After independence was restored in August 1991 Simm moved onwards and upwards, becoming in early 1993 the regional police chief in Harju County, the area around the capital, Tallinn. That was one of the hottest beats in Estonian policing: as well as dealing with endemic organised crime, toxic waste spills and smuggling, his patch included a Soviet nuclear submarine training base at Paldiski, which was still out of the control of the Estonian authorities and had become a magnet for organised crime. Simm supervised the withdrawal of Soviet nuclear fuel elements and the handover to the constitutional authorities. Two months later, he became the top police officer for the whole country, where he showed a courtier-like ability to ingratiate himself with the powerful and the up-and-coming. In interviews with dozens of former associates, the adjective that comes up repeatedly is ‘helpful’. One not particularly close colleague was startled when Simm, having learned of his upcoming wedding, offered the services of a patrol car and two police officers to direct the traffic and organise parking.
In 1995, Simm moved to the Defence Ministry, initially to a low-key job as head of the analysis bureau, where he stood out as an efficient bureaucrat. The then Defence Minister, Andrus Öövel, said proudly that hiring a former police chief for the young ministry was like ‘winning the lottery’.2 Few worried when Simm then added to his portfolio the handling of classified documents. It was an unpopular job: Estonia was plagued by scandals involving missing, supposedly secret, papers. Too many items were classified and the rules for safeguarding them were onerous and badly drafted. Simm’s bureaucratic habits, honed in the Soviet era, helped him sort out the chaotic paper flows inside a still half-baked bureaucracy. Estonia’s foreign friends, keen to see order prevail over chaos, quickly talent-spotted the new official as someone worth cultivating. Britain’s government (noting that his orientation was more towards Germany and Finland than to the Anglophone world) paid for him first to learn English at an intensive course at the Foreign Office language school and then to study security policy and practice at Chicksands in Bedfordshire, the citadel of Britain’s Defence Intelligence Service.3 On his return, he was a natural choice to oversee the ministry’s move to NATO’s security standards. His efforts received high marks: drills and tests showed Estonia’s ability to handle secrets to be first class – and indeed better than in some old members of NATO.
Once Estonia joined NATO in 2004, Simm, by now the ministry’s top security official, became a still more regular visitor to its Brussels headquarters. Although slightly handicapped by his stilted English – notably better suited to meetings than social events – his affable manner marked him out as one of the more welcome newcomers. Officials there remember an assiduous networker who used slightly heavy-handed flirtatiousness to good effect when dealing with female colleagues. He was prone to self-importance, seemed to feel that he was under-appreciated in Estonia, and liked to display a vocal anti-Russian streak. At home he oversaw security clearances, promotions and transfers for the country’s most important defence and security posts. He recommended people for courses in other NATO countries, and signed off on their requests to take part.
In Brussels, NATO saw nothing unusual. Simm met every criterion for the alliance’s top-secret clearance. A similar clearance at home was issued and checked regularly by Estonia’s Kapo (Security Police).4 But Simm’s record would have repaid closer scrutiny. Why, for example, had Sweden denied him a visa in the mid 1970s? His background, the result of a brief post-war liaison between a middle-aged lawyer and a young woman, then brought up by aunts, and having multiple marriages and partnerships in adult life, could have suggested personality flaws of the kind a canny intelligence officer can exploit. A Soviet-era police officer who had travelled regularly abroad could hardly have escaped contact with the KGB. Yet Simm had declared no such thing. That should have prompted both thorough scrutiny of the files and the question of whether he might be vulnerable to blackmail. In fact, he had had his first contact with the KGB Third Department (which dealt with military counter-intelligence) in 1968, as part of a routine sounding out of all recruits to the law-enforcement organs. Had the investigators dug deep enough in the KGB files (as they did later, once Simm was under suspicion), they would have found that the Soviet secret police formally recruited Simm in 1985, and that he had brazenly denied this collaboration in a declaration in 1992.
Even his post-Soviet career was dotted with suspicious peccadilloes. These included a jackdaw-like fondness for trinkets and souvenirs, collecting caps, pens, badges and plaques and even guns. He was an inveterate junketer, collaring any foreign travel opportunities available. His political views were unusual by Estonia’s sober standards. He had a conspiratorial and eccentric worldview, prone to believe that Jews, Masons and shadowy international organisations wielded huge power behind the scenes. Jüri Pihl (the then head of Kapo) and others also recall a surprising habit of bad-mouthing Estonia to visiting foreigners. These included the late Colonel Michael Scott of SIS, who had been involved in cleaning up the mess after Operation Jungle, and retained a deep interest in Estonia, returning frequently after 1992 to visit old agents and advise on security.5 Simm cherished photographs of such meetings, particularly prizing one showing a handshake with the head of Israel’s Mossad. Though not a real intelligence officer, he was clearly attracted by the glamour of that world, and always eager for gossip and news of the inner workings of Estonia’s spy agency. Indeed, some thought he might move to a senior position there after retiring from the defence ministry. His wife claims that he was even offered a job there.
Close scrutiny of his financial affairs by a suspicious counter-intelligence officer might have followed up gifts from a generous German relative, or his rather heavy use of cash. His lifestyle, in a country where senior bureaucrats are well paid but not wealthy, was on the lavish side, with a big house in a desirable village outside Tallinn, a large Western-made jeep for transport, and a summer house and other properties to his name. (He claimed simply to make good use of his travel allowances and to have regained property confiscated during the occupation.) His unorthodox treatment of official documents should also have attracted more notice. He habitually hand-carried secret papers to NATO HQ in Brussels, claiming that only he had the requisite security clearance. But against regulations, he would stay overnight at a hotel there before delivering them. On occasion, colleagues noticed that envelopes had been opened, unwitnessed.6 But such incidents were rarely logged and never followed up. As head of security, Simm made the rules – and if he chose to break them, presumably he had a good reason for doing so. To most people, Simm was not an impressive or mysterious figure, but a friendly and amenable bureaucrat, doing a dull job well. ‘I never thought about him as the National Security Authority,’ recalls Indrek Tarand, then a senior official and now a member of the European Parliament. ‘It was just Uncle Herman doing something funny.’