Bout assured Ricardo and his pal, Carlos, both working for the Colombian Marxist rebel insurgency known as FARC, that he shared their hatred for the United States. “We have the same enemy.”

It could have been the start of a beautiful friendship.

The guerrillas and Bout talked for two full hours, first in the mezzanine lounge of the Bangkok Sofitel, then holed up in a bland conference room on the 27th floor. No lunch, no wine, none of the orchid-draped prostitutes who draw sex tourists to Thailand. Just water, tea and business, business, business.

The Colombians described life in the jungle under constant fire from the government in Bogota and its American military advisors, with their powerful helicopter gunships ripping across the canopy.

Bout, a mustachioed, 41-year-old Russian already known as the Merchant of Death with a long bloody history in Congo, Rwanda, Sierra Leone and other war zones, offered sympathy, and relief, in the form of a massive arsenal.

He listed what was on offer: 30,000 AK-47 assault rifles, 10 million rounds of ammunition, or more, five tons of C-4 plastic explosives, ultralight airplanes outfitted with grenade launchers, mortars, unmanned aerial vehicles, Dragunov sniper rifles with night vision, vehicle-mounted anti-aircraft cannons that could take down an airliner, and, most audaciously, 700 to 800 shoulder-fired homing surface-to-air missiles — known in the West as SAMs or MANPADs, for man-portable air-defense systems.

That was a massive arsenal, enough to arm an army. But the SAMs were the big attraction, and Bout was offering many more than Ricardo and Carlos had originally requested — they’d asked for just 5,000 AK-47s and a mere ton of explosives. Bout was also volunteering some items, like the cannons, they hadn’t asked for at all.

Ricardo and Carlos weren’t newbies. Ricardo was a former Colombian soldier and weapons expert for right-wing death squads and their adversaries, Colombian cartels. Carlos, introducing himself to Bout as “the money guy,” was a doctor’s son who had turned his education to laundering drug money. They rocked back in their chairs as Bout scribbled the numbers on a notepad: “AA = 100 + 700-800.” That meant, 100 SAMs immediately, then another 700 to 800 in later shipments.

He encircled the notation with heavy lines. As Ricardo well knew, terrorist groups the world over would thrill to get their hands on even just one or two of those light, potent killing machines. A team of fighters firing one of these small guided projectiles could prevent helicopters carrying special operations troops from landing to mount an attack on a remote jungle stronghold.

Bout knew all that. He also knew that if FARC leaders chose, they could sell off some of their cache to other, crazier zealots like al Qaeda, to unleash chaos anywhere.

As an offensive weapon of terror, a SAM is breathtakingly effective. A tiny ragtag band could down a single passenger airliner, inflicting mass casualties, then claim that to have more missiles in position, near three or four major international airports. The threat could be a lie, but how would the authorities know? A few suicidal, homicidal people with a SAM could paralyze international travel and commerce. For that reason, in 2004, the U.S. Congress jacked up the penalty for selling SAMs to a mandatory minimum of 25 years in federal prison and a maximum of life behind bars.

Bout was undaunted. As he pitched weapons to the Colombians, he coolly jotted down numbers, doodled a little ultralight, scribbled and boxed the letters “UAV,” referring to an armed drone. Today, remote-controlled armed drones are commonplace in the Ukraine war, but they weren’t in 2008.

Bout offered the Colombians even more — instructors, advisers, technology. All this bounty, he said, for $20 million to $30 million, to start. That was a whopping transaction, by conventional underworld standards, but Bout knew that despite their battered clothes and dirty fingernails, the guerillas were good for the money. He hadn’t dealt extensively with the FARC — most of his clients were African strongmen — but he did some research about Latin America on his laptop the night before the meeting. FARC leaders, though vaguely Marxist and listed as terrorists by the U.S. State Department, were known to be ardent capitalists. In 2006, the U.S. Justice Department had filed an indictment against 50 FARC leaders, accusing the organization of producing half the world’s cocaine and sending $25 billion worth of cocaine to the United States and other countries. Colombian National Police teams, often joined by agents of the U.S. Drug Enforcement Administration and U.S. Army special forces soldiers, regularly flew surveillance missions and mounted occasional lab raids — which is why the guerillas wanted anti-aircraft batteries.

