In March 2014, the U.S. government sanctioned Dmitry Rogozin—a hardline deputy to Vladimir Putin, the head of Russia’s defense industry and longtime opponent of American power—in retaliation for the invasion of Crimea and eastern Ukraine.

Eighteen months later, the National Rifle Association, Donald Trump’s most powerful outside ally during the 2016 election, sent a delegation to Moscow that met with him.

The meeting, which hasn’t been previously reported in the American press, is one strand in a web of connections between the Russian government and Team Trump: Attorney General Jeff Sessions and former National Security Adviser Michael Flynn both denied speaking with the Russian ambassador, which turned out to be untrue; former campaign manager Paul Manafort supported pro-Russian interests in Ukraine; Secretary of State Rex Tillerson won an “Order of Friendship” from Putin; and then, of course, there’s the hacking campaign that U.S. intelligence agencies say Russian launched to tilt the election in Trump’s favor.

Meeting with Rogozin, a target of U.S. sanctions, is not itself illegal—as long as the two sides did no business together—explained Boris Zilberman, an expert on Russian sanctions at the Foundation for Defense of Democracies. But, he noted, it is “frowned upon and raises questions… those targeted for sanctions have been engaged in conduct which is in direct opposition to U.S. national security interests.”

Which raises the question: Why was the NRA meeting with Putin’s deputy in the first place?

The NRA had previously objected to the parts of the U.S. sanctions regime that blocked Russian-made guns from import into the United States. But curiously, David Keene, the former NRA president and current board member who was on the Moscow trip, insisted the meeting with the high-ranking member of the Kremlin government had nothing whatsoever to do with geopolitics.

“Rogozin is chairman of the Russian Shooting Federation and his Board hosted a tour of Federation HQ for us while we were there,” Keene told The Daily Beast. “It was non-political. There were at least 30 in attendance and our interaction consisted of thanking him and his Board for the tour.”

Rogozin tweeted photos of the meetings, writing that they discussed a forthcoming rifle competition in Russia.

But Rogozin is no ordinary Russian official, and his title extends far beyond being merely the chairman of a shooting club. His portfolio as deputy prime minister of Russia includes the defense industry. One issue where Rogozin seems particularly interested is cyberwarfare, which he has heralded for its “first strike” capability. And he’s well-known in Russia for being a radical—often taking a harder line than Putin himself.

Rogozin was the leader of the ultra-right party called Rodina, or Motherland, and famously believes in the restoration of the Russian Empire, including what he calls “Russian America” (i.e., Alaska).

To wrestle control of the party, he turned its course from a party that was occasionally in opposition to Putin to a strictly pro-Putin party. In 2005 Rogozin and his party miscalculated Putin’s anti-immigrant mood and got kicked out of the parliament for a chauvinistic promotion video that said: “Let’s Clean the Garbage!” featuring Central Asian workers eating a watermelon and spitting on the ground.

Still, Rogozin stayed loyal to Putin and soon was appointed Russian ambassador to NATO at the time of the Russia-Georgia War—his main responsibility at the time was to prevent Ukraine and Georgia from joining NATO. Today his Motherland party is back in the parliament, trying to unite right-wing movements in Europe.

“It is disconcerting that they would be meeting [with a Russian official] about anything given their vocal support of the president,” said Rep. Mike Quigley, a member of the House Intelligence Committee, which is investigating Russia’s attempts to influence the 2016 presidential elections. “Due to the NRA’s opposition to sanctions, it defies credulity that they wouldn’t have discussed sanctions and their extraordinary support for Donald Trump’s campaign.”

“Russia is not America’s friend. And it’s stunning to hear that while they were attacking our democracy, one of the largest organizations supporting Trump was cozying up with a sanctioned Russian in Moscow,” said Rep. Eric Swalwell, who is the top Democrat on the House Intelligence Committee panel that oversees the CIA.

Rogozin’s inclusion in U.S. sanctions, prior to his meeting with the NRA delegation, marks him as an American adversary. But if that designation raised red flags to Keene and his compatriots—including board member Pete Brownell, top NRA donor Joe Gregory, and Trump supporter Sheriff David A. Clarke—they didn’t mention them, before or since.

The White House designated Rogozin for sanctions through an executive order in March 2014 after the Russian annexation of Crimea in Ukraine. Perhaps it’s only coincidence, then, that a few months later, the NRA’s Institute for Legislative Action protested when the Treasury Department banned the importation of Kalashnikov firearms under authority granted to them from that same executive order.

“These latest sanctions will no doubt engender the idea among some that the Treasury Department is using a geopolitical crisis as a convenient excuse to advance the president’s domestic anti-gun agenda,” the NRA-ILA wrote at the time.

The National Rifle Association’s support for Trump was unprecedented—and it seems to have paid off. The organization backed Trump in May 2016—much earlier than they had endorsed other candidates in previous election cycles, and before he had even been officially named the Republican presidential nominee.

The NRA spent $30.3 million to elect Trump—more than even the top Trump super PAC, which spent just $20.3 million, according to OpenSecrets.

