Zentsov was an old-style spy: a hardened KGB veteran from Soviet-occupied Estonia. While he was guiding Simm into the heart of the Defence Ministry, a new Russian intelligence presence was developing in the region, in the form of Antonio Graf, a plump, bearded man from Madrid. Apart from his slightly exotic middle names (de Jesus Amorett) he cut an unremarkable figure in the Baltic states. A Portuguese citizen, born in Brazil and working in Spain, he was one of thousands of consultants and go-betweens getting to know the continent’s new eastern frontier lands. Until 1989, West European businesses had been almost wholly ignorant of the markets and suppliers behind the Iron Curtain. Dealing with the communist bureaucracy involved marathon negotiating sessions, best conducted with strong government support. Shortage of hard currency made customers stingy; NATO controls on the export of sensitive products meant that the deals that looked most promising were probably illegal. When communism collapsed, most businesses were initially deeply sceptical about the new markets. Would bills be paid? What was the work ethic? Could the communists come back? Would civil war and chaos spread from the Balkans? What about organised crime? And corruption? Even the most basic data about household income, family structure, education levels, property rights, currency regulations and the like were unknown.
So Antonio (as he was known to his many acquaintances and contacts) sounded completely plausible in his many trips to the Baltic states, which seem to have started in the mid 1990s. He assiduously collected information about business conditions and the political and economic outlook, apparently spending some years building his ‘legend’ as a regular and credible visitor before engaging in any spying. His mission seemed anodyne and convincing. One contact recalls:
He told me that he was representing Portuguese businesses. He said: ‘It appears you guys are going to join the European Union – we want to know more about your countries.’
People who met him recall nothing suspicious, and little that was even distinctive, except possibly his odd choice of tipple: a revolting mixture of Campari and tonic. Anyone suspicious about his motives or background would have found it hard to check them. Spain and Portugal, and their languages, were all but unknown in the Baltic states in the 1990s. If his Spanish sounded faintly accented, that would be because he was Portuguese. If a Portuguese speaker noticed a stray syllable, the answer was that he was born in Brazil – which from a Baltic point of view could have been the far side of the moon. The idea that he was in fact a Russian intelligence officer named Sergei Yakovlev, working under an elaborately constructed illegal identity, would have seemed paranoid fantasy.
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 unusuaclass="underline" 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.[70] 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.