Media playback is unsupported on your device
29 July 2015 Last updated at 02:23 BST
Now he finds himself with a death sentence after having been in prison for almost four years.
BBC News charts the rise and fall of Colonel Gaddafi's favourite son.
Video by: Mohamed Madi
Not too long ago, playboy Saif al-Islam Gaddafi was heir-apparent to an oil-rich dictatorship.