Sipher told The Washington Post that Russia has “an incredibly robust and talented counterintelligence service” and that the United States is well aware of the sophistication of Russian espionage. “The way we run spy cases in Moscow is very, very carefully, very meticulous,” Sipher said. “We don’t send in random Americans without diplomatic immunity to collect low-level stuff.”

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Whelan’s job title alone would probably attract attention, not avoid it. “You wouldn’t use a cover like a global security guy to commit espionage,” Chris Costa, a former U.S. intelligence officer who is the executive director of the International Spy Museum in Washington, said to The Post.

The U.S. ambassador to Russia, Jon Huntsman, visited Whelan on Wednesday, five days after he was detained. U.S. Secretary of State Mike Pompeo, speaking to reporters in Brazil, said that once the administration has more information about Whelan’s case, if it determines that “the detention is not appropriate, we will demand his immediate return.”

The case clearly differs from that of Ryan C. Fogle, an American diplomat who was detained in Russia in 2013, Sipher said. In that instance, Fogle was ordered to leave the country after the Russian government accused him of working for the CIA and trying to recruit a Russian agent to spy for the United States.

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Russia said Fogle was caught with wigs, sunglasses, a compass and a small knife, among other items. He was also carrying $130,000 in cash and a letter that offered up to $1 million a year for providing consistent information. It was written in Russian.

A better comparison, Sipher said, would be the 1986 arrest of American journalist Nicholas Daniloff. Daniloff was detained in Moscow shortly after U.S. officials arrested Soviet physicist Gennadi Zakharov in New York and charged him with espionage. Daniloff was eventually sent back to the United States in a prisoner swap that also freed Zakharov.

Similarly, Whelan’s arrest came shortly after Maria Butina, a Russian gun rights activist, pleaded guilty to conspiring to infiltrate conservative U.S. circles. The timing has sparked suspicions that Russia may have detained Whelan to negotiate another swap.

A person familiar with Whelan’s case said that with Daniloff, “the Soviets wanted to trade a low-value asset for a high-value asset, and it would not surprise me if we’re looking at a similar sort of situation here."

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Earlier this week, Whelan’s twin brother, David, told The Post that “it is inconceivable to me that he would have done anything to break the law in Russia.”

Paul Whelan has visited Russia multiple times in recent years, his family and acquaintances said. Several Russian acquaintances contacted by The Post described Whelan as a fun-loving man with a genuine interest in Russia. He had a basic command of the language, which he picked up through language-learning websites, they said.

Whelan has an account on VKontakte, Russia’s answer to Facebook, that dates to Nov. 10, 2010. VKontakte is almost exclusively used in the Russian-speaking world. Considering that Whelan is not known to have worked or lived in Russia, having a VKontakte account is somewhat unusual.

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His account has more than 60 Russian friends, and his status updates and messages over the past nine years range from whimsical musings about life to political sentiments. In one post, he called President Barack Obama a “moron”; in another, written near the time of President Trump’s inauguration, he wrote “GOD SAVE PRESIDENT TRUMP” and included American flag emoji. Whelan also called for Edward Snowden, who leaked classified information from the National Security Agency, to be sent to a “GULAG.”

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According to one acquaintance who met him online a decade ago, Whelan liked to chat about his time as a Marine and his family in Michigan. “I don’t think Paul is working as a spy or anything like that. He just wants to travel,” said the friend, a resident of the Russian city of Nizhny Novgorod.

Costa cautioned that it’s hard to speculate what Whelan may have said or done that could have flagged him as a potential threat to Russian authorities. “Anytime any American travels abroad, they can say something that could be construed as insensitive or violating security, or make some kind of commentary, and that can always be used as a pretext for arresting someone,” he said.

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“Is it possible this guy is doing something that was mildly illegal that they can define as spying?” Sipher said. “Perhaps, but the one thing Putin knows as a professional intelligence officer is that he knows what real spying looks like, he knows what the U.S. does, and he knows very well that this is not part of it.”

O’Grady reported from Washington. Ferris-Rotman reported from Moscow.