After deftly evading the grasp of law enforcement agencies for more than a decade, the world’s most notorious arms trafficker made a reckless mistake.

Viktor Bout risked venturing outside of Russia, the one place where his close ties to high-ranking government and military officials offered him tacit protection, the one place where he could feel safe from arrest and extradition.

On March 5, 2008, Bout flew from Moscow to Bangkok to meet with representatives of a Colombian guerilla group seeking to overthrow the country’s democratically elected government. Bout came to finalize a lucrative deal to deliver millions of dollars of military-grade weapons from Eastern European warehouses to jungle outposts in Colombia.

What Bout didn’t know when he checked into his five-star Bangkok hotel was that he had fallen for a trap. The two purported Colombian rebels sitting across the hotel conference room table from Bout the next afternoon were actually U.S. Drug Enforcement Agency operatives carrying out a sting operation.

When the undercover agents asked Bout for missiles that could shoot down American aircrafts and arms that could kill American forces, Bout agreed to supply those and allegedly explained, “We have the same enemy.” Only minutes later, Thai police stormed the room. Then Bout’s two contacts revealed themselves as U.S. operatives.

"For the U.S. government, it was a major victory,” Michael Braun, the DEA’s former chief of operations, told Yahoo Sports. “He was arguably the largest and most sophisticated arms trafficker on the globe when he was arrested. He was the guy who could deliver virtually anything with certainty to any bad actor all over the world."

Fourteen years after the sting operation that put Bout behind bars and his arms empire out of business, the U.S. once again may have to decide how badly it wants to keep him locked away. Bout, the so-called “Merchant of Death” and the inspiration for the 2005 Nicolas Cage film, “Lord of War,” appears to be Russia’s preferred target in a potential prisoner exchange for American basketball star Brittney Griner.

On May 13, Russia paraded Griner through a Moscow courtroom in handcuffs and extended her pre-trial detention by a month, a display that some experts interpreted as an attempt to increase the pressure within the U.S to make a deal. That same day, multiple state-owned Russian news outlets reported that Russia would be open to swapping Bout for Griner.

[UPDATE: Brittney Griner released from Russian prison 10 months after arrest]

While Griner’s loved ones have urged the Biden administration to do whatever it takes to bring the two-time Olympic gold medalist home, Russia’s seemingly lopsided asking price complicates negotiations. The U.S. alleges Bout smuggled military-grade weapons to rogue leaders and insurgent groups across Africa and beyond, elevating conflicts from machetes and one-shot rifles to grenade launchers and AK-47s. Russia alleges Griner flew into Moscow on Feb. 17 with vape cartridges containing hashish oil in her luggage.

Despite that apparent imbalance, some Americans say the U.S. should consider returning Bout to Russia in exchange for Griner and other wrongfully detained American prisoners. Among those is the federal judge who sentenced Bout to 25 years in prison but says she wishes she could have been more lenient.

“To me, it’s unfair that he’s been tarred with this ‘Merchant of Death’ nickname,” Shira Scheindlin told Yahoo Sports. “I don’t think he’s as bad as he has been made to look like.”

Who is Viktor Bout?

Exactly how bad is Viktor Bout? The answer varies depending on who you ask. Russian state media calls him a “businessman” and an “entrepreneur.” His former website says he’s a “born salesman with undying love for aviation.” A longtime DEA agent once described him as “one of the most dangerous men on the face of the earth.”

Born in the Soviet outpost of Tajikistan to Russian parents, Bout, 55, displayed an early gift for mastering languages. He reportedly is fluent in more than a half-dozen languages, including English, French, Portuguese, Russian and Uzbek.

Bout has acknowledged graduating from the prestigious Military Institute of Foreign Languages, then working in Africa in the late 1980s as a Soviet military translator. The military language school was known as a training ground for the Soviet foreign military intelligence directorate known as the GRU.

