This song is about a hustler going to a club or bar, saying, "I'm bad, I'll never win, but luck is luck!" So he puts in a lot of money. After everyone losing hundreds of dollars, the hustler goes on to another club, and another, and another, until someone catches on (another hustler/the devil). He challenges him, positive he'll win. He loses all his money to the first hustler, breaking his bad habit. That's just how I see it, sorry if it doesn't make sense.