Betrayer and Betrayed: New Documents Reveal Truth on NATO's 'Most Damaging' Spy

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According to the classified NATO report, this act of treason has damaged the alliance severely and indefinitely. A short time later, though, Western counterespionage officials grew suspicious of Simm. Exactly why this happened is unclear. The investigations, in which both the BND and the FBI participated, began on May 26, 2008 under the code name "White Knight." Simm, who was at this time an adviser to Estonia's defense minister, was placed under surveillance.

On Sept. 16, 2008, in a blatant violation of security regulations, Simm's handler called him on his cell phone. He had never established contact so openly. During the call, Jakovlev cancelled a scheduled meeting. "I'm sick," he said during the conversation, which was being recorded by the KaPo, Estonia's security police.

Three days later, the noose tightened around Simm. For days, he had been under constant surveillance. On this particular afternoon, he and his wife drove to the Röömu ("pleasure") shopping center in Keila, a small city near their row house in Saue, outside Tallinn, to buy cake for his stepmother. He was arrested while walking back to his car. An ambulance had been parked around the corner in case Simm violently resisted arrest. But he didn't.

In Simm's country home, police found his spying equipment: stacks of classified documents, two pistols, two rifles and pieces of paper with instructions from Jakovlev, complete with the latter's DNA. Jakovlev, for his part, had disappeared without a trace, and it was later rumored that he had defected to the United States.

Sentencing

On Feb. 25, 2009, Simm was sentenced to over 12 years in prison. He was also ordered to pay damages roughly equivalent to €1.3 million ($1.7 million) and refund the government about €85,000 in salary payments.

Several houses and pieces of property were seized as collateral, including half of his country house, his share of the row house in Saue, a dozen watercolors and oil paintings, and a collection of 44 coins.

A year before his arrest, Simm had donated a candelabra to the church in his birthplace of Suuri-Jaani. The gift did not bring him any luck. Even the hope of spending his golden years as a retired general in Russia proved to be an illusion. At their last meeting, Jakovlev had informed him that his rank and the medals never existed -- and that he was nothing but a paid traitor.

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• Part 1: New Documents Reveal Truth on NATO's 'Most Damaging' Spy
• Part 2: Changing Times and (Apparently) Allegiances
• Part 3: A New Handler
• Part 4: Busted