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Where most people saw chaos, Viktor Bout saw opportunity.

Bout, a 55-year-old Russian, was the world's most notorious arms dealer before a U.S. court convicted him in 2011 and sent him to a prison in Illinois. He's now the focus of a potential prisoner swap between the U.S. and Russia, which holds two Americans the Biden administration hopes to free.

Bout was in his mid-20s when the Soviet Union fractured in 1991, leaving vast quantities of Soviet military hardware scattered across 15 newly minted countries. Most all of them were ill-equipped to pay their troops or keep track of the weapons they'd just inherited. Almost anything was available for a price.

Trained by the Soviet military as a linguist, Bout began acquiring Soviet military transport planes and loaded them up with weapons. The U.S. says he sold them all over the world — though primarily in Africa, the Middle East and Asia.

He was entrepreneurial, not ideological, selling to governments that were fighting rebels, and to rebels who were fighting governments. Separating fact from fiction has often been difficult when documenting Bout's work, but many reports said he even sold arms to both sides in the same conflict.

Bout always denied he was selling weapons, claiming he was flying flowers and frozen chickens to some of the world's most violent places.

He was always hard to pin down, but he lived openly in Moscow, traveled widely, occasionally spoke to reporters and seemed to welcome at least some of the attention. He became so notorious that Hollywood made a 2005 movie loosely based on his life, called the 

Despite facing international sanctions and threats of arrest, Bout managed to stay a step ahead of law enforcement until 2008, when he was captured in a sting operation in Thailand, organized by the U.S. Drug Enforcement Agency.

The Thais extradited Bout to the U.S. two years later, where he was charged with conspiring to kill Americans. He was convicted in a Manhattan court in 2011, and is a little less than halfway through his 25-year sentence at a prison in Marion, Ill.

So why would Russian leader Vladimir Putin want to bring Bout back?

After all, he made his money selling weapons that had been intended for use by the Soviet Union's military and successor countries.

When CIA director William Burns was asked this question last week at the Aspen Security Forum, he said succinctly: "That's a good question, because Viktor Bout's a creep."

Dan Hoffman, a former CIA officer who served in Russia, said Putin's motives should be viewed through the lens of his ongoing battle with the U.S.

"Every opportunity he gets, Vladimir Putin wants to show that he can go toe-to-toe with Russia's main enemy," Hoffman said. "It's a real good public relations move for him to show that he's taking care of his own."

The U.S. and Russia have a history of working out deals to gain the return of their own citizens. In April, the U.S. released a Russian pilot convicted or conspiring to bring drugs into the U.S., and Russia freed 

, a former Marine who'd been convicted of assaulting a Moscow police officer.

More commonly, the countries kicked out suspected spies in tit-for-tat deals.

But the current negotiations appear uneven in some respects. The U.S. would be freeing a convicted arms smuggler who operated on an international scale for close to two decades.

Meanwhile, Secretary of State Antony Blinken said Wednesday that the two Americans, 

 have been "wrongfully detained and must be allowed to come home."

Griner, 31, is the pro basketball star who has pleaded guilty to having hashish oil in her suitcase at a Moscow airport in February. Whelan, 52, a former Marine who traveled openly to Russia for years, was arrested in 2019 and convicted on espionage charges in a secret trial.

Dan Hoffman says he supports the efforts to win the release of the Americans.

"These are dirty deals, but there's two bad options," he said. "One is letting American citizens get sick, and potentially even worse, in jail. And the other one is make essentially a dirty deal. If it's me, I'll get my U.S. citizens out."

Blinken said he's presented a plan to Russia for the return of two Americans, though he did not mention Bout by name. Blinken plans to speak with his Russian counterpart, Sergey Lavrov, though it's not clear when that might be. The two have not spoken since Russia invaded Ukraine in February.

A U.S.-Russian prisoner swap would signal the two countries can still do business on some level despite the terrible state of relations and the backdrop of the war in Ukraine, where the Americans are the leading arms supplier to the Ukrainians.

But analysts say there's no real prospect that the overall atmosphere — which has been going from bad to worse — is likely to improve.

Greg Myre is an NPR national security correspondent. Follow him 

Crime, Law and Justice

Greg Myre

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Bout is a Russian who was the world's most notorious arms dealer in the 1990s and early 2000s. He's serving a 25-year prison sentence in Illinois, but could be freed as part of a U.S.-Russia swap.

Who is Viktor Bout, the prisoner the U.S. may trade for Brittany Griner?

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