He spent his 30s flying high as an oil executive and one of the magnificent seven, the group of Kremlin-connected oligarchs who controlled the commanding heights of Russia's economy during Boris Yeltsin's rule in the 1990s.
He spent his 40s in a prison colony, a convenient fall guy as President Vladimir Putin's entourage took control of Russia's energy sector.
But even as he was derided by the Kremlin-controlled media as an example of the crony capitalism that marked the decade following the Soviet collapse, Mikhail Khodorkovsky also became a liberal martyr -- a defiant and dignified symbol of the vindictive selective justice and legal double standards that mark Putin's Russia.
Khodorkovsky turned 50 this week
and thousands of well wishers from Russia and around the world sent him letters of support.
But even as marked that milestone, there were indications that the authorities are preparing a fresh set of charges that would keep him incarcerated indefinitely.
For many, Khodorkovsky's October 2003 arrest was the point when it became crystal-clear where Putin's Russia was headed -- and his fate has since been seen as a bellwether.
In many ways, Khodorkovsky's story is Russia's story. So what is his story telling us now?
On the latest "Power Vertical Podcast," I discuss the Khodorkovsky phenomenon and its larger meaning with co-hosts New York University's Mark Galeotti, author of the blog "In Moscow's Shadows,"
and Kirill Kobrin of RFE/RL's Russian Service, a contributor to the online magazine Polit.ru
Listen to or download the podcast above or subscribe to "The Power Vertical Podcast"