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Rob Dobi for BuzzFeed News

TALLINN, Estonia — Russia is recruiting smugglers on its western frontier to work as spies and informants in an attempt to destabilize its neighbor Estonia, a gateway to the European Union and NATO, a BuzzFeed News investigation can reveal.

At least five men have been arrested in the last two years and convicted of spying on behalf of Russia. Their cases reveal how the Russian secret service, the FSB, operates across the border into a country that has a long and complicated history with its eastern neighbor.

Each of the five men was a known smuggler, of anything from people to cigarettes, and the FSB was able to force them to work undercover in exchange for avoiding lengthy sentences in Russian prisons. Once they had been recruited, they were tasked with passing on information about everything from Estonian military bases to details about patrols run by guards manning the border.

“They are an easy target for FSB recruiters,” Aleksander Toots, the deputy head of the Estonian Internal Security Service, known by its acronym, KAPO, told BuzzFeed News. Toots, who oversees KAPO’s counterintelligence arm and who has been personally involved in the investigation of all five men, said that it was virtually impossible to say no to the recruiters. “If you choose to decline, you might get into trouble because the FSB knows that you are a smuggler and are crossing the border illegally. The threat of ending up in a prison in Russia isn’t appealing. On the other hand, if you accept, you could hope for protection from the FSB in your criminal activity.”

The Russian tactic of turning petty criminals into spies on the ground mirrors a key feature of Russia’s cyber tactics: blackmailing criminal hackers into doing the government’s bidding. It is the latest illustration of a style of Russian intelligence operations that has caught the United States and its allies flat-footed, one that draws no clear line between traditional espionage, open criminality, and ambiguous business transactions.

Estonia, a small country of just 1.3 million people, has been grappling with its neighbor for decades. In 2007, it suffered a wave of debilitating cyberattacks suspected of having been carried out by Russia to protest Estonian plans to move a Soviet-era monument. Starting the following year, through 2013, Estonia arrested a host of high-level officials who had been spying for Russia, including two KAPO officers and the head of the country’s National Security Authority, Herman Simm. Now, in a tactic revealed in detail for the first time here, Russia is seeking lower-level spies to spy on its neighbor. The revelation will likely feed concerns of Russian meddling in Estonia, which already grew in the wake of Russia’s seizure of Crimea from Ukraine in 2014, marking a new stage in Russia’s approach to what it still considers its backyard.

Until recently, Estonia operated under the belief that it had US backing in the face of Russian aggression. In the wake of Crimea, then-president Barack Obama traveled to the capital, Tallinn, to assure the Baltic countries that the US, and NATO, was on their side. “You lost your independence once before. With NATO, you will never lose it again, he said. Now, with Obama gone and replaced by a president under investigation for his suspected ties to Russia and marred by ambiguous statements about his commitment to collective defense, the landscape has changed.

Now Russia is testing new methods — at first close to home, and then, inevitably, further abroad. As the world focuses on Russia’s capabilities in the realm of cyberattacks and misinformation campaigns, is it missing Russia’s ability to develop new methods of good old-fashioned on-the-ground spying?

The men convicted of spying on Estonia for Russia.

Estonian Internal Security Service

The five men convicted of spying for Russia don’t know each other, but they have much in common.

Of the five, four lived in the Russian city of Pskov, near the border with Estonia, and have both Russian and Estonian citizenship. Just one, who lived in Estonia, lacked Estonian citizenship, one of hundreds of thousands of Russian speakers whose families moved to the country when it was part of the Soviet Union, and who were rendered stateless when the country regained independence in 1991.

“I am certain that it isn’t only buying off one or two Russian border guards. The links must go much higher.”

All five men signed a written agreement of cooperation with the FSB and got cash for the tasks they carried out, according to Toots. The payment may have been as little as 2,000 rubles, or $ 35. But they didn’t do it for the money. The choice these men faced was simple: either go to prison in Russia or remain free and boost their criminal career with the knowledge that Russian border guards would turn a blind eye to their smuggling and they would also get some extra money from the FSB.

The effort appears highly organized, according to people involved in the investigations. Three different investigators from two institutions — the Police and Border Guard Board and the Tax and Custom Board, which investigates smuggling — told BuzzFeed News that they hadn’t seen any effort from the Russian side to stop and catch smugglers along the border for years now. “I am certain that it isn’t only buying off one or two Russian border guards. The links must go much higher,” one of the sources said.

