Meet Mikhail Khodorkovsky, Russia’s Freed Oligarch and Putin Foe

The Russian oil tycoon once presented a serious challenge to President Vladimir Putin, who threw him in jail for ten years

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From right: Hans-Dietrich Genscher of the liberal Free Democratic Party (FDP) welcomes Russian former oil tycoon Mikhail Khodorkovsky at Berlin's Schonefeld airport, on Dec. 20, 2013.

During a news conference on Thursday, Russian President Vladimir Putin made an unexpected announcement: Mikhail Khodorkovsky, once Putin’s greatest political foe who had been imprisoned for nearly a decade, would be freed “in the near future.” The next day, Khodorkovsky was released from prison four years before his sentence was to run out.

In the summer of 2002, just two year after Vladimir Putin originally came to power promising to rein in Russia‘s oligarchs, TIME wrote about Khodorkovsky in a list of People to Watch in International Business. “At 39, Khodorkovsky has amassed a $7 billion fortune and a reputation as one of the robber barons of Russia’s transition to capitalism,” TIME wrote. “But he’s working to clean up that image.”

(MORE: Khodorkovsky’s pardon: another sign Putin is winning.)

A little over a year later, Khodorkovsky was charged with fraud and tax evasion, the opening salvo in a decade-long legal battle that effectively removed him as a political threat to Putin’s power. Special forces troops surrounded Khodorkovsky’s plane when it stopped to refuel in Siberia, and he was dragged off to prison. “The dramatic move, part of an ongoing probe into Yukos, was seen by skeptics as a Kremlin-led effort to keep the tycoon, who has funded opposition parties, out of politics,” TIME wrote of Khodorkovsky’s arrest.

In the year before his incarceration, Khodorkovsky had funded opposition parties, and he was widely viewed as a potential challenger for Russia’s presidency. As the Russian government seized $13 billion of Yukos stock, Putin insisted that the case was about rooting out corporate corruption. But many wondered whether Khodorkovsky’s prosecution would turn him into a de facto opposition leader or a political martyr. “It’s very hard to tell how this one can end,” a Yukos board member said at the time. “If they let him out of jail, he won’t agree to be muzzled, and he doesn’t want to leave the country.”

Khodorkovsky was tried for the first time in 2004, while Putin cruised toward an easy reelection. In June 2005, Khodorkovsky was convicted of six of seven charges of fraud and tax evasion and sentenced to eight years in prison in Soviet gulag-like conditions. At Krasnokamensk, a Siberian labor camp, Khodorkovsky was denied any intellectual activity–no books; television only in the recreation room with other inmates. Once Russia’s wealthiest man, he performed manual labor for 16-hours-a-day. In the meantime, Yukos’s core assets were sold to an unknown company that was later bought by the state oil company Rosneft.

In 2006, a fellow prisoner slashed Khodorkovsky’s nose, claiming it was an accident. The director of the Federal Penitentiary Agency initially denied that the knifing occurred, then a few days later blamed Khodorkovsky for his own assault. Around the same time, what was left of Yukos filed for bankruptcy and was declared bankrupt the next year. “Now 42, Khodorkovsky may return to Russian society in his prime at 50, toughened by his experience and hungry for action,” TIME wrote in April 2006. “A charismatic modern leader could emerge. If he survives the camps, that is.”

When Putin ran up against constitutionally mandated term limits, his handpicked successor, Dimitri Medvedev was easily elected president, and Putin became the country’s prime minister. Dissidents expressed their dissatisfaction with Putin’s quasi-authoritarian rule. In March 2009, Khodorkovsky was back in court, facing new charges that he and a former business partner embezzled $25 billion. When he was convicted in December 2010, TIME wrote about the absurdity of the charges. The court found that Khodorkovsky stole 350 million tons of oil from his own companies, some of which never even produced the amount the court said he stole from them. “When faced with such nonsense, it is very hard to take it seriously,” Vadim Klyuvgant, the lead attorney for the defense, said during the trial. “Anyone who has watched this trial understands that it is just a farce.” The judge added six years to the eight Khodorkovsky was already serving.

After Putin returned to the presidency in 2012, in an election observers widely questioned, protests calling for reforms broke out across Russia and lasted for months. From his prison cell, Khodorkovsky wrote a column describing the impotent injustice of the country’s judicial system and why he still had hope for change.  “We are beginning to stand taller in the deceitful courts and on the streets of our cities,” he wrote. “We are still afraid, but now, even more than that, we’re ashamed in the presence of our children. And we can’t be made to bend anymore.”

On Thursday, Putin announced made the announcement that Khodorkovsky would be freed, and he was released from prison the next day. He traveled to Germany to visit his ailing mother, Marina, who had visited him every few weeks during his years of incarceration. In the latter years of his imprisonment, Khodorkovsky’s son Pavel became his father’s voice to the rest of the world. Pavel, who lives in the United States, founded the Institute of Modern Russia, a non-profit that advocates for strengthening the rule of law in the country. “I would like to thank everyone who has been following the Yukos case all these years for the support you provided to me, my family and all those who were unjustly convicted and continue to be persecuted,” he said in a statement. “I am constantly thinking of those who continue to remain imprisoned.”

In his announcement of Khodorkovsky’s pardon, Putin also declared amnesty for other high profile political prisoners such as two jailed musicians from the protest band Pussy Riot and a group of Greenpeace protesters. While some see the acts as an attempt to shore up Russia’s human rights record ahead of February’s Winter Olympics in Sochi, freeing his greatest political rival might be a sign that Putin is fully comfortable in power. As TIME suggested in 2006, Khodorkovsky has been released at age 50, indeed “toughened” by his experience. But seven years later, Putin may prove a foe too powerful now to be defeated.