He has seven aliases, a handful of passports, and has been described by U.S. officials as one of the world's most prolific arms traffickers, with clients ranging from the Taliban to Liberian warlord Charles Taylor.
But today Viktor Bout sits in a cell in Thailand awaiting extradition to the United States to face criminal charges, including conspiracy to kill U.S. nationals and provide material support to terrorists, that could put him behind bars for life.
A 43-year-old former Soviet Air Force officer, Bout was the inspiration for the 2005 film "Lord of War" starring Nicholas Cage. He allegedly funneled weapons to conflict zones in South America, the Middle East, and Africa.
Douglas Farah, co-author of a 2007 book about Bout titled "The Merchant of Death" says Bout had an uncanny ability to move weapons to trouble spots that were inaccessible to most arms traffickers.
"As someone told me in the book, he was the ultimate mailman and you never shoot the mailman," Farah says. "There were very few other people who could deliver what he could deliver, across the African continent particularly, but also in Afghanistan, where you have no roads, no trains, no other method of transportation."
Bout says he runs a legitimate air-transport business and denies involvement in illicit activities. He has long evaded attempts by the United Nations to block his travel and financial activities.
"He was violating UN arms sanctions on different countries, but the punishment for that is for the UN to say, 'You're a bad person, please don't do it again,' and then you just keep on flying, which is what he did," Farah says. "So there was no specific law of any specific country that he had violated, which made it very difficult for the amorphous United Nations structure to ever do anything."Thailand Arrest
Bout was arrested in a luxury Bangkok hotel in March 2008 in an elaborate sting operation in which U.S. agents posed as arms buyers from the Revolutionary Armed Forces of Columbia (FARC).
A Thai appeals court ordered Bout's extradition last week, following more than a decade of attempts by U.S. and international law enforcement to bring him to justice.
Russia fiercely opposes Bout's extradition. Speaking to reporters in Yerevan on August 20, Russian Foreign Minister Sergei Lavrov suggested that the court's ruling was political.
"We regret what in my opinion is an unlawful, political decision that the appeals court in Thailand has made," Lavrov said. "According to the information available to us, this decision was made under very strong pressure from the outside. This is sad."
Bout's extradition was originally scheduled to take place on August 25, but Thai officials announced that would be delayed because all the necessary legal procedures had not been completed.Soviet Connections
The son of an accountant and an auto mechanic, Bout was born in the Soviet Union in Dushanbe, now the capital of Tajikistan. He has at times claimed to be from Ashgabat, Turkmenistan, and has also been identified as Ukrainian.
Bout studied at the Military Institute of Foreign Languages in Moscow and is said to speak six languages. After graduating, he became an officer in the Soviet Air Force and was initially posted to Angola, where he is alleged to have worked for the KGB.
Bout, however, denies any connection to the Soviet intelligence agency.
Whether or not the speculation about KGB ties is true, analysts say Bout appears to enjoy high-level connections among the Russian political elite.
"It is clear that he has a very high respect in Russia. How do you say it in Russian? He has a 'roof' in Russia [eds: protection from high officials]. And it is very high," Farah told RFE/RL's Russian Service recently.
Bout left the military in the early 1990s as the Soviet Union collapsed and began assembling a fleet of more than 50 cargo planes cast off by the government for a private shipping business.
'The Merchant Of Death'
In the ensuing years, the U.S. indictment alleges, Bout and his associates traveled the world and used a network of front companies to channel massive quantities of arms and ammunition from poorly-guarded Soviet arsenals to militants and despots in Africa, Asia, and South America.
According to Farah, Bout also transported attack helicopters, antiaircraft systems, and antitank-mine systems -- making it "highly unlikely" that Bout did not have at least tacit support from Russian intelligence.
The most well-documented case involving Bout concerns former Liberian President Charles Taylor, who is now on trial for war crimes for his involvement in Sierra Leone's vicious civil war of the 1990s.
In UN documents, Bout was identified as a "dealer and transporter of weapons and minerals [who] supported former President Taylor's regime in [an] effort to destabilize Sierra Leone and gain illicit access to diamonds."
Bout also allegedly armed both the Taliban and the Northern Alliance in Afghanistan, various Congolese factions, Libyan strongman Muammar Qaddafi, and both sides of Angola's civil war. He has also been accused in Western media reports of ferrying weapons to Al-Qaeda and of delivering Russian arms to Hizballah in Lebanon ahead of the 2006 war with Israel.
In an interview with Britain's Channel 4 News last year, Bout admitted that his planes brought weapons into Afghanistan in the mid-1990s, but said they were to supply the government and not the Taliban. He has vehemently denied any business dealings with Al-Qaeda and maintains he ran a legitimate cargo business.A Worldwide Brand
Indeed, Farah says at least part of his fortune, at one time estimated to be billions of dollars, was amassed by transporting everything from flowers to chicken on the flights back from weapons deliveries.
In perhaps the most ironic twist of Bout's career, his companies were hired by the United States and its contractors in the early 2000s to ship goods into Iraq.
Most of these flights, which according to Farah numbered into the hundreds, occurred after former President George W. Bush had issued an executive order making it illegal to do business with Bout, identifying him as a security threat to the United States. Farah says that even after the mistake was identified, the flights continued.
Bout's companies were reportedly used by the United Nations to transport peacekeepers to Somalia, French troops to Rwanda, humanitarian goods to post-tsunami Sri Lanka.
He also transported hostage negotiators to the Philippines, when in 2000, a group of tourists were being held by the militant organization Abu Sayyaf -- to whom Bout had allegedly supplied arms in the past. He was also a key arms supplier to the Bosnian Muslims during the 1992-95 war in Bosnia-Herzegovina, according to Farah.
After years of skirting officials and operating by proxy around the globe, Interpol issued a 2002 arrest warrant for Bout in connection with a money-laundering case. By that time, he had made his way back to Russia, where the government said there was no evidence to suggest he had committed illegal actions. It has maintained that position.
Analysts say that should Bout eventually be extradited, it would be a major victory for the United States, which would have the opportunity to glean valuable information about Russian intelligence and militant groups around the world.
Speaking to reporters in Bangkok on August 20, Bout's wife, Alla, accused the United States of leaning on the Thai authorities to extradite here husband.
"I believe that in this issue there's been tremendous pressure from the American side," she said. "The Americans have been quite open in letting the world know that they will exert pressure on the Thai side to get my husband extradited to the U.S."