When the Soviet Union teetered and collapsed in 1991, Bout, then in his mid-20s, astutely saw opportunity amid the chaos. Piles of weapons and ammunition lay discarded in dusty warehouses. Military planes sat abandoned on Soviet runways because there was no money for maintenance or fuel, and no one was flying them.

Relying on his military and intelligence connections, Bout acquired several Antonov cargo planes known for their heavy airlift capacity and ability to land in treacherous terrain. Those became the starting point for a private fleet of more than 50 Soviet cargo planes and a network of air-freight companies that hauled goods to and from far-flung conflict zones.

Bout’s planes reportedly carried anything from fresh-cut flowers, to frozen food, to U.N. peacekeepers, but authorities say he raked in most of his profit delivering arms and ammunition from old Soviet stockpiles. At Bout’s peak, according to the U.S Department of Treasury, he had “the capacity to transport tanks, helicopters and weapons by the tons to virtually any point in the world.”

The ability to supply that sort of firepower rapidly and with pinpoint accuracy helped Bout build a client list that included some of the world’s most notorious leaders. He made $50 million supplying the Taliban with military equipment, according to the U.S. Department of Treasury. He also allegedly inflamed conflicts in Liberia, Congo, Rwanda, Sierra Leone and Sudan.

Angola was one country where Bout allegedly defied United Nations sanctions prohibiting arms trafficking and U.S. peace-making efforts. A former high-ranking U.S. State Department official told Yahoo Sports that in the mid-to-late 1990s, Bout sold Soviet-era arms to both sides of the Angolan Civil War — the Marxist government and the UNITA rebels seeking to overthrow it.

“He was undermining our efforts to create peace in Angola,” the former State Department source said. “He didn't care what side of the issue he was on. He was in it for profit.”

Bout consistently stayed one step ahead of international investigators by repeatedly registering and re-registering his planes in far-flung countries, enabling him to avoid inspections and oversight. It also helped that Bout’s alleged arms deals often fell into a legal gray area, making him difficult to arrest or prosecute.

In the final years of the Clinton administration, with parts of Africa ravaged by civil war, bloodshed and ethnic strife, the National Security Council authorized the surveillance of government and rebel leaders in war zones like Liberia, Sierra Leone and Congo. NSC officials eventually noticed that each conflict had one common thread: Bout was supplying the weapons.

The NSC’s efforts to apprehend Bout ultimately fell apart when it could neither find an American law to apply to him nor persuade an African ally to issue an arrest warrant. In a 2000 letter to NSC African Affairs Director Gayle Smith, a South African official explained, "It is not clear from the information provided whether [Bout] has committed an act that has been criminalized under South African law and which falls under the jurisdiction of South Africa."

At the same time as other branches of the U.S. government were trying to build a case against Bout, the Pentagon reportedly hired him as a valued contractor. Bout received millions of dollars to deliver goods and equipment to American troops in Iraq, according to Douglas Farah and Stephen Braun, co-authors of the 2007 book “Merchant of Death.”

In the early 2000s, the U.N. also investigated Bout and accused him of supplying arms throughout Africa. One U.N. report said Bout had “at least five passports” and “at least five aliases.” A subsequent U.N. report alleged that Bout provided weapons to Liberian warlord Charles Taylor’s abhorrent regime to “gain illicit access to diamonds.”

While the U.N. reports carried no legal weight, they shined a spotlight on the work Bout had long been doing in the shadows. In 2004, the U.S. Department of Treasury froze what assets of his it could. Arrest warrants, raids and unwanted media attention soon followed.

The mounting pressure uprooted Bout and his wife from their home in the United Arab Emirates and caused him to retreat to Moscow. The protection of the Russian government made him practically untouchable there … unless someone could lure him out.

The sting on Viktor Bout

In the summer of 2007, a counterterrorism adviser to President George W. Bush approached the DEA’s Michael Braun with an audacious question.

