Paul Whelan has been imprisoned in Russia for nearly a year.Dimitar Dilkoff / AFP / Getty / The Atlantic

Elizabeth Whelan, a soft-spoken portrait artist from Martha’s Vineyard, has never considered herself political. And yet seated before this shrine of sorts—the Trump bobblehead next to the Trump-branded bottle of rosé; the Trump coffee mug; the Make America Great Again hats in red, white, and blue; the Trump tube socks; the SAVE FREEDOM: TRUMP/PENCE bumper sticker—she knows she is in the right place.

She is here, in this office, to talk about her brother, because she is only ever in Washington, D.C., to talk about her brother. On December 28, 2018, Paul Whelan was traveling from his home state of Michigan to Moscow for a friend’s wedding when he was arrested by Russian intelligence officers on charges of espionage. The 49-year-old, formerly a security chief for a manufacturing company, has been in a czarist-era prison in Moscow ever since. According to his family, his health is deteriorating, he has no access to English-speaking legal counsel, and his visits from American embassy officials are limited. And 57-year-old Elizabeth, who before Paul’s arrest spent her days painting and enjoying the Vineyard’s salt-stung air, has been thrust into the miasma of U.S.-Russia relations in a singularly personal way.

Which is how, on a recent Friday, she found herself in the office of David Urban, the Trump campaign official–cum–corporate lobbyist who speaks regularly with the president and counts his fellow West Point graduate Secretary of State Mike Pompeo as a close friend. That Urban, who led the campaign’s successful 2016 operation in Pennsylvania, took the meeting was a victory in itself. For months, Elizabeth has trekked back and forth to plead her brother’s case to the White House, Congress, the State Department—anyone who will listen. She’s made some inroads on Capitol Hill, where last month the House passed a resolution calling on Russia to present “credible evidence” against Paul, or release him from prison. But overall, she’s found high- and low-ranking officials alike to be skittish on the topic. “I would say we have a Russia problem, in the sense that a lot of people don’t want to engage with any subject matter that has the word Russia involved in it,” Elizabeth told me after her meeting with Urban, which I’d sat in on. “I might as well be taking a fainting couch and smelling salts around with me.”

Admittedly, there is never a good time for an American citizen to be detained in Russia. But given the Trump administration’s complicated, unpredictable, and often deferential relationship with the Kremlin, Elizabeth struggles to imagine a worse one. Earlier this summer, Paul used a brief court appearance in Moscow to beg for President Donald Trump’s assistance in his case. “Tweet your intentions,” he pleaded from inside a glass cage. Yet the president has stayed silent. (The White House did not respond to requests for comment on this story.)

For Urban, who met the Whelan family through a mutual contact, the decision to help Elizabeth, and to do so pro bono, was a no-brainer. “This is a humanitarian issue—an American citizen being detained,” Urban told me. “It’s completely separate from politics.” But of course it isn’t, as nothing ever is. Politics is why Elizabeth was meeting Urban that Friday. It’s why the bobblehead, the rosé, the socks, rather than unsettle Elizabeth, made the room glint with promise. As both she and Urban knew, settling into their chairs that morning for their first face-to-face, the way to attain Paul’s release was to make Donald Trump care.

“So,” Urban said, nodding toward her. “Let’s start from the beginning.”

Paul Whelan arrived in Moscow on December 22, 2018. His friend, a fellow American and former marine, was getting married there to a Russian woman, and had invited Paul as a tour guide of sorts for the wedding’s U.S. guests. Paul’s love for Russia was well known: In his work over the years in IT and security for international consultancies and manufacturers, he’d traveled to the country multiple times. According to The New York Times, he was also active on Vkontakte, Russia’s version of Facebook. He’d formed online friendships on the site with dozens of Russians, many of whom were retired military officers, and talked with them about his interest in the Russian language and culture.

According to Elizabeth, when Paul didn’t show at the wedding, his friend knew immediately to worry, and alerted the American embassy of Paul’s disappearance. For three days, Elizabeth said, her family was in the dark. “We didn’t know if he was dead or if he’d been captured by gangsters, or what was going on.” They searched for answers online, Googling phrases like “dead American in Russia.”

