a stretch.

“The first 80 kilometers were relatively easy,” he says once. “I felt very bad,” he comments after another such manic run, “but I suffered through.” A few weeks later, he runs his next marathon.

Toots runs in the mountains and by the sea. He runs five kilometers, a half-marathon, a full marathon, and if necessary, he spends 24 hours in a stadium and runs more than 100 kilometers at a stretch.

Toots says he runs at least ten kilometers every day. At least once, he goes for a run in Narva the day after eating two desserts. There are those who say that Toots always has a track suit at the ready. At his going away party, there are admonitions for the new pensioner to preserve his sanity by running, but one doubts those words will land on fertile ground.

This kind of mindless running has little to do with fun. “You learn your limits,” says Toots. You move them in every way. You know that you can still squeeze a little extra energy and endurance out of somewhere. “There are a lot of resources in a person that he has no idea about,” he says after a race that lasts 24 hours.

Toots giving a rare interview on camera after finishing second in a stadium marathon in 2015
Toots giving a rare interview on camera after finishing second in a stadium marathon in 2015
Photo: Screenshot / Rene Kundla / YouTube

When there is no running to be done, Toots goes to the country and does almost anything he can there. He builds. He carves so enthusiastically that a colleague affectionately calls him a sculptor. He digs the ground. He recently felled several fir trees and showed photos of his handiwork in the office, describing the proper methods in detail. His eyes were shining.

“Psychologically, this work eats up a lot,” says Toots. “Karma has done human experiments on me.” And the effects of those decades-long stressors do not magically disappear at retirement. “You could still see him running from time to time with his phone to his ear,” writes one reporter. “The calls I had to take kept coming,” Toots admitted. Even when he skis, the phone is next to his head.

“Psychologically, this work eats up a lot,” says Toots. “Karma has done human experiments on me.”

Toots sleeps well, but in his sleep everything can start to turn. Once he shot a wanted man four times in a dream, and when he woke up, it wasn't long before the guy came and turned himself in. “Sometimes I feel like I can't get out of this role,” says Toots.


Aleksander Toots has communicated with many Russian intelligence figures — seen them face-to-face somewhere, somehow. There was no particular sense of hatred between them. On the contrary, “they, too, are specialists in human souls,” says Toots. “You will always find a common language.” Sometimes one is best understood by their greatest adversary.

For the past 16 years, Russian intelligence has certainly kept Toots busy. No other antagonist has provided as much inspiration as big, sophisticated, angry Russia. But “I don't care how strong the opponent is,” says the counterintelligence legend of tiny Estonia.

Size, of course, isn’t everything. The Russians, for their part, have said that the great trump card of the Estonians is their calmness. “Your advantage is that you make decisions with a cool head,” one of them is said to have told Toots at one mysterious meeting or another.

Toots observes the Russian cultural space every day. He watches their news, scours the Internet for a few hours, immerses himself in today's version of Kremlin myth-making. Toots constantly puts on Russian music at home, listens to 90s-era rock, and in this way keeps his finger on the pulse of Russian life. “I have no one to talk to about Russian bands,” he complains. Thanks to this obsession, Toots knows the vernacular, and through it the general state of mind of its native speakers. When it comes to interrogating them, Toots can meet them on their level.

“I have no one to talk to about Russian bands,” Toots complains. Thanks to this obsession, he knows the vernacular, and through it the general state of mind of its native speakers.

“You have to understand Russian culture, history, and language, because if you understand them, you will not underestimate them,” says Toots. A sense of superiority has no place in counterintelligence. “Everyone lies to everyone, this is a special feature of Russia,” says Toots before quoting the Russian proverb, “If you don't cheat, you don't live.”

But this does not mean that one can be arrogant towards the Russians, thinking that their emotional unpredictability and gamblers mentality somehow render them harmless. Instead, it is necessary to know the opponent, to understand him, to be able to negotiate with him in any situation — “if you go in with the expectation that they are the same as you, you will be deceived.”

“Everyone lies to everyone, this is a special feature of Russia,” says Toots before quoting the Russian proverb, “If you don't cheat, you don't live.”

When I ask Toots if the public would be worried were he to tell everything he knows about the desires, reach, and plans of Russia’s espionage arms, he nods. “Very worried,” he says with his characteristic brevity. According to Toots, however, it doesn't pay to be too afraid. “If you are ready, there is no problem,” he says. When I ask if he expects any form of personal revenge from the Russians, he says only that, “I have been in different situations. I've been lucky.”

