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Authors: Edward Lucas

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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, describes his ability to deal with organised crime as ‘zero'. It was the steely young officers of his service (including one who later masterminded Simm's arrest) who cleaned up organised crime in post-Soviet Estonia, not the then oafish and bungling officers of the uniformed police. In
1995
Mr Savisaar – then the Interior Minister in a coalition government – again crossed swords with Simm. He recalls a ‘somewhat theatrical' red uniform ordered just for the force's most high-ranking officers. ‘Like something out of an operetta,' he says disdainfully. Simm was loyal, almost fawning. ‘Every morning he was sitting in my secretary's office eager to report – but he could not cope.' For a few months Mr Savisaar pondered how to dismiss his unwelcome subordinate. Then he summoned him and spoke of a ‘serious problem', while laying his hand on a large file labelled ‘Herman Simm' which was actually full of old newspaper. To his relief, Simm immediately resigned. ‘I was a little surprised that he then got a job at the Defence Ministry,' says Mr Savisaar drily.
bn

To be fired twice by a hate-figure is a strong recommendation. The hawkish officials of the defence and security establishment had long loathed Mr Savisaar, seeing him as a cynical and greedy machine politician with unhealthily close ties to the Kremlin. If Simm was their enemy's enemy, his foibles were irrelevant. Behind the scenes, some did worry. Security officials at the Foreign Ministry made a point of refusing to let him see diplomatic telegrams. The Defence Ministry's internal counter-intelligence service clashed with Simm on occasion, but its efforts to constrain his unorthodox habits were undermined by a conspiratorial and bungling approach: it once attempted to put several senior figures in the ministry under surveillance, supposedly as an exercise. It was easy for the self-assured Simm to arrange for such jumpy and troublesome junior officials to be fired, transferred or ignored.

Simm was a happy man as his career peaked. From his bleak and humble upbringing in the Stalinist era, he had made a successful career not only in the Soviet system, but in the one that had replaced it. On
20
November
2006
a press release marking his retirement (one of several documents mentioning him still on the Estonian Defence Ministry's website in mid
2011
)
8
gives a ghostly reminder of the esteem in which he was then held. It praises the organisation he built up as ‘effective and efficient'; and notes that he signed agreements on the protection of classified information with nearly twenty countries. The Defence Minister added that without doubt Simm had shown ‘excellent professionalism'. He also received praise from the then director of the NATO Office of Security, Wayne Rychak. Yet had any of his colleagues known the truth, they would have arrested him on the spot – for nearly thirteen years the avuncular, dependable Simm was an agent of the SVR, Russia's foreign intelligence service.

Simm was one element in the human minefield left behind in the former Soviet empire amid the collapse of communism. The nature of these devices varied widely. One kind were former dissidents, often now in influential positions, who had been protected from their own countries' secret police by their KGB connections. Some also had sincerely cultivated ties with the Soviet authorities in the belief that Mr Gorbachev's reforms offered the best chance of bringing change to their own stagnating societies. Another component was people who feared German hegemony in Europe, or who were sceptical of American intentions. Such feelings – as in Simm's case – were sometimes compounded with jealousy at the rise of smooth young Atlanticist types to senior positions. A big latent category was officials from the old regime with undeclared KGB or secret-police connections. Many of the files containing such details were destroyed after the collapse of communism (typically as part of energetic efforts by the new leaders to conceal their own collaboration). What was left behind was deliberately muddled, so that it was unclear even whether the names listed were victims of the totalitarian system, or its accessories. This created a false sense of security for many who moved on to good jobs in the new system. They did not know that before communist power collapsed the KGB had removed its own records, and copies of the most important files belonging to other agencies.

As a result, the KGB ensured that even after the Soviet empire collapsed, it, and only it, had an accurate record of who had collaborated and why. This has provided Russian spymasters over the past two decades with a unique ability to blackmail and pressurise seemingly impeccable figures in post-communist public life, who believed that their guilty secrets were forgotten or buried. Suspicions in some countries swirl around household names – heads of government or of state, ministers, newspaper editors, academics and tycoons. But the fact that such connections are even rumoured makes them less dangerous. For someone in the public eye, cooperating with the secret service of a foreign power is risky and conspicuous. Russian spymasters may gain some secrets from them, but they can exert little influence through them. More damaging are senior second-rank figures out of the public spotlight, especially in the security world like Simm. They not only know secrets, but are also in a position to cover their tracks. They are thus archetypal targets for Russian intelligence.

A
141
-page classified NATO report calls Simm the ‘most damaging spy in the alliance's history'. He unveiled the alliance's innermost secrets, from the content of meetings to the details of its most important codes. He gave accounts of the arguments that raged inside the alliance about Russia, about the relative strength and weaknesses of different countries, and psychological assessments of its senior officials.