On New Year’s Eve, they found a news article that included a statement from the FSB, Russia’s federal security service and the successor to the KGB, confirming that authorities had arrested Whelan on suspicion of espionage. A Russian news agency, quoting an anonymous intelligence source, claimed that Whelan had been apprehended in a room at the Metropol Hotel—the site of his friend’s wedding—five minutes after a Russian citizen handed him a USB drive containing classified information. He was hauled into solitary confinement at Lefortovo, Moscow’s infamous Soviet-era prison used by the KGB for political prisoners.

Dan Hoffman, a former CIA official who ran the agency’s operations in Moscow, told me there is “zero” chance that Whelan is a spy. “There’s no evidence to indicate that he was doing anything wrong at all,” he said. “He’s not the only one who’s been arrested on false accusations—of course Russians do that to their own citizens all the time.”

Upon learning of Paul’s arrest, his family was just “relieved to know he wasn’t dead,” Elizabeth said. “But then we were faced with the uncertain task of ‘What do we do?’ Because nobody steps forward to help you.”

And this baffled Elizabeth, for the obvious reason: An American citizen was being held by a foreign government—one hostile to the United States—on charges for which that government refused to produce evidence. Where was her country’s outrage?

The obstacles to her brother’s release, as Elizabeth would soon discover, were twofold. No. 1: Paul Whelan was not a perfect victim. “His case is one of those that doesn’t come across as super clear-cut,” a senior congressional official and Russia policy expert, who requested anonymity in order to be candid, told me. “He’s not this Boy Scout on a goodwill mission to Russia who gets kidnapped.”

Paul enlisted in the Marine Corps in 1994 and was a staff sergeant in the Iraq War from 2003 to 2008. But in January 2008, he received a court-martial conviction on charges “related to larceny,” according to his service records. He was accused of attempting to steal $10,000 from the government while serving in Iraq, and using false credentials on a government computer system to grade his own rank-advancement courses. He ultimately received a bad-conduct discharge.

No. 2: the lingering question of whether this guy actually was a spy. At the time of his arrest, Paul was the global head of security for an international automotive-parts manufacturer. He is a citizen of four different countries—the U.S., the U.K., Ireland, and Canada—and keeps up-to-date passports for each. It didn’t matter that immediately following Paul’s arrest, current and former CIA officers batted down suggestions he was working for them, telling reporters that Paul’s court-martial likely would’ve barred him from ever joining the agency, and that the U.S. was unlikely to send an agent abroad without diplomatic cover. Nor did it matter that the Whelans adamantly denied the accusation, or that just days after Paul’s arrest, his FSB-appointed lawyer seemed to suggest to a reporter that Russians had long been monitoring Paul’s activity and saw him as a potential exchange for Russians currently jailed in the U.S.

“There was all this hesitation in political circles on the Hill” around the “spy question,” says Ryan Fahee, a former prosecutor for the Justice Department’s counterespionage division who represents the Whelan family pro bono. The few lawmakers who would take Elizabeth’s calls, he told me, would press her on “ridiculous questions” about Paul’s background. Ten months later, “I’m still getting those questions.” (Indeed, not five minutes into his face-to-face meeting with Elizabeth, Urban asks: “So … your brother is not a spy, right?”)

This is where the limits of a sister’s advocacy reveal themselves most plainly. The questions that run through Elizabeth’s mind in these moments go something like this: How do you explain that your brother is more than his shoddy military record? That tons of people have multiple citizenships, that you yourself have three, and No disrespect, Congressman, but do I seem like a spy? How do you make someone know the brother you know, and how do you cope when you realize you can’t?

“It’s very difficult for somebody like me, you know, the older sister—my younger brother in this situation. How does a person even start? A regular person suddenly blindsided by having their brother put in a Russian jail,” Elizabeth told me. “When I come to D.C., I try to keep a positive mental attitude, I try to be upbeat about what I’m doing. I tell myself it’s business that I’m here to perform.

