Legit (2006)

When a routine money drop goes awry, Big Jim Cartoni decides to do the unthinkable: get out of the mob. Acting on his dream of opening his own club and going legit, he's foiled at every turn by lifelong nemesis, Joey Moran, all the while hoping his boss doesn't find out about the club until it's a success. With the city of Chicago as its' backdrop, follow the story of one man who tries to beat the odds without ever having to fix the numbers.

Unfortunately the movie Legit is not yet available on HBO Max.