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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.[71] 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[72] 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.

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br The logical absurdity of this was not properly teased out: if Russia was friendly, then why would drawing up defence plans for its weak and vulnerable neighbours be provocative? And if Russia was so easily provoked, could it really be counted as friendly?

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bs I find that implausible, as even a national intelligence agency would hesitate to compile such information in a single list and distribute it internally, for fear of the damage done if it leaked. The risk of sharing such sensitive material with twenty-plus other agencies of varying trustworthiness would be huge and such a step unlikely. It is possible that this CD was a list of past Russian agents, rather than active or suspected ones. That would still be useful information for the SVR.