Deception (40 page)

When Zentsov retired, it was Antonio who took over as Simm's case officer. Relations were poor from the start. Zentsov had excellent tradecraft and good people skills. Antonio did not. He was already known to Simm as a postman, handling the huge amounts of classified material that the Estonian was passing to the Russians. They had met once at a suburban railway station outside Tallinn. But Yakovlev was a curious choice of case officer for a source of Simm's importance. He appears to have broken several cardinal rules of Soviet spycraft. The cost of establishing a fully fledged illegal in a NATO country is considerable. Creating an identity for Antonio involved obtaining the birth certificate from Brazil, using that to obtain a Portuguese passport, and then establishing a convincing pattern of activity that would take him to the Baltic states when necessary. In the austere world of the KGB, his only task would have been to run Simm: meeting him in carefully chosen locations either with proper clandestine preparation, or openly in a way that fitted both men's natural pattern of activity.

But the Russian was clearly being used for other purposes too. A good illustration of his approach comes from Ivar Tallo, a distinguished Estonian official who has helped make the country a world leader in ‘e-government' – putting public administration online. Mr Tallo recalls meeting Antonio rather reluctantly in
2001
, as a favour to a friend and colleague in high office. That was nothing unusual: foreign visitors were flooding into the Baltic states as the reborn countries' economic and political importance grew. Senior officials could not possibly meet them all, and a persistent Portuguese consultant would be quite likely to be farmed out to someone less important. At any rate, Mr Tallo chose an expensive Italian restaurant in Tallinn, on the reasonable assumption that he would at least get a decent meal in exchange for his time. Two more meetings followed. Antonio quizzed Mr Tallo on Estonia's politics and economics, showing no particular interest in his specialty of e-government or associated questions of cyber-security. At the third meeting he suggested formalising the cooperation on a commercial basis. He suggested that Mr Tallo set up a company offering political and economic forecasts, for which his clients in Portugal would be prepared to pay handsomely; to underline the point he pressed an envelope of cash on Mr Tallo as an advance payment. The Estonian politely declined. He did not want to be obligated to the persistent Portuguese and found the offer of money slightly disconcerting. Truthfully, he explained that he was simply too busy to take up the offer. His interest was in e-government, not business information. Antonio never contacted him again.

The approach is straight out of an intelligence playbook. First hook the fish, then reel him in. Money creates a relationship, then an obligation. At some point the material asked for becomes less anodyne and more sensitive. Before the victim is fully aware of what has happened, he is enmeshed. Then comes the offer of still more money for really interesting information, and perhaps the threat of exposure in the case of non-cooperation. Mr Tallo was never close to that danger, and reported the encounter to the Estonian authorities as soon as news of the spy's real identity broke. Fatefully, Antonio tried a similar approach with a senior Lithuanian public figure a few years later, arousing the interest of that country's then formidable counter-intelligence service.
^bq
It remains unclear where else he tried his persuasive tactics, and with what result. As late as
2010
, Latvia's spycatchers were still following up leads dating from his regular trips to Riga. Yet Antonio was failing in his primary duty: to run Russia's key Estonian source securely and efficiently. Simm instantly distrusted his new case officer, referring to him as a
soplyak
– a derogatory Russian word for an incompetent beginner that translates roughly as ‘snotnose' or ‘wet behind the ears'.

After a botched first meeting with Simm in Cyprus, distrust turned to loathing. Simm says his case officer was ‘lightweight and arrogant': snooty, rude and worst of all careless. The Russian was greedy too. ‘When we met I would eat a small fish dish. He would have steak and red wine,' Simm recalls in a characteristically petulant aside. He assumed that Antonio was fiddling his expenses and doubted that the Russian was a fully trained illegal; his cushy job, Simm suspected, stemmed from connections not talent. That is consistent with the theory that nepotism is rife in Russian intelligence (a theory also supported by the way the lightly trained Ms Chapman gained a plum posting in the West). In his last meeting with Zentsov, Simm had complained about the new man, only to be told that Antonio was the best available: the SVR, Zentsov maintained, had only a couple of illegals in all of Western Europe.

