FOR SOMEONE SO POLITICALLY connected in so many places, Bout's personal history, all the little pieces that make up the man, has remained the stuff of urban legend. He is variously described as having been born in the Soviet republics of Tajikistan, Turkmenistan, or Ukraine. He is married and has a daughter who lives in Spain, as well as a brother named Sergei in Moscow, also believed to be active in the arms-smuggling business. He is known to hold as many as five passports in various aliases and speaks at least six languages, including Russian, Uzbek, Portuguese, French, English, and perhaps several African dialects. As a young man, his language talents were developed at the Soviet Military Institute of Foreign Languages in Moscow, a primary recruiting vehicle for the GRU, the Soviet military intelligence service. Whether Bout became a GRU officer remains unknown (there is speculation he joined the KGB), but his post-Soviet career bears a striking similarity to one of the GRU's primary Cold War tasks: the provision of weapons to communist movements around the world. Bout, for his part, was unimpressed by Marxist politics, but the basic mechanics of moving large quantities of military equipment to remote locations he might easily have mastered while in the GRU's employ.
After the Soviet Union's implosion, Bout went into business for himself, using his connections to gain access to mountains of former Warsaw Pact weapons and ammunition and buying up the old military cargo aircraft required to move them. There were plenty of paying customers to be served, and in the years that followed, Bout served them all, often working for both sides of a conflict to double his profit. He armed the Taliban and the Northern Alliance in Afghanistan, the Revolutionary United Front in Sierra Leone, Charles Taylor's regime in Liberia, UNITA in Angola, various Congolese factions, and Abu Sayyaf, a militant Islamic group in the Philippines. As recently as 2006, says Farah, the arms dealer was believed to be making shipments to the Islamic Courts Union in Somalia and Hezbollah in Lebanon, among many others.
Despite his success on the black market, Bout escaped notice for many years. "For a long time, nobody cared," says Winer. "He had a decade-long period before there was a real understanding of what he was doing, and then we lacked the tools because it was all cross-border." For Bout, the walls began to close in only in March 2001, when the UN included his name on a "travel ban" list for his dealings with Charles Taylor's Liberia. In subsequent years, the Belgian government issued an Interpol "red notice" for his arrest, and the U.S. government, through the Treasury Department's Office of Foreign Assets Control (OFAC), incrementally tightened economic sanctions against Bout, ultimately placing him on its list of "Specially Designated Nationals," freezing the assets of any companies or individuals found to have dealings with him.
Prior to Bout's arrival in Thailand, there had been several failed attempts to apprehend him. In February 2002, British and Belgian police got word that the arms dealer was scheduled to fly into Athens, Greece, but Bout was tipped off at the last minute. Authorities picked up his trail again in March 2004, having learned that Bout planned to attend his daughter's birthday party in Spain, but the Madrid train bombings caused him to cancel the trip. "Sometimes he's been lucky," says Galeotti. "Sometimes he's been wily and thought, 'Hang on, this doesn't quite pan out right.' Other times it may well be that he was tipped off. He's got contacts in all sorts of places. The story is that he managed to get away with it for as long as he did."
IT REMAINS UNCLEAR WHEN the DEA's investigation of Bout began, but "it mushroomed and went operational in November," says Sanders, the DEA spokesman. By that time, the agency was running a paid informant (confidential source 1, or "CS-1," in the federal indictment), who was an old acquaintance of Bout associate Andrew Smulian—a contact the DEA would exploit to penetrate Bout's inner circle. Little is known about Smulian, aside from that he is a British citizen who once served as an advisor to one of Bout's airlines and had risen to become one of the arms dealer's trusted lieutenants. At the DEA's request, CS-1 emailed Smulian, explaining that he had a business proposition for Bout and requesting that Smulian meet him on the Dutch Caribbean island of Curaçao, a resort haven better known for scuba diving than arms dealing, where he would introduce his old friend to the prospective buyers. Smulian agreed but, making clear the financial and legal strains his boss was feeling, suggested taking precautions against surveillance. "Our man has been made persona non-G—for the world through the UN," he wrote back. "All assets cash and kind frozen, total value is around 6 Bn USD, and of course no ability to journey anywhere other than home territories. Listed on US black list.... All access and communications monitored, and therefore we should not make use of any form of contact, and all existing and past comms are electronically interogated [sic], and copied. My new phone is OK, since I never call him on that."
