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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.’
    Even his earlier role in the defence of Toompea Castle in 1990 was not universally seen as heroic: some Estonians there at the time believe he gave himself a nosebleed as a sign of valour. Mr Savisaar recalls: ‘He was brought before me red in the face and shivering. He gave me the impression of a coward. So we fired him.’ 7 Jüri Pihl, who worked closely with Simm,