Ricardo and Carlos admitted that they had so much money they didn’t know what to do with it, especially in Europe, where cocaine was increasingly popular. “We can produce around 40 million euro in every month,” Carlos said. He asked for advice on how to launder the cascade of cash, which was becoming cumbersome.

“Truth?” Bout replied. “We can find you the way to, to, uh, do it properly.” He recommended certain Russian banks.

After about two hours of fruitful business discussions, the Colombians excused themselves, allegedly to call the man who had kindly provided them the introduction to Bout. But actually, the call was routed to Robert Zachariasiewicz, an agent with the U.S. Drug Enforcement Administration, who had opened a criminal investigation into Bout in June 2007. He was with other DEA agents and a team of Thai policemen, in a room a few floors below. DEA had arrested Ricardo and Carlos years earlier, flipped them into cooperating insiders and trained them for undercover missions. For this job, the agents had outfitted the pair with tiny audiovisual devices that had recorded the long conversation with Bout. “Zach,” as his partners called him, hadn’t been listening in on the conversations because the devices didn’t transmit; their cover would have been blown if Bout swept the room with an emissions detector. But when the operatives told the agent, “Hey, we got everything,” he knew what that meant.

As Zachariasiewicz confirmed when he and his partners quickly downloaded and checked the covert digital recordings, Bout had made a string of incriminating statements that violated specific sections of U.S. federal law. That meant he could be indicted in the Southern District of New York, which handled most federal terrorism cases. The eventual charges — conspiring to kill Americans, to kill American officials in the performance of their duties, to support terrorists and to sell anti-aircraft missiles — carried a minimum of 25 years in prison and a maximum of life.

Bout’s repeated, earnest references to killing American helicopter pilots were crucial, because prosecutors in New York could use them to defeat his potential defenses, that he was entrapped, that he was just blustering, that he was simply scamming the Colombians. On the tape, he sounded deadly serious. In the following days, the agents would find much more evidence on his laptop and in his bag to prove that he knew the arms industry well and that he intended to carry out the arms supply drops he described to Ricardo and Carlos. Importantly, he had a map that pointed out U.S. radar installations in Colombia, so he could instruct the pilots of his cargo planes to avoid them.

The team had a quick group call with prosecutors at the Southern District. “We knew we had him eight ways to Sunday,” Zachariasiewicz recalled this week in an interview. “We had every confidence that if we got him to the Southern District, we had him dead to rights.”

But first, Bout had to be arrested. The Thai cops burst into the conference room door, followed by Zachariasiewicz and other DEA agents. Bout’s business partner, Andrew Smulian, was arrested as well, and the agents play-acted a fake arrest of Ricardo and Carlos. It probably didn’t fool Bout for long. The budding bromance with the Colombians was done.

It took four years and one month, but Bout was extradited to the United States, convicted and sentenced to 25 years in prison. And then last week, the United States let him go, swapping him to secure the release of Brittney Griner, a WNBA star arrested and jailed in Russia for possession of a small amount of cannabis.

Even President Joe Biden has acknowledged that the swap wasn’t exactly fair, that at best Griner was an inadvertent criminal and Bout an experienced, lethal one. But in the days since the swap, what has most troubled the DEA investigators who brought Bout down is the consequences of his release going forward.

Several are convinced he’ll soon reemerge as a player, helping Russia sell and acquire weapons in violation of international sanctions imposed in response to its invasion of Ukraine and earlier human rights violations.

“The Merchant of Death is back in action, with more hatred against America and with greater motivation to fuel conflicts and support Russia in its outrageous and disastrous war with Ukraine,” says Derek Maltz, who as head of the DEA Special Operations Division oversaw the undercover investigation of Bout.