A more tough-minded agent might have gone on strike at this, demanding a serious handler. Astonishingly, given the risks he was taking for the SVR, Simm settled for a stipulation that meetings with his case officer should be held only outside Estonia. Communication between the agent and source was simple. Simm continued to hand over his material via dead drops, using a more sophisticated digital camera, flash drives and memory cards, sometimes concealed in a pill container with a false bottom. He received, in cash, a ‘salary' of
€
1
,
000
a month, plus expenses. The two men met fourteen times in total, mostly in the Baltic region but sometimes farther afield. By Simm's account, only Germany, Norway and Britain were off limits. They arranged their sessions via a Prague-registered pager account, with simple numeric codes to send and receive messages. The number could be dialled from a public phone box. In retrospect, that might seem sloppy too. A central principle of spycraft is to make the source do nothing unusual. That would mean exchanging messages through means that seem like random variations in ordinary life: for example by using particular combinations of coloured ties, shirts and scarves. That would be necessary for Western spies operating in a police state like Russia; in the open environment of the European Union, Russian spymasters may have considered such precautions unnecessarily elaborate.

Simm's productivity rocketed as Estonia joined NATO. He was party to the inner counsels of the alliance, attending scores of security-related meetings in Brussels and elsewhere. His own clearance was impeccable. ‘The Americans checked me, the UK people checked, the Norwegians, Germans, Denmark, Finland – all services checked me,' he recalls. A big area of Russian interest was cryptographic security. Simm duly provided details of NATO's top-secret Elcrodat network, a heavy-duty encrypted communications network used for secure messaging and scrambled voice traffic. During the Cold War, with a military conflict a real possibility, such a breach would have been catastrophic. But in peacetime, with the Soviet threat long gone, it is more embarrassing than damaging: most of the secrets that Elcrodat carried were non-secrets before and after they were fed into the system. Moreover, a key principle of cryptographic security is that if one encryption key is compromised, another can be used in future. An analogy is the combination to the lock on a safe: knowing it is useful only if something valuable is inside; and once the breach is known, the combination can be changed.

In short, it would be wrong to overstate the effect of Simm's treachery on the overall balance of power between Russia and NATO. In an alliance of more than two dozen countries, security is never as tight as it seems. Among other NATO members are countries such as Greece, which have in the past proved leaky on issues of interest to Russia, and more recently Bulgaria. Given the activity of the GRU and SVR stations in Brussels and elsewhere, it is a fair bet that Russia was receiving plenty of other information about NATO too. Simm may have been a big source, but he was certainly not the only one. By Simm's own account, he gave his SVR handler only ‘two or three things that were really important' (he declines to say what they were). Paradoxically, Simm's biggest betrayal in this regard may have been to reveal that NATO (at least at the time that Simm was spying) itself had so few secrets about Russia. When the alliance expanded eastwards, it did not draw up formal contingency plans to defend its new members, on the grounds that this would be provocative to Russia, and also unnecessary, as Russia was a friendly country.
^br
America, with the support of Germany and other countries, explicitly barred MC-
161
, the top-secret NATO committee that draws up the threat assessment, from considering any potential military dangers from the East. When Poland protested about this in
2007
, NATO chiefs reluctantly agreed that a threat assessment could be drawn up – but only for an invasion from Belarus, a country roughly a third of Poland's size. NATO military commanders also quietly engaged in what they called ‘prudent planning' – sketchy desktop exercises about how in an emergency the alliance might respond to a Russian threat.

All this would have been interesting for Russia – and valuable in the (almost inconceivable) event that it planned a military attack on the new member states of NATO. But it was not what the spymasters in Moscow wanted to hear. Their interest was in portraying the West as aggressive and intrusive, justifying the xenophobic rhetoric and paranoid worldview that allowed them keep a tight grip on power and its spoils. Consistent with that would be secret bases in NATO's new members, with plans to attack Russia. Yet the harder that Simm's taskmasters urged him to find evidence of nefarious NATO intent, the less successful was his search: the secrets he was seeking simply did not exist.