The meeting took place just after New Year's in a Curaçao hotel room. CS-1 introduced Smulian to two men, "CS-2" and "CS-3", both undercover DEA informants, who passed themselves off as representatives of the FARC. CS-2 played a lower-level FARC operative, while CS-3 adopted the title of "El Commandante," indicating his supposed high rank within the organization. Together, they explained their desire to acquire large quantities of heavy weapons, including surface-to-air missiles. In demonstration of their "good faith," they provided Smulian with $5,000 for his time and travel expenses, as well as a new cell phone, which they assured him was safe for his use. It was not, of course, and immediately investigators began monitoring Smulian's communications.
In the days that followed, Smulian used his DEA-monitored phone to call another, apparently higher-ranking member of Bout's network, named in the federal indictment as coconspirator 1 ("CC-1"). Smulian explained that he needed to visit Bout in Moscow to discuss some business and requested assistance assembling the necessary visas and travel documents. CC-1 happily complied, even suggesting some of the city's better hotels. After checking in with Bout, CC-1 emailed Smulian, conveying their boss' request to "confirm the list" of weapons before leaving for Moscow. Smulian replied that the desired shipment was well within Bout's means. "Standard ground equipment," he wrote. "Must be good stuff...no rubbish."
DEA surveillance records based on remotely conducted phone and Internet traces indicate that Smulian met with Bout in Moscow on Monday, January 21. There, the arms dealer displayed a series of photographs of the FARC's senior leadership and asked Smulian to identity the buyers from the pictures. According to Sanders, the informants were not members of the FARC and therefore did not appear in Bout's photo file, a detail that perhaps should have caused him to think twice before moving ahead with the deal. How Smulian responded to Bout's effort at due diligence is among the questions left unanswered by the federal indictment. "Maybe he convinced Bout that he was dealing with a lower level group than would have been in the pictures," Farah speculates. Certainly, there was a financial incentive for Smulian to get his boss to accept the Colombians as clients. "I think Smulian wanted this thing to go through" and may have "lied to Bout about who they were," says Sanders. Whatever happened, Bout was convinced enough to proceed, even extending an offer to launder money for the FARC (at 40 percent interest) and assuring Smulian that "any communists are our friends." He instructed Smulian to arrange a meeting with CS-1, the informant posing as the lower-ranking FARC operative, and another unknown member of Bout's network to go over the details of the purchase. Ever concerned with security, Bout directed Smulian before leaving Moscow to ditch his cell phones, SIM cards, receipts, and any other evidence that would "indicate where he had been and with whom he had been meeting," according to Bout's indictment.
From Moscow, Smulian proceeded to Copenhagen, Denmark, where CS-1, his old friend and original hookup on the deal, and the junior FARC operative were waiting. He relayed to them an offer from Bout. The Russian had "100 pieces" (surface-to-air missiles) available for sale, which he said could be "air dropped with great accuracy." In return, Bout's operation would accept payment, presumably in cash, to be picked up at a remote Colombian airstrip. Allowing for time to consider the proposal, the men agreed to meet again in a few days in Bucharest, Romania, to continue the negotiations.
By now, with the deal nearing its conclusion, all three DEA informants insisted on a meeting with Bout before finalizing the transaction. Bout, it seems, was also intrigued to meet his new clients. Bucharest was selected for this purpose, as it was a country to which he had traveled safely in the past. Still, Smulian was protective of his boss and urged the Colombians to agree to the deal without meeting Bout, explaining that the Russian was "a very high profile figure and risked arrest if he traveled to Romania," according to the federal indictment. When the Colombians refused, Smulian called Bout directly and handed the phone to "El Commandante," the senior FARC commander. The two men discussed possible meeting locations, considering Cuba, Nicaragua, and Armenia, but could not reach an agreement, probably out of the informant's concern that local enforcement in those countries might not cooperate with DEA's plans to arrest Bout.