Moscow would soon grow famous for operatic oligarchs and Byzantine intrigues, but Khodorkovsky never got caught in a compromising position — never snared at an Alpine resort, a Moscow casino or on a Riviera yacht. Girls, power, even the money, seemed to hold no magic. Where others basked in pomp, he was shy and painfully soft-spoken; you never heard his squeaky voice, a semitone deeper than Mike Tyson’s, at dacha parties for the foreign press, let alone on television. He divorced young but stayed on good terms with his first wife. Inna, his second, he met at the institute. Khodorkovsky was never flashy — he wore jeans and turtlenecks; the family vacationed in Finland — but he radiated the unlikely allure of a muscular technocrat. And yet, even at the top, he seemed adrift, unsure of his role in society. Unlike older Jewish oligarchs, men like Boris Berezovsky and Vladimir Gusinsky, who were often animated by old scores to settle, Khodorkovsky did not seem to consider himself an outsider. Lacking a public persona, he came to personify, by default, the revenge of the Soviet geek.

By 2000, Putin had entered the Kremlin. But Khodorkovsky — his net worth reportedly $2.5 billion — tried on a new role. He’d changed, he told colleagues. If in the past, Yukos and Menatep had exploited tax havens, stringing a daisy chain of shell companies across the offshore zones of Europe, Khodorkovsky now became an advocate for corporate governance. The first signs of an evolution had come under Yeltsin. In 1998, Russia suffered a crash — the state devalued the ruble, defaulted on $40 billion in bonds and cut its umbilical cord to the capital markets. Banks collapsed, the stock market tanked and the oligarchs turned desperate. Khodorkovsky, or so he told colleagues at the time, saw the need to reform. Companies that believed in transparency and shareholders’ rights, he now preached, did not fear lean times; they attracted foreign investment, and they grew. Skeptics abounded. It was, at the least, a timely conversion.

Even as Putin sought to curb the oligarchs, Khodorkovsky expanded his influence by new means. He brought in American firms like McKinsey and Schlumberger, experts in making the most of oil and profits. He also sought an insurance policy. Nearly a decade ago, he hired APCO, the Washington lobbying firm that employs former ambassadors and Congressmen. But in Putin’s second year in power, Khodorkovsky opened another front, setting up a foundation to support nonprofits and human rights groups. In the months before his arrest, he courted the administration of George W. Bush and power brokers like James Baker. His foundation recruited Henry Kissinger and Lord Rothschild for its board. He financed policy groups in D.C. and human rights activists at home, and to the joy of Laura Bush, he gave a million dollars to the Library of Congress. He joined the Carlyle Group’s Energy Advisory board, serving alongside Baker, and met — on separate occasions — with the elder Bush, Condoleezza Rice and Vice President Dick Cheney.

In Houston, Khodorkovsky dangled a 40 percent chunk of Yukos before the oilmen — the sale would have fetched billions and, possibly, ensured protection from the state. But in 2003, in a brazen affront, Khodorkovsky started to finance opposition political parties. Then that fall, he completed a megamerger, the union of Yukos and Sibneft, another Russian major, to create the world’s fourth-largest oil company. His rise was nearly complete. But all the while, as he told me in one exchange, he’d seen the warning signs. “I knew they’d arrest me,” he wrote. “I even spoke about it.”

In October 2003, Khodorkovsky boarded a jet in Moscow a near-wanted man. After a summer of saying goodbyes to friends and family abroad, he embarked on a farewell tour. It would be a second act in his new role, an audition in the hinterland. He went on the stump, lecturing on a newfound vocation: “Democracy.” To his surprise, the gamble proved a success — eight regions, dozens of appearances, mostly young people at every stop. He was even given the stage at a military college. Next up was a human rights forum in a Siberian city nearby. But before his plane could take off, the dark vans had formed a circle on the tarmac.

“WHO FEARS A FREE Khodorkovsky?” asked Marina Filippovna Khodorkovskaya, the defendant’s 75-year-old mother. “Forgive me if I’m blunt, but it’s Putin, and all those around him who stole Yukos.” Marina Filippovna comes to court as often as possible. A sturdy former engineer, she has never shied from speaking her mind. Asked by the BBC what she would do if she met Putin, Marina Filippovna replied without pause, “I would kill him.” “It’s not for me to say what led to all this,” she told me, as we stood together one morning, awaiting the arrival of her son, in the dilapidated Khamovnichesky District Court in central Moscow. She raised both hands to conjure the years of turmoil. “I only know this case is about politics and money. But which is more important, only those on high” — again she gestured, this time to the ceiling — “know the truth.”

The answer is unlikely to emerge in Judge Viktor Danilkin’s courtroom, a humble affair on the third floor of a squat building perched above the Moscow River. Each time I went to court, over the course of two weeks earlier this year, I sat a few feet from the defendant. It was a scene to boggle Kafka’s imagination.