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Herman Simm, story of a Russian deep cover mole IV


For fulfilling his assignments for the SVR Simm was issued a laptop, a digital camera, USB flash drives and a pill container with a false bottom to hold memory cards. Simm's compensation package included some $1,320 US a month, topped off with $250 US for health care. During the course of his betrayal of Estonia, Simm copied, photographed and digitized thousands of documents and delivered them during 14 meetings throughout Europe or at agreed upon dead drops.

In confirming a meeting, Simm transmitted an encrypted numerical message, from a card-operated public pay phone to Yakovlev's pager. His encrypted ID number plus 55 meant the meeting could take place. Yakovlev after this was to approach him. A similar coded message meant there was a problem. None ever existed.
Herman Simm (Left)

In his job as the chief of the National Security Authority at the defence ministry Simm decided how documents were to be compartmentalized – who would have access to which documents. He managed the protection of classified material, the system transmitting secure data abroad and vetting of security offcials.

NATO's later reports assessing the damage that Simm had done concluded that Russia's 2007 cyber attacks, which lasted for three weeks and which were avenging the relocation of a Soviet monument in Tallinn, resulted from Simm's delivery of encryption technology to the SVR.

Simm was also entrusted with talent spotting, something usually left for experienced career intelligence operatives. In the recruitment process he was to find answers for some 60 questions about candidates detailing personal habits, drinking, womanizing, other frailties etc.

Making regular deliveries to dead drops, meeting SVR personnel all over Europe, directing close attention to potential recruits' life-style interests and flaws, coming from a miilits polkovnik's background – all of these aspects of Simm's life should sooner or later have attracted the suspicions of Estonia's spy-catchers. They didn't. Neither did Simm's rule-bending handling of documents. His occasional rants against the Russians probably helped mold his image as an Estonian patriot.

(That reputation undoubtedly got a head start when Simm was said to have hand-delivered hard-currency in suitcases to safety in the early years in Finland to keep them out of Moscow's hands. It also seems that being recognized by others as an Estonian patriot was of great importance for Simm.

In interviewing Simm after his conviction in 2009 Ed Lucas describes Simm's own reasons for agreeing to be an agent for the SVR. Simm insisted he was frightened. He was convinced that Russian intelligence had more than 500 poisons which they were ready to use. If they were capable of finding him in Tunisia, he wasn't safe anywhere.

But, before accepting, Simm said he demanded that he would never be ordered to do anything to harm Estonia. The SVR of course agreed. Russia was Estonia's close friend and the Kremlin's only worry was the possible establishment of military bases there from which an attack on Russia could be launched. Simm took the bait.)

Was it a cavalier attitude or a sense of ownership of the regulations governing handling secret documents that allowed Simm to habitually violate his own rules? He constantly hand-carried documents to NATO headquarters, stayed overnight at a hotel before delivering them, opened envelopes without anyone else being present etc. Nobody dared confront him with this. Simm ignored it or shrugged it off. Bothersome junior personnel could be transferred, fired or simply left unacknowledged.

Initially what Simm delivered to handlers was meagre. He was only able to supply observations about the leadership of the country, about their personal problems, who was in, who was out etc. But it was more than just shallow depictions. Since he was the Defence Ministry's security chief and responsible for vetting staff for security clearances, his questionnaire probed the subject's private life in detail – information that was valuable to SVR recruiters.

Laas Leivat (To be continued.)

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