It is a story of malice, cruelty, and vengeance—but more than anything it is a story of a failure of imagination. Almost a decade ago, Mikhail Khodorkovsky, then the owner of the Yukos Oil Company and Russia’s richest man, completely miscalculated the consequences of standing up to Vladimir Putin, then Russia’s president. Putin had Khodorkovsky arrested, completely miscalculating the consequences of putting him in prison. During his eight years in confinement, Khodorkovsky has become Russia’s most trusted public figure and Putin’s biggest political liability. As long as Putin rules Russia and Khodorkovsky continues to act like Khodorkovsky, Khodorkovsky will remain in prison—and Putin will remain terrified of him.

Of his eight years without freedom, Khodorkovsky has spent more than half in Moscow’s Matrosskaya Tishina Detention Facility, a 246-year-old jail, where living conditions are far more punishing than those in a distant prison colony. He has declined to describe the conditions in which he has been kept in any but the most general terms, arguing that he is no different from other inmates, but those who have been held in the same place describe cramped cells with a hole in the floor that serves as the toilet. Inmates take cold meals sitting on their cots, a few feet from the hole. Access to the outdoors is virtually nonexistent. Khodorkovsky has spent a total of nearly three full years attending his two trials, transported to court and back in an armored car with a small holding compartment in which he must ride standing up and bent over. During the first trial, he and his co-defendant, Platon Lebedev, were made to sit in a cage, behind heavy steel bars. During the second trial, after a complaint was lodged with the European Court for Human Rights, they were displayed inside a Plexiglas cube.

At the root of the conflict between Putin and Khodorkovsky lies a basic difference in character. Putin rarely says what he means and even less frequently trusts that others are saying what they mean. Khodorkovsky, in contrast, seems to have always taken himself and others at face value—he has constructed his identity in accordance with his convictions and his life in accordance with his identity. That is what landed him in prison and what has kept him there.

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