Lando Calrissian's youth has been speculated in many places, some think he was a clone leftover from the clone wars, others say that he was a Jedi who left the order and used his powers to win at gambling.  Due to all the rumors, no one is sure what to belive anymore.  At the age of 27 he was already a professional gambler, and a pretty darn good one, stealing fortunes from rich tourists on luxury liners such as The Queen of the Empire.  He couldn't even pilot a starship when he won the Correllian starfighter known as The Millenium Falcon in a game of Sabacc, and decided to try to learn to fly her.  His instructer ended up being a spice smuggler named Han Solo.  He arived on Nar Shadaa, and stood off against Boba Fett, earning eternal hatred from Boba Fett, and free piloting lessons from Solo.  Had he known where this was going, he would have found someone else.  After learning the basics, he went to the central systems to win some more money, gambling.  He won the starfishdriod, Vuffi Raa, end made an enemy worse then Boba Fett when he Rokur Gepta, the Croke turned sorceror of Tund.  His discovery of the hidden civilation on Rafa earned him a taste of fame outside the world of gambling.  He struck it rich selling the Rafan life crystals, but lost the fortune as he did many other things, including his ship to his own teacher in the same game he won the YT-1300 type ship.  3 years after the battle of yavin, he met his old instructer only to reveal the Darth Vader and Boba Fett had already gotten there, and Han got sealed in carbonite.  A year later he helped Princess Leia free Solo from Jabba's palace.  He then destroyed Death Star II and became a military hero.  1 year after Endor, Jabba's parent, Zorba, beat him in a game of Sabacc game, in which he cheated and lost Cloud City.  After the Zorba fiasco he became the chief administrator of Hologram Fun World. He reclaimed his military title to fight the cloned Emperor.  He later was enlisted to help Luke Skywalker find students for his academy, resulting in Calrissian winning a 1,000,000 credit reward from a grateful Duchess.  He carried out many other missions for the NR, but now that the Yuuzahn Vong invasion has happened he has little to lose, because of his empire of investments crashed.