This proved to be an important piece of the puzzle for the president’s eventual victory, giving him bona fides among Democrats from working class families.

“They got behind him early. It tends to be a lot of movement conservatives, a lot of Republicans —but the NRA’s membership is also so powerful in union households,” said Richard Feldman, a former NRA lobbyist who wrote a book, Ricochet, about his experiences. “Union leaderships are very concerned about what the NRA has to say… This year it was a very important. NRA was the first major group to get behind Trump.”

Indeed, there is a solid case to be made that the NRA’s endorsement and support was among the most important of any group this election cycle. The NRA lined up television advertising space early, when rates were lower, and had money to spend when the Access Hollywood scandal struck, reading with a fresh advertising spot to support Trump.

“There are many claimants to the honor of having nudged Donald Trump over the top in the presidential election,” wrote Fred Barnes, executive editor of the conservative magazine The Weekly Standard, last week. “But the folks with the best case are the National Rifle Association and the consultants who made their TV ads.”

Soon after the election, the Trump administration rescinded an order, issued in the waning days of the Obama administration, that banned lead ammunition in various hunting and fishing areas—the NRA immediately applauded the action.

In retrospect, the second week of December 2015 is notable: In Moscow’s Metropol Hotel, now-disgraced Trump national security adviser Gen. Michael Flynn dined with Putin at a dinner held by Russia Today, a state-sponsored propaganda outlet.

The NRA delegation’s 2015 trip to Russia took place the same week, lasting from Dec. 8-13, according to Clarke’s public financial disclosure forms, (PDF), and included not only the people who met with Rogozin but a number of other NRA dignitaries, including donors Dr. Arnold Goldshlager and Hilary Goldschlager, as well as Jim Liberatore, the CEO of the Outdoor Channel.

Various members had various stated reasons for going. At least one was there for business reasons.

“Mr. Liberatore traveled to Russia to discuss our new outdoor lifestyle service MyOutdoorTV (MOTV) and prospects for international distribution,” said Liberatore’s spokesman, Thomas Caraccioli. Liberatore did not meet with Rogozin, he added.

The delegates who were contacted by The Daily Beast did not respond to questions regarding how they paid for their trip. But Clarke, as the sheriff of Milwaukee County, Wisconsin, was required to fill out public disclosure forms outlining any private money he received for travel (PDF).

The trip was sponsored at least in part by the organization, The Right to Bear Arms, a firearms advocacy organization founded by Russian national Maria Butina, a former Siberian furniture store owner who now lives in Washington, D.C., and serves as a link between Russian political circles and the American capital’s conservative elite.

“A delegation of the world’s largest gun rights civic organization—the National Rifle Association of the US (the NRA) visited Moscow on an official trip and met with supporters of the Right to Bear Arms movement,” wrote Butina in Russian in December 2015, posting a photo of the delegation on her organization’s Facebook page.

Clarke reported that Butina’s organization paid $6,000 for his meals, hotel, transportation, and excursions during his time in Russia. Brownell, the CEO of a prominent firearms company and an NRA board member, paid for the remainder, including his airfare and visas.

It is unclear where Butina’s firearms advocacy organization gets her money—it is a puzzling group, considering that Russia does not have a large grassroots movement for gun rights like the United States does.

Butina does, however, have a close relationship with Alexander Torshin, the former deputy governor of Russia’s central bank who has been accused by Spanish authorities of laundering money for the Russian mob. Neither Butina and Torshin responded to requests for comment.

Both Torshin and Butina pride themselves on their close relationship with the National Rifle Assocation, bragging on social media about their life memberships in the organization and posting photos of themselves with Keene, a former president of the NRA.

They’re not the only ones who posted photos showing links with the NRA: Rogozin posted photos of his meetings with the NRA in 2015. In one photo, the deputy prime minister is standing at what appears to be a shooting range with Gregory, Brownell, and Keene.

In another photo, Rogozin is at a conference table with Clarke and Brownell. Putin ally and former Russian senator Alexander Torshin is also seated with the group, along with a number of other unidentified individuals.

A White House spokesman declined to comment, as did the NRA.

Whatever the NRA’s ultimate reason for sending a delegation to Moscow, the conservative movement in D.C. is starting to slowly shift their views on Russia and Putin.

In May 2014, Keene criticized President Obama for not doing enough to confront Putin.

“The United States under President Obama’s leadership is content to issue rhetorical denunciations, insult Mr. Putin by claiming he runs a second-rate country that doesn’t understand the times in which we live, and deny he and his friends visas to visit the United States [emphasis added],” Keene wrote in the Washington Times, where he is now an editor.

With Trump about to enter office, in January 2017, Keene was singing a different tune.

“We seem prepared to believe any evil of Vladimir Putin’s Russia, which has with its second-rate military establishment and failing economy somehow morphed in the minds of many Americans into a greater threat than the old Soviet Union [emphasis added],” he wrote.

Asked why the contradiction, Keene employed some Trumpian logic.

“The two statements aren’t inconsistent,” he told The Daily Beast.

—with additional reporting by Anna Nemtsova, Michael Weiss, and Katie Zavadski.