There is also little, if any, risk at all for the FSB when hiring the smugglers. In Estonia they are known as prügikala, or “trash-fish” — they are disposable, too small to matter. If any of them is discovered, the FSB doesn’t lose a valuable asset that they spent years training, as they do with officers who work their way up through the system. And they can always hire a replacement. There are dozens of smuggling gangs operating along the 80-mile border between Estonia and Russia, and the 130-mile border between Russia and Latvia, another Baltic neighbor.

Pavel Romanov

Courtesy Estonia’s Tax and Customs Board

Pavel Romanov, 44, was one of the five men caught spying for Russia.

It was 1:15 p.m. on an unusually hot Friday in the late spring of 2014 when he decided to pull his car over near a team of border guards patrolling a crossroad near the border.

“I had held a party for fellow villagers last night. After a breakfast and shower I felt sober. I only wanted to double-check if I was ok to drive,” Romanov told BuzzFeed News, reiterating what he had told investigators about why he pulled over. To this day, Romanov isn’t quite sure why he pulled over, and he kicks himself for it.

Romanov was visibly drunk when he stepped out of the car, according to the statements of the four border patrol officers who saw him. And the border guards recognized him immediately. They had long suspected Romanov of being a smuggler. It was a badly kept secret in the area, but aside from some minor crimes — including a breach of public order and a case of illegal border crossing, for which he was fined, and failure to pay child support, for which he was sentenced to six months in prison — they hadn’t been able to prove anything. Now they could at least charge him with another crime. His breathalyzer test showed a criminally high level of alcohol.

Romanov was an experienced smuggler — his main business was smuggling tobacco, and he was very good at it. He led a gang of 10 people and gave each of them a specific task. His right-hand man, a smuggler named Vladimir, was responsible for buying the cigarettes in Russia and arranging transport to the border. Three other men, including Romanov’s 19-year-old son, Mihhail, stood guard to detect approaching border guards. There were drivers to take the contraband away and others who were positioned a couple of miles ahead to provide intelligence. Romanov himself commissioned the buyers in Estonia.

“Little did they know, however, that drinking and smuggling were the least of Romanov’s secrets. He had been a spy working for the FSB for 20 years. “

Romanov was known to treat everyone fairly. He and everyone else on his team earned 500 euros apiece for each operation, which consisted of two different trips over the border carrying 20 cigarettes cases — 400,000 cigarettes — into Estonia. In a part of the country where unemployment is soaring and the average monthly wage is as low as 800 euros, that was good money.

The border guards were happy to have nabbed him. Little did they know, however, that drinking and smuggling were the least of Romanov’s secrets. He had been a spy working for the FSB for 20 years.

Romanov was recruited by the FSB while working in Russia back in 1994, around the time Russia’s war in Chechnya was about to break out, Toots told BuzzFeed News. In an interview with BuzzFeed, Romanov said he was buying used Western cars from Germany and Finland at the time and selling them in Chechnya, a mainly Muslim republic that would fight two separatist wars in the wake of the Soviet Union’s collapse. At the time, Russians needed help with local knowledge. Romanov boasted of being close friends with the Chechen rebel leader Dzhokhar Dudayev at the time (though BuzzFeed News could not independently verify this), saying he knew the general well through the general’s daughter Dana — Dudayev had served in the Soviet military in Estonia in the the late ’80s and early ’90s. Now Dudayev was fighting on the other side, with the Chechens against Russia.

When war broke out in Chechnya, Romanov returned to Estonia — but continued working for the FSB. He carried out tasks for the FSB as well as for FSB’s border intelligence unit, according to Toots. He gathered information about Estonian border guard tactics, their patrol times, and locations of surveillance cameras, Toots said.

He was also tasked with gathering information about military and security structures in southeastern Estonia, like the Sänna warehouse of the Estonian Defence League, which is similar to the US National Guard, and the Kuperjanov Infantry Battalion base near the town of Võru. He also provided the FSB with information about officials in the various Estonian security agencies like the police, the border guards, and KAPO — including their habits, interests, and weaknesses.

Romanov's house on the border of Estonia and Russia.

Courtesy Estonia’s Tax and Customs Board

The border guards didn’t arrest Romanov for drunk driving that spring day, though he was forced to give them a statement. But they did, nearly a year later, decide to go after his smuggling operation.

By early 2015, investigators finally felt confident they had enough evidence to bust the gang. It would require an elaborate operation that included tax and customs officers assigned to KAPO.

The team chose the night of February 10, 2015, to make its move. Romanov’s gang was preparing for another smuggling run across the border. The temperature had dropped as low as 14 degrees Fahrenheit, the ground was covered in snow, and a bone-chilling wind was blowing. Someone stood watch at Romanov’s house, which was off the only road to the border. Closer to the border, the rest of the smuggling team was prepping in rented sheds.

