Supremely intelligent and cunningly amoral, Bout was seen in Washington as the quintessential figure of international crime. Illustration by Stanley Chow

Viktor Bout made his first major foray into the weapons business in 1995, on a pleasant summer day in Bulgaria. A Russian entrepreneur who was then twenty-eight years old, he had flown to Sofia from Sharjah, the third-largest city in the United Arab Emirates, where he had lived for the previous two years. Sharjah was a kind of postmodern caravansary—as Bout told me recently, it was a place with “practically no law.” Although he had arrived in the Emirates not knowing much about Arab culture, he had a cosmopolitan ability to adapt to new circumstances. He was intending to enter the field of aviation. Supple with languages, he could flip among Russian, English, Portuguese, and Esperanto; today, he says, he can “read fifteen or sixteen languages, go to the market with nine or ten, and fluently speak five or six.” He started spending time at the cargo hangars at Sharjah’s international airport, got to know the pilots and crews, and soon formed an air-freight company, Air Cess, with a small fleet of Russian planes.

In Sofia, Bout checked into the Park Hotel Moskva, a shabby, state-owned high-rise, and set out for the office of a Bulgarian arms dealer named Peter Mirchev. Bout was comfortable doing business almost anywhere, be it an Eastern European city or an African jungle airstrip. Air Cess was doing particularly well in Africa, where he sometimes worked with despotic regimes. Bout’s pilots flew televisions, air-conditioners, and expensive furniture from Sharjah to ragged African capitals, and delivered planeloads of West African francs from Senegal to surrounding countries. Air Cess had also begun shipping textiles and electronics from Sharjah to Afghanistan, a country that was then led by President Burhanuddin Rabbani. Bout had grown close to Rabbani’s defense minister, Ahmed Shah Massoud, whom Bout described to me as “a real revolutionary,” adding, “You could see the flame in his eyes.” Massoud was concerned about the advance of Taliban rebels, and one day his deputy asked Bout if he could also hustle guns.

Bout, who had the brash confidence of the autodidact, didn’t have a source of weapons, but he knew that he could find one. A friend had recently given him the phone number of Mirchev, and Bout called him and introduced himself. As Mirchev recalls it, Bout faxed him a list of the Afghans’ requests.

After Mirchev read it, he told Bout, “Come to Sofia.”

Mirchev was just a few years older than Bout, but he was already an experienced arms broker. At the end of the Cold War, he had realized that Bulgaria’s weapons manufacturers, which had scant access to the global market, needed someone to “help them make connections to the world.” As Mirchev, whom I met recently in Sofia, told me, “Nobody spoke English. I did.” He had quickly become an important conduit for weapons exports.

Bout arrived at Mirchev’s office, and they went out for dinner. Bout had a sly smile, and his blue eyes were offset by a brown mustache; he wore a sports jacket with an open-necked shirt. Mirchev, a small man with boxy cheeks, liked him, but was struck by his illiteracy in the arms trade. “He didn’t know anything,” Mirchev told me. “He mistaked the calibres, he mistaked the systems, he mistaked the weapons.”

After dinner, Mirchev and Bout went for drinks at an outdoor café, on a cobblestoned street canopied with tram lines, and hashed out a business plan. Mirchev proposed that he would manage the supply side, while Bout would handle the transportation. Bout agreed. “Viktor is a fast learner and he is very easy with the contacts,” Mirchev told me. “He could reach the right people at any time.”

The Afghan weapons contracts were dauntingly large. “They were faced with war, they needed us badly,” Mirchev said. I asked him about the scale of the shipments. “How many tons?” he said. “I never calculated tons. I calculated money. It was huge.” And, for Bout, it was just the beginning: within five years, he would be known as the world’s preëminent arms trafficker.

From a young age, Bout, who grew up in the Soviet backwater of Dushanbe, Tajikistan, yearned to see the world. The son of an auto mechanic and a bookkeeper, he honed his English, in part, by listening to ABBA and Chicago records. As a teen-ager, he explored two common ways out: sports and the military. First, he travelled around the Soviet Union playing competitive volleyball. He eventually quit, he told me, to have more time for girls. At the age of eighteen, Bout was conscripted into the Soviet Army, and he spent two years with an infantry brigade in western Ukraine. When his term ended, he applied to the Military Institute of Foreign Languages, in Moscow. He was accepted, and studied Portuguese there.

Stephen Blank, an expert on the Soviet and Russian military at the Army War College, calls the institute a “breeding ground” for intelligence officers. Bout insists that he never was a spy, but Mirchev, a former C.I.A. officer, and a Ukrainian organized-crime figure all told me that Bout once worked for the Soviets’ foreign-military-intelligence directorate, or G.R.U.

In 1988, Bout left the institute and went to Mozambique, a former Portuguese colony, with a group of Soviet military advisers. One evening in Maputo, at a function at the Soviet Embassy, he began a conversation with a woman named Alla Protassova. She was in Mozambique with her husband, a translator for the local Soviet trade mission. “Viktor is a very active, energetic person,” Alla told me. “He drags you in.” She moved back to Russia with her husband. Soon after, she left him, and in 1991 married Bout, who had returned to Moscow.

The Soviet Union dissolved that year. Amid a collapsing economy and Boris Yeltsin’s haphazard Presidency, criminal gangs, which had previously been confined to prisons, flourished. There were now many ways to become rich in Russia, but Bout was driven more by wanderlust than by money. He and Alla moved from Moscow to Sharjah, and launched the air-freight company. They were soon living in a spacious seaside villa.

In August, 1995, a few months after Bout started his partnership with Peter Mirchev, Taliban MIGs forced down one of Bout’s airplanes, near Kandahar. The Taliban took hostage the plane’s Russian pilots and crew. During the next year, Bout and officials from Moscow tried to secure the men’s freedom; Bout even met with the Taliban leader Mullah Omar. The Russians finally made it out of the country. The details remain elusive. Bout says that the crew escaped, and denies accusations that he cut a deal to shift his business from Rabbani and Massoud to the Taliban.

In 1997, Bout moved to Johannesburg. He and Alla, now the parents of a young girl, took up residence in a walled mansion with two swimming pools. Bout began seeking a runway, for business purposes, and in the process he befriended a white South African named Andrew Smulian. Fifty-six years old, Smulian had a phlegmy voice and a white mustache that hooked around his mouth. He owned an air-freight business that occasionally shipped arms.

Bout treated Smulian as a mentor, calling him babu—Swahili for “grandfather.” With Smulian’s assistance, Bout found an office and an airstrip in Pietersburg, two hundred miles northeast of Johannesburg, and established companies in Swaziland and Zambia. (Bout eventually built a network of thirty companies around the world; some of them were fronts, investigators say.)