“But sometimes it overwhelms me.”

Threatening any progress toward Paul’s release is the radioactive dynamic between Trump’s America and Vladimir Putin’s Russia—an obstacle, potentially, that not even a kidnapped Boy Scout could overcome. Many former intelligence officers have speculated that Paul’s detainment was retaliation for the U.S. arrest of Maria Butina, the 30-year-old Russian national who in November 2018 pleaded guilty to conspiring to act as an unregistered foreign agent. But Butina was released last month. Meanwhile, a Russian judge has extended Paul’s pretrial detention another two months.

“This whole circus with Russia from the beginning of this administration, including now with Ukraine, is absolutely not helpful,” the senior congressional official told me. “It’s made it much harder to do serious policy and get serious results with a country like Russia. It causes career officials and others to say, ‘I’ve got enough problems. I don’t want to be out there exposed on this, on anything I don’t have to be.’”

So in early 2019, when Jon Huntsman, the U.S. ambassador to Russia at the time of Paul’s arrest, appeared willing to take the lead on the case, White House officials and others at the State Department seemed all too happy to cede responsibility. By most accounts of those I spoke with for this story, Huntsman was deeply invested in securing Paul’s release, visiting him three times at Lefortovo. According to the senior congressional official, Huntsman’s involvement “provided a level of comfort for hesitant politicians,” such as the Michigan congressional delegation, who were vocal advocates of the House resolution condemning Paul’s detainment. The source said that Huntsman had succeeded in “displaying a high level of concern about Whelan to the Russian government without inflaming any tensions in the public realm.”

Still, even some of those who acknowledge Huntsman’s investment argue his advocacy was a failure. Most crucial, they said, the U.S. has yet to officially declare Paul wrongfully detained. That declaration would allow the government to assign his case to what’s called the FBI’s Hostage Recovery Fusion Cell, which pools resources across agencies to secure the release of Americans kidnapped or taken hostage abroad. Whether Huntsman sought such a declaration is unclear—he did not respond to my requests for an interview. But as Bill Browder, the prominent Kremlin critic, put it to me, “The State Department’s goal is to never elevate crises or have confrontations or bring things to a head … when in reality, the best way to deal with these situations is to scream bloody murder until they let him out.

“This is not a sensitive hostage negotiation—he’s been in jail for 10 months,” added Browder, the architect of the Magnitsky Act, which imposed sanctions on many top Russian officials. (Browder himself has been a target of bogus charges from Russia and was briefly detained just last year.)

The U.S. no longer has an ambassador to Russia: Huntsman resigned from his post in early August. And Trump, in nominating Deputy Secretary of State John Sullivan to replace Huntsman, has added yet another layer of complication to Paul’s case. Sullivan is a central figure in the House’s ongoing impeachment inquiry, given his proximity to Pompeo and others involved in Trump’s alleged quid pro quo with Ukraine.

In other words, beyond lower-level embassy staff, the U.S. government currently has no presence in Moscow. If officials had any incentive before to involve themselves in the U.S.-Russia morass—working under the reputational cover of Huntsman, perhaps—then they certainly don’t now. Which means, in Browder’s view, Paul’s release is now up to one person: It’s “just a question of Trump making the call.”

David Urban is supposed to be the guy who can make that happen. This is his purported value: his status as the advocate best positioned——through his relationships, his indispensability to Trump’s reelection efforts—to make a big ask of the president. Whether Urban will, at least in the near future, is another matter.

For the Whelan family, any fears that Urban had inflated his clout seemed to be quelled during that first meeting in his office a few weeks ago. There was the Trump paraphenalia—the tangible evidence of Urban’s allegiance to the president. Then, as they made their way outside to an Uber, bound for more meetings at the State Department and then at the White House, they crossed paths with John Gizzi, a reporter for the pro-Trump outlet Newsmax. “Dave! You going in as chief of staff?” Gizzi asked, referring to recent rumors of White House acting Chief of Staff Mick Mulvaney’s ouster. “Ah, not gonna happen,” Urban responded, laughing. “But if I do, you’ll be the first to know.”