Finally, the team of officers made its move, surprising Romanov and his cohorts when they were on their snowmobiles, driving multiple tracks through the snow to make it harder for anyone to trace where they were really going.

Investigators were surprised by what they found. When they were caught, the investigators found they were carrying a sophisticated cache of surveillance and smuggling equipment, from camouflage suits and masks to specially built rope harnesses to make it easier to move the heavy cigarette cases, night vision goggles, thermal cameras, radio jammers, and cameras that had been set up on trees to warn them when the border patrol was approaching. One night vision device was a military one, with its registration numbers scraped away. “You can’t buy things like that anywhere in Estonia,” one investigator said.

The team arrested Romanov immediately, and he quickly admitted to running smuggling operations.

Investigators proved that Romanov’s group had crossed the border illegally 13 times, smuggling more than 2.5 million cheap untaxed cigarettes and earning 80,000 euros (around $ 95,000). A customs officer involved in the investigation said that Romanov was ecstatic — the officer said he “clapped with joy” — when he realized what investigators would argue as the real size of his business had, in fact, been much larger.

As the court case got underway, Romanov decided to take a plea deal. On May 26, he was convicted of smuggling and sentenced to five years in prison.

The next month, KAPO sent a letter to the judge asking permission to interrogate Romanov in another criminal investigation. It’s unclear exactly when KAPO realized that Romanov was more than he seemed, since spying investigations are considered state secrets in Estonia. But they began to interrogate him about his connections to the FSB.

On October 22, 2015, he found himself in court again — convicted of spying and sentenced to four years and 10 months in prison. The sentence was reduced to 22 months in prison, but Romanov had to agree to pay regular visits to a probation officer.

Romanov was the most prolific of the five men who have been convicted of spying for Russia in the past two years.

Another, Aleksandr Rudnev, had barely turned 21 when he was arrested in March 2015. The FSB had also tasked him with gathering information about military exercises and the movement of Estonian army vehicles, according to information released by KAPO.

And then there is the case of Eston Kohver.

Two days after Obama gave his speech in Tallinn, Russian special forces kidnapped Kohver, a KAPO officer who was on duty on the border. The sting operation took only a couple of minutes. The Russians lobbed smoke grenades and flashbangs to disorient Kohver. The FSB then dragged him over the border to Russia, according to Estonian officials. Russia denies to this day that he was captured on Estonian soil.

Kohver was held in detention at Moscow’s notorious Lefortovo Prison and charged with espionage. Despite diplomatic pressure from the European Union and the United States, he was sentenced to 15 years in prison. Only a year later, on September 26, 2015, was Kohver able to return to Estonia after a classic prisoner exchange held on a bridge at the Estonia-Russia border.

“The FSB didn’t use Gruzdev anymore after the Kohver operation. His job was done.”

BuzzFeed News can now reveal that the man who lured Kohver into a trap on the border was a small-time smuggler named Maksim Gruzdev, according to Toots. Kohver was carrying a Taurus service pistol, as well as 5,000 euros in cash and a recording device, when he was kidnapped. According to Toots, Gruzdev had promised to put Kohver in touch with a third person who could provide information on cross-border corruption. The cash was for that third person.

KAPO knew it was Gruzdev who had laid out the trap for Kohver, but couldn’t go after him until the officer was safely back on Estonian soil. What’s more, the FSB didn’t use Gruzdev anymore after the Kohver operation. His job was done.

“He didn’t think that we knew about his role in the case and we managed to take use of it,” Toots said.

Officials from KAPO caught Gruzdev handing someone a petty bribe in the small town of Põlva in August 2015. But Kohver was still in prison in Russia, so investigators decided to wait to arrest him. They couldn’t risk hurting behind-the-scenes diplomatic negotiations to swap him for Aleksei Dressen, a KAPO officer who had been found guilty of treason for working with the FSB.

The long-awaited prisoner exchange finally took place on September 26, 2015. Kohver was swapped for Aleksei Dressen, who had been imprisoned in Estonia in 2012 on charges of spying for Moscow. A week later, on Friday, KAPO investigators arrested Maksim Gruzdev. Out of the five spies, he is the only one still serving time in prison. He is scheduled to be released this fall. BuzzFeed News sent a request to interview Gruzdev in prison, but Gruzdev didn’t reply.

The border of Estonia and Russia

Courtesy Estonia’s Tax and Customs Board

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