The Estonian Spymasters

Tallinn's Revolutionary Approach to Stopping Russian Spies

The skyline of the old city center of Tallinn, Estonia. Courtesy Reuters

“We caught four moles in the last five years,” Estonian President Toomas Hendrik Ilves told me after a recent security conference in Tallinn. “That means one of two things. Either we’re the only country in the EU with a mole problem, or we’re the only country in the EU doing anything about it.”

The note of self-congratulation was nothing new for the famously garrulous Ilves, but it also happened to be entirely warranted. His small Baltic state, long one of the Kremlin’s main targets, was having an “I told you so” moment. For the past decade, Russian warplanes have routinely violated its airspace, Russian military forces have used counterterrorism exercises as a pretext for mock-invading its soil, and a notorious series of cyberattacks in 2007 that almost certainly originated from Kremlin-backed hackers degraded its digital infrastructure. 

In turn, Estonia has proved itself more prepared to stand up to Russian aggression than any other European nation. Since 2008, Talinn has hosted NATO’s Cooperative Cyber Defence Center of Excellence, and the Estonian government has been widely recognized in the West as a pioneer in cybersecurity. More quietly, however, the country has also become a leader in using old-fashioned counterintelligence to combat Russia. According to John Schindler, a former analyst at the U.S. National Security Agency and a professor at the Naval War College, Estonia has few peers in the West when it comes to fending off Russian intelligence breaches. “The Estonians have dealt with the Russians, and before them the Soviets, for so long, they intuitively understand Russian intelligence culture and how they operate,” Schindler told me. “We don’t.” 

It wasn’t always so. In 2008, Tallinn suffered a major embarrassment when Herman Simm, once the Estonian Defense Ministry’s top security official -- and someone therefore privy to NATO secrets -- was discovered to be a Russian mole. Simm had been recruited by the Soviet Union in 1985. Ten years later, he was either re-recruited or reactivated by the Russian

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