Urban, a fast-talking Pittsburgh native who ends most declarative statements with “right?”—Paul was in Russia, right? Now he’s being held, and we don’t know why, right?—can claim most of his Trumpworld connections from college. His West Point class, apart from Pompeo, includes Mark Esper, the acting defense secretary, and Ulrich Brechbuhl, the counselor of the State Department.

Urban’s first goal, he told me, is to have Paul declared wrongfully detained. In the past two weeks, he’s held meetings to that end with officials at the State Department, the Defense Department, and the National Security Council. Some of these officials are the same ones to whom Elizabeth appealed on her own, without success. Elizabeth told me that when she met with John Sullivan—“a very nice fellow”—a few weeks ago, she was struck by someone so senior “giving me suggestions for what I should do. I come to Washington looking for someone to help me, and I get told how to help myself.” (Asked for comment on that conversation, and on Paul’s case more broadly, a State Department spokesman said in a statement: “We will continue to make the Russian government aware how much importance we place on the fair and equitable treatment of our citizens abroad, including Paul Whelan … We have repeatedly raised our concerns regarding the lack of evidence that has been presented in Mr. Whelan’s case.”)

“It’s a little easier for me to come in from the top,” Urban told me. He said he felt his first round of “high-level meetings” at the State Department “sent a good message that this is a priority,” and officials are now “helping me chart a course.”

As to why the wrongful-detainment declaration wasn’t managed under Huntsman’s leadership, Urban told me, “I don’t know … Maybe it was part of his strategy. I just don’t know the reasoning behind it.” He’s careful not to cast doubt on Huntsman’s efforts, praising him for “putting a great deal of personal energy” into Paul’s case. But he admitted that the current vacuum of U.S. leadership in Moscow has meant that attention to Paul has “taken a little dip.” (The State Department spokesman did not directly address my question about whether Pompeo intends to declare Paul wrongfully detained in the near future.)

Throughout our interview, three days after his meeting with Elizabeth, Urban frequently invoked the importance of a grand strategy to bring Paul home—comparing the task ahead to conducting an orchestra, or playing 3-D chess, or landing a plane just so. It’s “very delicate,” he said, acknowledging, this being his first time taking on a case like Paul’s, that “diplomacy is done a little bit slower than I care to do at times.” The next day, Urban would join President Trump on Air Force One en route to a speech in Pittsburgh. But he told me he didn’t plan to bring up Paul’s case. “I think it’s all about timing,” he said. “I have no compunction about talking to the president about it; it’s just—I want to make sure it’s all teed up correctly.”

According to the senior congressional official, raising the issue with Trump too abruptly, with conversations still unsettled at the agency level, is “not a ridiculous thing to be concerned about.” But others feel that the time for delicacy has long since passed. “Trump could easily make the call right now,” Browder told me. Whether a call from Trump would be enough to bring Paul home is less certain, but in Browder’s view, it’s the only viable option left. “At this point, I think it requires the Whelan family going on Fox News and telling their story so he can hear it himself. Because the normal channels of briefing won’t work.”

At the very least, the former U.S. ambassador to Russia Michael McFaul told me, “I am amazed that Trump has never once mentioned the wrongful detention of Paul Whelan.”

Still, Elizabeth told me she feels confident with Urban at the helm. “A lot of my effort has been just trying to understand who we should talk to,” she said. Officials that Urban has spoken to in the past few days alone “are people who I have barely known existed. It would’ve taken me months to get that sort of access.”

She told me that in the weeks since Urban agreed to help, she has felt, for the first time in months, “relief.” Her trips to Washington, she said, could often make her feel small. She described herself as “one small person from an island in Massachusetts trying to take on not only the Russian government, but the U.S. government.” But her eyes brighten when she begins telling me about the last time she saw Paul, about the July weekend he flew all the way from Michigan to help her set up her art show, because Paul was always doing nice things like that. She is telling me about what families owe one another. She is telling me, without saying so, that she no longer feels small.

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