According to a classified 141-page NATO report, Simm is the one spy who did the most damage to the transatlantic military alliance. As a former Soviet militia member, Simm rose in a few years to become head of the Police Board of newly independent Estonia in 1991 but he was discharged in 1995 for spending the agency’s funds too loosely. After being sacked, Simm took a post as an unglamorous head of office at the Ministry of Defence, but was quickly promoted to head of the department responsible for protecting state secrets. In 2001, Simm was also named an Estonian security envoy to the European Union and NATO. There he had unrestricted access to not only Estonian secrets but to those of NATO – right up to 2006 when he unexpectedly stepped down, citing nearing retirement and poor health. But Simm did not leave the ministry – he continued to draw a salary as an adviser to the minister.
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During his career as a spy which lasted over 12 years, Simm passed thousands of documents containing Estonia and NATO secrets to Russian intelligence. He met with his handlers mainly outside Estonia; and Estonian security officials only got wind of Simm’s activity after they were tipped off by their Western colleagues. American counterintelligence had taken an interest in a resident of Spain, Antonio Graf, who posed as a Portuguese businessman of Brazilian descent. Graf turned out to be Simm’s contact – Russian intelligence agent Sergei Yakovlev.
Estonian security officials worked together with their Western counterintelligence agencies to gather the evidence they needed try and convict Simm. Simm’s long-time role as the steward of the Defence Ministry’s most highly classified documents was humiliating for the Kaitsepolitsei, the Estonian national security agency. Understandably, the agency wanted to cleanse itself of this stigma by mounting an immaculate operation to arrest Simm and bring him to justice.
Simm was arrested without a struggle. The transcripts of his interrogation remain classified, but it seems he quickly yielded and came clean before his interrogators. He pleaded guilty in court in February 2009 and was sentenced to 12 and one-half years in prison.
Even though the details of how Simm was recruited and his betrayal of Estonia are fairly well known not just to the Kaitsepolitsei but to the Estonian public as well, some questions still defy easy answers. How was it possible for a former member of the Soviet-era military recruited as a KGB agent in the Soviet era to enjoy such a stunningly quick rise through the ranks in the most sensitive department of the Estonian Defence Ministry? And how could the national security agency, which performs painstaking checks on all officials whose work involves state secrets, fail to notice a spy working right under their noses — for 10 years — at the top of the Defence Ministry’s Security Department?
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The answers to these questions lie not only in the present but in the past – from when Estonia was freed from Soviet power and established its own intelligence and counterintelligence organizations as an independent country. The KGB had recruited Simm as a covert operative back in 1985 under the deep, dark occupation when there was no sign independence would ever be restored. After Estonia did become free again, Simm’s KGB ties went dormant. It was only in 1995 that the relationship was renewed, after Simm had been fired as police director and, nursing a grudge against the government, accepted a post at the ministry where he was contacted by Russian intelligence on a trip to Tunisia and recruited again. Simm was in part motivated by fear that Russia might expose him as a former KGB collaborator.
In the late 1980s, there were over 1,000 people working at the Estonian SSR KGB. About half were operatives, who had a total of 4,000-5,000 secret agents plus thousands of informers and other helpers. While Latvia and Lithuania managed to end up with a large number of their KGB documents, the archive shelves in Estonia were bare. In autumn 1989, two years before the Soviet Union crumbled and Estonia regained independence, the KGB removed over 13,000 former agents’ files from Estonia to Russia. In spring 1990, another 4,500 active agents’ files were taken away. Estonian authorities were given only equipment and unimportant documents, which for the most part did absolutely nothing to identify the KGB’s collaborators.
To cleanse society and remove from power those who had supported the occupation forces either openly or covertly, Estonia adopted the Oath of Conscience Act in 1992. Under this piece of legislation, those formerly in the employ of Soviet intelligence and security were barred from running for office or holding high state posts. Up to the year 2000 all those who sought such a position had to swear an oath that they never worked for Soviet intelligence or security agencies. Those who perjured themselves faced criminal prosecution.
Unfortunately the law did not accomplish much, as it was impossible to verify the oaths of conscience. Only a few false oaths were exposed on the basis of secret testimony from some former KGB agent or documentary evidence was found from some seemingly unimportant piece of paper that the KGB had inadvertently failed to destroy. But no truly important documents, including agents’ files, are in Estonian hands. Instead, they are in Russia's possession.
Consequently, unlike Estonian counterintelligence, Russian intelligence knew a great deal about the concealed past of prominent people in Estonian society and could use that knowledge to influence them. Hermann Simm was one such person. When he took the post of police prefect in 1992, he unhesitatingly swore his oath of loyalty and became easy to blackmail later due to the threat of criminal prosecution.
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Both the Kaitsepolitsei (responsible for national security) and the Teabeamet (foreign intelligence) were established from the ground up. The first Kaitsepolitsei officials were university students in the upper classes of the University of Tartu’s law and history faculties, led by former, experienced criminal investigation police official Jüri Pihl. Although hiring former KGB personnel wasn’t prohibited by law, there was a fundamental opposition to such a practice at the Kaitsepolitsei. It wasn’t just the lack of trust – the public image of the agency was at stake. After 50 years of occupation, the people had no tolerance for even the mere shadow of the KGB. When Pihl hired 14 people who had formerly worked on the technical side of things at the KGB, specialists in wiretapping and the like, a major scandal broke out. Due to the lack of experienced personnel it would be years before the Kaitsepolitsei could effectively do its job of watching over national security. What it did succeed at was building an organization with a clean, good reputation, which continues to be an effective force, at least in the battle against corruption.
The Teabeamet, the Estonian intelligence agency, made an even more modest start in 1992. Three young men – the lawyer Ants Frosch, a final-year history student and a computer software specialist, none of them with any intelligence experience – spent their first days on the job by sitting in the agency’s lone office, perusing books on intelligence ordered from foreign libraries. Their job was to set up Estonia’s intelligence service so that it would be completely cordoned off from anyone who had even indirect ties to the KGB.
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By September 1992, the fruits of these three men’s labour was published – a document, classified to this day, entitled "Basic principles for developing the Estonian secret services". The basic points of the document dealt with oversight mechanisms, parliamentary oversight, keeping operations separate, prohibiting the use of intelligence for domestic political purposes and so on. One unconditional requirement was to avoid the development of a monopoly on information. Intelligence was to be strictly separate from counterintelligence. Of course, a solid theoretical basis wasn’t enough. Experience and expertise were the order of the day, but arriving at these qualities on one’s own and learning from one’s mistakes can be very expensive not just in the financial sense. It was soon found that if Estonia wanted to build an effective intelligence agency, it was absolutely vital to work very closely with Western agencies. Tallinn chose the British without much hesitation. As the Baltic states were of interest to the intelligence services of many powerful countries and the Estonian trump card for the West was good knowledge of Russia and Russians, it wasn’t long before the first Estonian intelligence personnel were in training at Fort Monckton. The extraordinarily close relationship laid 20 years ago continues to reap benefits today.