The Russians are fully aware of Toots’ identity — they have let him know that they know the names of his wife and children, which they received courtesy of an Estonian traitor — but he doesn't feel fear. “I take a philosophical approach to it,” he says. Philosophy features frequently in the lexicon of Aleksander Toots. Its meaning is something akin to: let's not be emotional, let's not be afraid, let's not be nervous, because life will fix everything by itself. Life, and nothing else. What has been has been. What will come will come. “I don't regret anything,” he says.


Last spring, member of parliament Üllar Saaremäe met an old classmate by chance in the courtyard of the Riigikogu, Estonia’s legislature. They hadn't communicated very closely after leaving school. When Saaremäe started playing a cop in the TV series years ago, he briefly called Toots to ask how real world police work compared to the on-screen version. Saaremäe thinks he remembers that Toots smiled on the phone. “It's not that easy to get someone to confess right away,” Toots is said to have said. “You must wait for that.”

The Riigikogu, Estonia's parliament
The Riigikogu, Estonia's parliament
Photo: Visem / Wikimedia Commons

At the Riigikogu Toots told Saaremäe that he would retire soon. The decision had been made, and the summer house was already waiting. “Are you going to drink beer and go fishing?” Saaremäe asked. “I haven't learned the first one,” Toots replied, and left.

However, Aleksander Toots says that he is not planning to retire, only that there are now more “things” to be done. One of them is probably travel. “I would have liked to go around the world,” says the former maritime school student. “I hope he doesn't fly over Russia,” Toomas Sildam says with a slight smile in his dimly lit office.

As for what exactly comes next, Toots won't say. “The Sagittarius element is fire. I live a mobile lifestyle,” is the most he’ll offer up. “Stability and routine exhaust me.” In any case, Toots will not be sharing comments in the press as a “security expert.” According to the man himself, “I'm not an expert, but I have experience. In this field, experience is the greatest expertise, and everything else is just talk.” It has indeed been a very busy life, very exciting, but Toots is not going to write a memoir. Most of the most important elements could never be included anyway.

“Whatever he's going to do next, we'll know when we know,” said one of Toots’ subordinates recently. “If we try to start figuring things out ourselves now, we will only be deceived. He’s had a plan B ready long ago.” Still, one could be forgiven for predicting that Toots does not intend to completely turn his back on KAPO, or on Estonian national security. “I am not indifferent to what happens next,” he says. “These people have put their work and health into this. I wish them well.”

When I ask Toots what he's most proud of, he doesn't think twice. “For the fact that I have been lucky enough to work with such a team.”

When I ask Toots what he's most proud of, he doesn't think twice. “For the fact that I have been lucky enough to work with such a team.” He talks at length about team spirit as if they all share the same blood. He speaks of trust, of how his coterie has experienced both the brightest and darkest of times together. According to Inna Ombler, who has worked in the prosecutor's office for over 25 years, the Toots team was without a doubt the best she has seen. Not only were they specialists in the field of intelligence, they were always ready to look for more evidence in order to mold the information they collected into the right form for presentation to the court. “Our collaboration was fascinating,” she remembers. “Sass had made reliable choices. He is a team person with the badge of a leader.”

However, his teammates are not his friends. “It's a generational thing,” says Sinisalu. In the older generation, results were demanded at any cost, and a wall of separation remained fixed between personal and professional life, allowing bosses to be more demanding. “It was a clear choice,” says Sinisalu, who now lectures at the university. And yet Toots keeps coming back to how “it's all been thanks to the team,” about how they never forget their common blood. “I don't know how the new generation can adapt to the tricks that the Russians use,” says Andres Anvelt.

“There are no irreplaceables,” Toots says at our last meeting. Estonia can manage without him. The legend goes, but the institution he helped build remains. Besides, times are also changing in counterintelligence. Technology has made progress. There are cyber tools. Mass data processing. Still, “working with human material” will always be a critical part of the task. Tearing people down was what made Toots Toots — and the need for his very specific skill set will never go away. “They could invite him to the interrogations,” suggests Kaimo Kuusk.

When I ask what he recommends to his successor, Toots thinks for a moment before quoting a famous line from Estonian literature: “the best letter of recommendation is the man himself,” he says with a smile.

Then I ask who or what decides what his legacy will be in the history of Estonian security. Toots smiles again. “Time,” the former head of Estonian counterintelligence offers an answer that says it all.

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