“Bout was a master,” says Mike Braun, DEA chief of operations at the time. “There was no one who came close to his ability to move any type of armaments around the world and deliver them with absolutely precision, with air drops, landing on unimproved air strips, using old Soviet heavy cargo aircraft.”

Zachariasiewicz says he’s worried about the signal the United States has sent by swapping him for Griner.

“I think American citizens everywhere just got made a commodity,” he told me last week. “We just told bad actors everywhere that it’s good business to falsely detain or kidnap American citizens, and the best bargaining chip you can have is an American citizen. We just told them we will negotiate, so you better have some equity in your back pocket.”

Braun disagrees with those who argue that Bout is a has-been, that his network has frayed and his business model collapsed. If anything, Braun says, Bout has probably made valuable contacts over the nearly dozen years he has spent in the U.S. prison system.

“Anyone who thinks he’s washed up and [Russian President Vladimir] Putin is not going to push him back into service, it’s beyond me,” Braun said. “People who believe that don’t understand how the real underworld works.”

The Bout case grew out of DEA’s mission, launched after the al Qaeda attacks of Sept. 11, 2001, and the U.S. invasions of Iraq and Afghanistan, to hunt down “narcoterrorists,” meaning, people who used drug profits to finance terrorism and war. The definition covered FARC, the Lebanese Hezbollah, Afghanistan’s Taliban, and numerous smaller actors and groups.

Zachariasiewicz initiated the DEA investigation of Bout in June 2007, based on information from the joint DEA-Colombian investigation that Chepe Boyaco, a notorious gunrunner and cocaine transporter for the FARC, was negotiating with Bout for large quantities of heavy military-grade weapons, including surface-to-air missiles.

Other influential people in Washington were interested in Bout, for entirely different reasons. In August 2007, Braun, Maltz and Lou Milione, an agent with Maltz’ Special Operations Division, went to the White House to brief Juan Zarate, President George W. Bush’s deputy national security adviser on Milione’s successful undercover operation against a Syrian terror financier. Zarate, a rising young star in the Bush firmament, listened for a while, then pulled out a news clip about Bout. “Here’s a guy you ought to take a crack at,” he said.

Zarate had been tracking Bout for some years. In 2004, when he was in charge of a U.S. Treasury unit that sanctioned bad actors, Zarate saw to it that Bout was blacklisted for supplying arms to Charles Taylor, a warlord whose rebel army in Liberia and Sierra Leone drugged and recruited children as soldiers, carried out atrocities and imprisoned women as sex slaves. (Taylor would eventually be convicted of war crimes and is currently imprisoned in the U.K.) At that time Bout’s air cargo fleet was known to be delivering weapons to strongmen in other African countries, including Angola, the Democratic Republic of the Congo, Liberia, Rwanda, Sierra Leone and Sudan. The Treasury investigation charged that Bout’s companies had moved $50 million in arms to the Taliban regime, prior to the U.S. invasion of Afghanistan a few years earlier. With the U.S. engaged in Afghanistan in a long and ultimately failed war with Taliban insurgents, any arms trafficker with contacts to the Islamic extremist movement was in Treasury’s crosshairs.

To Zarate’s frustration, Treasury sanctions didn’t faze Bout. Even the U.S. Department of Defense ignored them. In 2004, investigations by journalists from the L.A. Times found that some Pentagon contractors had hired Bout companies to move cargo into the Iraq war zone.

Maltz, whose brother, a U.S. Air Force special operations sergeant, had died in Afghanistan, took Zarate’s point. He sped back to the Special Operations Division, an unmarked building near Dulles International Airport, and summoned Zachariasiewicz. “You gotta get on this case,” he said.

Zachariasiewicz smiled. He’d opened an investigation two months earlier. He was already on it, but somehow, the boss hadn’t heard yet.

“I fucking love you, dude,” Maltz said.