Juan Zarate had just seen agents from the DEA arrest Syrian arms trafficker Monzer al-Kassar via an elaborate overseas sting operation. Now Zarate wondered if Braun's special operations division could devise a similar scheme to take down Bout.

"Every other three-letter and four-letter agency has taken a shot at him," Braun remembers Zarate telling him. "Could you guys try to bring him to justice?"

Over the next few months, the DEA crafted its plan to have agents pose as members of the FARC, a violent Colombian rebel faction financed by drug trafficking and other criminal activity. The FARC was a shrewd choice because the U.S. had already classified it as a terrorist group and because the Colombian guerillas were thought to be in the market for the same weapons that Bout had previously supplied other groups.

In November 2007, the DEA initiated Operation Relentless with the help of an informant who was friendly with Bout and associate Andrew Smulian. At the request of the DEA, the informant emailed Smulian and revealed he had a potential deal for Bout. After gauging Bout's interest, Smulian replied to the informant, “It may be that he can get his hands on items which you require."

The sting operation culminated in March 2008 when the DEA successfully baited Bout into leaving his Russian safe haven and flying to Bangkok to finalize the deal. DEA agents chose Bangkok because they had a good relationship with the Thai police and because they felt Bout wouldn't be suspicious traveling to a city so many time zones removed from the U.S. or Western Europe.

After Bout's meeting with undercover operatives ended with him shoved up against a wall with his hands in the air, DEA regional director Tom Pasquarello entered the hotel conference room. What struck the agent was how calm Bout was even with his life in flames and a dozen guns pointed at him.

"Do you have anything to say?" Pasquarello asked Bout.

"The game’s over," the arms trafficker coolly responded.

Bout may have accepted his fate then, but his fighting spirit resurfaced when the U.S. sought to extradite him. Portraying himself as a pawn in an American plot, Bout testified in a Thai criminal court that he ran a legitimate air cargo business and that he had traveled to Bangkok to relax and to try to make a deal to sell cargo planes.

Either eager to protect a citizen arrested abroad or wary of what intelligence secrets Bout might spill if he were extradited, Russia also tried to intervene on his behalf. Not only did the Kremlin publicly denounce the charges against Bout, American officials also became aware of underhanded Russian attempts to block his extradition to the U.S., to bribe key witnesses or to buy his freedom.

"Putin and other high-level government officials really tried to move heaven and earth and get him repatriated to Russia," Braun said.

Added Pasquarello: "Everything was on the table to try to free him. I'm telling you, you can't even imagine."

After a two-and-a-half-year legal tug of war, Thailand finally agreed to hand over Bout to the U.S. To Pasquarello, that meant a few anxious days of making sure Russia neither broke Bout out of his maximum-security Thai prison nor arranged for him to "meet a mysterious death."

On the day that Bout was scheduled to depart Thailand, the DEA still took no chances. A decoy motorcade of police vehicles left the prison and headed to one Bangkok airport. Minutes later, a second convoy drove to a different airport, this time with Bout part of the trip.

When Bout's flight landed at Westchester County Airport in New York, two DEA agents escorted him off the plane. For the first time, the Merchant of Death was on American soil.

Viktor Bout for Brittney Griner?

Viktor Bout’s most unexpected American ally turned out to be the federal judge who presided over his case.

For years, Scheindlin has publicly questioned if Bout is as villainous as his menacing nickname and cartoonish reputation suggest.

After a federal jury convicted Bout of all four charges, including conspiracy to kill Americans, Scheindlin rejected the government’s request that she sentence him to life in prison. Scheindlin instead gave Bout the minimum possible sentence of 25 years and called it “fundamentally unfair to this defendant” that she didn’t have the option to be even more lenient.

When reached by phone by Yahoo Sports last week, Scheindlin said her stance hasn’t changed. Echoing her arguments from Bout’s 2012 sentencing hearing, Scheindlin pointed out that Bout hadn’t committed a crime chargeable in an American court prior to his arrest and that there is no reason to believe he would have had the DEA not targeted him with its sting operation.

