Estonia on the front lines of Russian spies

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“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 intelligence service SVR -- the successor to the KGB. Simm was caught owing only to the sloppy tradecraft of his second and final case officer, Sergei Yakovlev. Posing as Antonio Graf, a Brazilian-born businessman, Yakovlev made promiscuous approaches to other would-be recruits, including a senior Lithuanian official, which prompted Vilnius’ counterintelligence agency to start the initial investigation that exposed Yakovlev and then Simm.

Simm is now in the fifth year of a 13-year prison term, but much about his case remains a mystery. (It seems he was also in the employ of Germany’s intelligence services for some time after rejoining the Russians.) The damage he wrought, however, was obvious. In his book Deception: Spies, Lies and How Russia Dupes the West, Edward Lucas, the only journalist to have interviewed Simm in prison, writes that this breach, the worst in NATO’s history, “unveiled the alliance’s innermost secrets, from the content of meetings to the details of its most important codes.” Apparently, Simm provided Russian officials “accounts of the arguments that raged inside the alliance about Russia, about the relative strength and weaknesses of different countries, and psychological assessments of its senior officials.” Even worse, perhaps, than the intelligence, Simm’s exposure made established member states fear that the newer NATO members -- especially those from the Soviet Union -- were liabilities rather than assets.

Estonia, which joined NATO in 2004, took keen notice of those anxieties. Over the past five years, Tallinn has concentrated on proving -- to itself and to its NATO allies -- that it is able to defend itself against Russia (using overt and covert means). It has also made a strong case for why confrontation with Moscow is unavoidable.
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There is more.

Estonia was once part of the Soviet Union so it has some knowledge of Russia tradecraft for spying and it also has people familiar with the Russian strategy and tactics as well as the equipment used by the Russian army.   The US has done training exercises in Estonia to prep the people for a potential insurgency should the Russians try to overrun Estonia.  The country has a tech sector that is also profitable.