Simm also provided Russia with damaging insights into the weakness of NATO's counter-intelligence efforts. These are severely hampered by political constraints: in particular Germany dislikes the idea of hunting Russian spies inside the alliance, and puts pressure on NATO Office of Security to soft-pedal investigations and not to act on the results. Details of that were most interesting for Russia's spymasters. Simm attended two NATO counter-intelligence conferences, according to the damage control report. The German magazine
Der Spiegel
asserts that:

 

At the conference held in the Dutch town of Brunssum in
2006
, a CD
^bs
containing the names of all known and suspected Russian NATO spies, as well as detailed information on double agents, was distributed to attendees. [Antonio told Simm that] the CD ‘landed directly on Putin's desk' and ‘caused quite a stir' in Moscow . . . For the coup, Simm received a
€
5
,
000
bonus and was reportedly promoted to major-general.
¹⁰

 

Simm's other betrayals were more clearly damaging. The sixty-point security questionnaire he circulated inside the ministry, ferreting out officials' hobbies, weaknesses and guilty secrets, would have been valuable information for a Russian intelligence officer looking for other potential targets. But even more interesting than this kind of information may be the rules that govern its collection. In the run-up to Estonia's admission to NATO, Simm obtained the alliance's procedures for issuing security clearances. An application is submitted, and either rejected, accepted, or (sometimes for a reason, sometimes at random) referred for further investigation. No explanation is offered. This basilisk-like stance is essential in preserving the integrity of the system. If you don't know what to lie about, it is much harder to lie about anything. NATO at the time was dealing with many clearance applications from officials in the former Soviet bloc, and had decided that it would be unreasonable to say that former membership of the Communist Party was an automatic bar. For applications from Western Europe, such political activity, except possibly as a temporary student affectation, would have been an instant bar. NATO decided that a key disqualification for applicants from behind the old Iron Curtain would be attendance at a Higher Party School. These elite courses in the communist system's internal university were attended by the ambitious and brainy, and thus a prime recruiting ground for the KGB. For a Russian spymaster trying to work out how an agent could penetrate NATO, that would be most useful information: those with Higher Party School education should either not bother to apply for a clearance, or else should see if this part of their past could be concealed.

Another use for Simm concerned Estonia's help for Georgia and Ukraine, which for much of the last decade had hopes of joining NATO. The alliance was publicly cautious about their chances, which eventually flopped at a disastrous NATO summit in Bucharest in
2008
. But a strong lobby in America had tried hard to boost their chances, not least by helping them reorganise their defence, security and intelligence services along Western lines. It soon became clear that advice from Estonia (and to some extent the other Baltic states) was particularly effective. American and British advisers knew the theory, but not the practice. Estonia had first-hand experience in judging which parts of Soviet administration were incorrigible, and which could be successfully transformed. An influential cabal of advisers in Georgia gained the nickname of the ‘Estonian kitchen', after a senior Russian official complained publicly ‘we know this kitchen'. Russia could not stop the burgeoning cooperation between Tallinn and Tbilisi. But thanks to Simm it knew a lot about it.

Simm was also useful in keeping an eye on the relationship between Estonia's intelligence agency and its NATO counterparts. The most sensitive operations were run on a purely bilateral basis. But NATO wish lists and some intelligence obtained did cross Simm's desk. Clearly, the SVR was thrilled with their agent. As well as receiving a medal in
2006
, Simm also met a senior officer – he believes a deputy director – of the SVR, in a carefully staged meeting in the western Czech spa town of Karlovy Vary. The two men walked in a park together, with Antonio keeping a discreet distance. This is standard practice in Russian spycraft when a source becomes particularly important: it allows the service to be sure that the case officer has indeed recruited the person he claims, and provides a check against embellishment, or the use of a double agent.