“I think the sentence was too long, but I had no flexibility,” Scheindlin said. “My hands were tied.”

Since his 2012 conviction, Bout has been at the top of the Kremlin’s prisoner exchange wish list. Russia has repeatedly signaled its willingness to do a potential swap for jailed Americans, but so far the U.S. has been unwilling to part with Bout.

Experts who spoke to Yahoo Sports agreed that securing Bout’s release is a priority for Russia because of his high-level government and military intelligence connections. They said that Bout operated with state protection throughout his arms trafficking career and that he often served the government’s foreign policy interests once Vladimir Putin rose to power and reconsolidated Russia’s fractured intelligence services.

To Farah, co-author of the definitive book on Bout, Russia’s efforts to get Bout back are to reward him for supplying its allies with weapons, for staying loyal after his arrest and for never agreeing to serve as a turncoat source.

To Stephen J. Blank, a senior fellow at the Foreign Policy Research Institute in Philadelphia, Russia’s interest in Bout is driven by fear of the secrets he could expose if coerced into telling U.S. authorities about Russia’s clandestine arms business.

“This is a guy who knows an awful lot about Russian gun-running operations,” Blank said. “He sat at the center of a whole network of Russian arms deals that all trace back to Putin. Once you understand that, you understand why they’re trying so hard to get him back.”

Since a prisoner exchange is Bout’s only potential path back to Russia for the next 11 years, his New York attorney says he had “one directive” when he took over as lead counsel. Steve Zissou openly admits he is trying to “change the narrative” about Bout, to “get away from ‘Merchant of Death’ or ‘notorious arms dealer’” and make a trade more palatable to the American public and the U.S. government.

To spruce up Bout’s reputation, Zissou promptly returns calls from reporters, leaves comments under articles he finds one-sided and writes letters to the editor that frequently go unpublished. Zissou’s message is simple: That Bout “wasn’t committing any crimes that were prosecutable in a U.S. court” until the DEA targeted him.

“He was retired and living in Moscow, minding his own business,” Zissou said. “He had never been to the U.S. before. He had never expressed any ill will toward the U.S. And then the U.S. government spent millions of dollars creating a fictitious crime that didn’t exist.”

One factor working in Bout’s favor is the amount of time that has passed since his 2008 arrest. After 14 years, it would be very difficult for Bout to reintegrate himself in an industry that shifts as rapidly as the arms trade.

“You have to know the actors and the terrain and you have to have access,” Farah said. “He’d have none of that now. As bad a guy as I think he is, I don’t think there would be anything lost sending him back now in terms of strategic value.”

The bigger obstacle for a prisoner exchange remains the optics. Could the U.S. stomach trading a notorious arms trafficker for a WNBA player allegedly caught carrying vape cartridges with marijuana oil? What about if the trade was for Griner and former Marine Paul Whelan, who is serving a 16-year sentence for espionage charges that the U.S. says are bogus?

Scheindlin, the federal judge who sentenced Bout, says she doesn’t believe “there would be any great injustice getting rid of this guy and letting him go back where he’s from in exchange for American citizens we really want back.”

“Now given the lack of equivalence between him and Brittney, I do think it would be more equal if the Russians are willing to release two Americans,” Scheindlin said.

Pasquarello, the former DEA agent who helped take down Bout, doesn’t see it the same way. He argued that it’s the government’s responsibility to find another way to bring Griner and Whelan home that doesn’t encourage Russia and other rogue states to keep seizing Americans as trade bait.

“You look into Viktor’s background and how many deaths are attached to his actions, and you want to trade this person?” Pasquarello said. “I don’t think there’s anyone involved in foreign policy and diplomacy who would describe that as a successful strategy. All that does is give governments incentive to hold high-value Americans in the future.”