The real harm, though, was less in the actual secrets he revealed during his time as a spy, as in the breaches of trust with the NATO alliance that arose after he was arrested. For many of the old members, Simm's treachery confirmed their worst fears about its eastwards expansion to countries that had so recently been under the Kremlin's thumb. To them it seemed that the new member states were simply untrustworthy, riddled with Russian spies and incapable of keeping secrets. The idea of a ‘core NATO' of seasoned West European members able to work closely together had never been fully buried during the alliance's expansion to the ex-communist East. The news of Simm's work for the Russians revived the discussion. For the new member states themselves the sense of distrust was different. Simm's parallel work for German intelligence (of which more later) confirmed fears of big-country machinations over their heads, not just in Estonia but also in other countries. Were German agents also at work stealing secrets in Warsaw, Prague, Budapest or elsewhere? Before Simm's arrest the idea would have seemed preposterous: Germany had presented itself as a solid ally for the ex-communist countries, always at pains to stress that its special relationship with Russia did not undermine its commitment to its immediate neighbours' security. The new members now came to believe that was a lie.

Simm's ability to operate undetected in the heart of Estonia's much-prized new security system also raised painful questions about the competence and integrity of those who should have checked him. What had the NATO spycatchers been up to? How come they had not asked Simm properly about his career in the Soviet Union? Someone of his age and background, however affable and competent, should have been a candidate for special scrutiny. Yet the checks had always been superficial. With little more than bluff, Simm had been able to escape the tightest security in what is supposedly the world's most formidable military alliance. And what about Estonia, which prides itself on keeping its security establishment free of any ex-Soviet taint? Simm was quite unlike the bright, clean-cut, English-speaking young officials who hold most of the top jobs in Estonian public service. During the
1970
s and
1980
s, they were only children. Simm was already a grown man then – and necessarily more vulnerable to KGB pressure. That should have raised hard questions, which the incomplete and misleading ‘official version' of the case leaked by Western officials fails to address. Did Simm have a powerful protector? Was his escape from scrutiny mere incompetence, or perhaps something more sinister? How was he recruited? What did he betray? How was he caught? And why did it take so long? These questions are corrosive and troubling, and have remained unanswered to this day. The answers involve not only secrets, but lies and blunders. Even Simm himself does not know the full truth, and would not (or could not) speak frankly to me about what he does know. But without his account, mine would be incomplete.

It is rare for an outsider knowingly to meet a spy, and almost impossible to meet a jailed one. Once the interrogators have squeezed their subjects dry and damage-control officers have done their work, the traitor is left to a life behind bars. Spycatchers may be proud of having hunted down their quarry, but it is also their fault that the breach happened in the first place. They may worry too that the convict will try to send a coded signal to his former masters: perhaps that he has successfully concealed some vital piece of the puzzle, or has planted a particular piece of disinformation. From the authorities' point of view, the less said to the outside world, the better. So getting to see Simm took some doing. Arrested in
2008
and jailed in
2009
, he is serving a
13
-year sentence in a maximum-security prison in Tartu, Estonia's second city. Many Estonians hope he dies there. Even my close friends in Estonian officialdom were worried by the idea that an outsider with no security clearance, writing a book that would not be vetted by the Estonian authorities, could visit the country's most notorious prisoner. Simm had outsmarted his colleagues over a period of many years. Maybe he would have some more tricks still to play. Another reason for Estonian caution was embarrassment. Simm's conviction was a brilliant piece of work by the country's spycatchers and their foreign colleagues. But the sooner the affair was forgotten about, the better for Estonia's reputation.

My counter-argument prevailed. Estonia aims to be the epitome of clean and open government. It should deal with the Simm case according to principle, not convenience. But practicality played a role too: concealing Simm would stoke conspiracy theories and look defensive. Sooner or later a Russian author or newspaper would be able to make contact with him and write him up as a victim, or hero. My book would put Simm's treachery in a broader and more informative context. The result of some hard haggling was exclusive, repeated access to Simm. An official of Estonia's security police, whom I agreed not to name, sat in on our meetings and interrupted if we strayed on to topics he regarded as sensitive (Simm seemed frustrated by this, but when I reached him later by telephone, he remained reluctant to provide any significant further information, claiming to be too frightened). I insisted that I would write what I wished: I provided no guarantee that I would submit any portion of the manuscript to any outsider; nor did I promise any veto on its contents (though I have of my own volition omitted a few names and blurred some dates).
bo
The only big point on which I failed to reach agreement, despite repeated requests, was to be allowed to make a recording of the meetings.

It was therefore with pen and notebook that in June
2009
I took the bumpy train from Tallinn to Tartu to meet Simm face to face for the first time. The prison underlines the progress Estonia has made in the past twenty years. Soviet prisons were grim, smelly and dark. Tartu's clean, light design, with smooth concrete walls and yellow doors, could be anywhere in the Nordic region. Male prisoners were exercising in the yard, with Estonian pop music blaring from loudspeakers. The sight was oddly Soviet. It took me a few seconds to realise why. In the days of the planned economies, clothing was hideous in both colour and cut. The inmates' baggy brown tracksuits, with orange stripes, were the sort of apparel you might have found in a Soviet department store in around
1985
. Then it would have been the height of fashion. Now the garb is designed to make escaped prisoners conspicuous. Yet nothing short of a military attack would spring Simm: before reaching the interview room in the high-security wing of the prison, we passed eight doors, all opened only with cards, plus two passport checks and a metal detector.

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