After filming Pirates of The Caribbean, Jack Sparrow II (The first died during filming of the first fight scene with Orlando Bloom) spent his entire salary on fast women and booze!
After living on Isla de Muerta for a few months, hangover finally caught up with him, he sobered up and left the island. He was last heard screaming "But why's the rum gone?!" while sailing away into the horizon on board of the Black Pearl.

Feeling down on his luck, Jack Sparrow II, who had no money what so ever, felt forced to look for an honest job.
He didn't find one. Instead he found one of Black Jack's talent scouts (who were looking more for Jack's than for talent), and got signed up. He was payed 50,000 gold pieces and disappeared without a trace. The talent scout, believing he had lost all of Black Jack's money, went into hiding untill he, 2 months later, recieved a thank you letter, and his salary of 500 gold pieces from Black Jack. Jack Sparrow II had turned up to play for the team the date he was supposed to. In the mean time, his salary was completely gone, most likely spent on rum and women.
He now plays for team, being paid only in food and rum. In order to get women, he must play well.
Black Jack sure knows how to motivate his players!