Zachariasiewicz was good as his word. He moved the investigation with astonishing speed. Deep in central Africa, he and his partners located a British bush pilot named Mike Snow, who had once worked for Bout and fallen out with him and was more than willing to help end his career. Snow led the agents to Bout partner Andrew Smulian, a shady South African down on his luck. In January 2008, with the agents watching from behind tiki lights and bougainvillea, Snow and Smulian met at a beach club on the island of Curacao, Snow introduced Smulian to Carlos and Ricardo, onetime traffickers who were now on DEA’s payroll as undercover operatives. They proposed a multi-million-dollar arms deal. Smulian would get a big commission, but they had to meet personally with Bout.

Smulian flew to Moscow to put the proposition to Bout, who agreed to meet the “FARC reps” in Bucharest. To put Bout behind bars, the U.S. agents needed the meeting to take place in a country with an extradition treaty with the United States. Romania was one.

Zachariasiewicz, other DEA agents and the operatives spent three maddening weeks there waiting for Bout, who didn’t show. “It has gringo centers of operations, lots of big ones,” he told Smulian in a wiretapped call. He sensed that the Romanian capital was crawling with American spies. He was right. The CIA had a big station in Bucharest and a secret prison code-named Bright Light on the north side of Bucharest; Khalid Sheikh Mohammed, the mastermind of the 9/11 attacks, and other high-value terror suspects had spent time there.

Before long, Bout’s hunger for money and action got the better of him. He agreed to meet in Bangkok, which also had an extradition treaty with the U.S. When confronted with Thai police holding with handcuffs, with Zachariasiewicz, Milione and other DEA agents behind them, Bout didn’t try to talk his way out. He realized that he had talked too much already.

“You have all the cards,” he told the DEA agents.

But they didn’t have all the cards, and everybody knew it. Keeping Bout locked up in Thailand was a labor-intensive marathon.

In the back of the room at the Bangkok Sofitel stood the stage director of the three-continent take-down, Milione, Zachariasiewicz’s boss, head of an elite man-hunting unit within the DEA’s Special Operations Division. Milione had an unusual background: He’d been a professional actor who had studied at the fabled Circle in the Square theater school, acted under the direction of Joanne Woodward, got acting tips from Paul Newman, and played Will Smith’s lover in the film, Six Degrees of Separation.

Before and after Bout’s arrest, Milione became famous within DEA for organizing a string of successful lures of international bad guys, all without firing a shot, all meticulously designed to meet the requirements of U.S. courts and defendants’ rights. He never lost a case.

His superpower was an understanding of human psychology, possibly honed by his theater studies. Deception, he taught his agents, nearly always trumped force. For most career criminals, he played on their avarice.

Bout didn’t need the money from the Colombians, and he had been safe in Moscow. He was known to be tied to Russian intelligence services and the Kremlin, which protected his reign as undisputed king of the international arms trafficking underground.

Moscow’s support was evident when Bout’s extradition process got underway. A U.S. diplomatic cable, dated Feb. 13, 2009, and later released by Wikileaks, reported, “There have been disturbing indications that Bout’s ... Russian supporters have been using money and influence in an attempt to block extradition.”

“Following Bout’s arrest, the Russian government denounced the charges and summoned the Thai ambassador in Moscow,” Braun wrote in the Aug. 5 issue of Foreign Policy magazine. “It then covertly deployed money and influence in an attempt to scuttle his extradition to the United States.” The first Thai court that heard the case ruled against extradition. A higher court overruled it and extradited Bout to New York in November 2010. He was convicted on four counts in November 2011, and in April 2012, was sentenced to 25 years in prison. (To the frustration of the prosecutors and agents, federal Judge Shira Scheindlin rejected the prosecutors’ request for a life sentence, saying no arms had actually been delivered. This was true, but agents contended an actual shipment of lethal goods was too risky to attempt.)

It was Bout’s greed that seduced him to that fateful meeting at the Bangkok Sofitel. Like many super-rich underworld barons, he had an insatiable itch for more. Just more. Milione and his agents understood that peculiar psychology. So did Bout’s business rivals.

One of those was Paul LeRoux, a South African arms-and-drugs merchant based in Manila. LeRoux had one of those “All About Eve” moments when he heard of Bout’s arrest. He didn’t drink, so he popped the aluminum pull-tab of a Diet Coke, his beverage of choice, and celebrated with an aide, a European mercenary he called Jack.

“The guy should have known better and been more protective for his person,” LeRoux scoffed to Jack, who told me the story for my book on LeRoux. The Russian, LeRoux said, was past his prime — vain, sloppy and a publicity hound besides.

Once Bout landed in the bribe-resistant U.S. prison system — his latest lock-up, according to court records, was the federal prison in Marion, Ill., where he was U.S. Bureau of Prisons inmate 91641-054 — the Kremlin turned to seeking a swap. Various Americans ran afoul of Russians authorities in the years Bout was in U.S. custody, but none of his stature. With the arrest of Griner, a celebrity athlete with a devoted following, the Russian government finally had the leverage it sought.

Bout’s next move is far from certain, but widely feared all the same.

U.S. authorities do not know how much money he has stashed in Moscow and other bolt holes, but they believe he is highly motivated to strike back at the U.S. and support Russian Vladmir Putin’s Ukraine war.

Some Africa specialists fear that Putin will press him into service to advise Russian oligarch Yevgeny Prigozhin, and his mercenary force, the Wagner Group, which is playing a key role fighting on the ground in Ukraine and has been implicated in some of the worst war crimes attributed to Russian forces. Prigozhin and Bout are both believed to be linked to Russia’s military intelligence agency known as GRU, and may well have crossed paths in Africa where they were both working after the collapse of the Soviet Union.

Analysts say that even if Bout steers clear of the war in Ukraine, he can still do a lot of damage in Africa as the Wagner Group expands Russia’s presence, trading in timber, minerals and other natural resources.

“Wagner is Russia’s coercive tool in Africa,” says Joseph Siegle, head of research at the Africa Center for Strategic Studies at the National Defense University, an arm of the Pentagon.

“While the numbers that are deployed in Africa may seem small,” Siegle says, “in fact, they’re having very far-reaching political effects to keep regimes that are supportive of Moscow in power. This has wide-reaching geostrategic implications for Russia’s involvement in Africa. Wagner is helping prop up some of the more destabilizing forces on the continent. Russia’s engagement is making them even more unstable.”

“Africa is a great profit center for the Wagner Group,” says Tim Wittig, an American scholar based in South Africa, specializing in studying threat finance and wildlife trafficking. Wittig says that Bout’s logistical skills, contacts and discipline, far superior to those displayed by Wagner Group, “could really help solidify Wagner’s footprint in Africa and make it harder to dislodge.”

Tom O’Connor, a former senior FBI agent specializing in domestic terrorism, now a consultant, takes the view that Putin’s play is more likely aimed at stirring up political division inside the United States, in part by refusing to include a former Marine, Paul Whelan, in the swap for Griner.

“Taking Paul Whelan off the table is strategic on Putin’s part,” O’Connor wrote. “Reaction in many camps has been to attack the administration. ... Republican leaders, who have already said they are going to stop payments to assist Ukraine, are outwardly attacking Biden and making continued Ukraine support more difficult. Putin released Griner … to continue efforts to inflame the Right against the Left in the U.S. The end result, he hopes, is less support to Ukraine and to continue his efforts to divide U.S. population. Score one for Putin.”

If O’Connor is right, Putin has achieved a win-win. Biden had every reason to know there would be a domestic political firestorm over the release of Bout. Justice Department officials made their opposition to the swap and release of Bout well known, in internal debates and through retired former top officials like Braun, to the world.

“We’ll pay for this at some point,” Braun told me. In arresting Bout, he says, “DEA worked with six or seven other agencies, other countries and ministers of justice, heads of law enforcement agencies and a number of three-letter agencies in this town. The foreign counterparts cooperated with us because they knew how dangerous this guy was.”

Going forward, Braun said, the ability of our system to bring malign actors to justice may well be in doubt.

“They believed in our judicial system and believed they could never accomplish in their countries what we could – to get Bout locked behind bars,” he said. “The next time we have one of these situations, they’re going to be questioning what the real outcome could be, down the road.”