Revolver (2005) on Netflix

Jake Green is a hotshot gambler, long on audacity and short on common sense. He's rarely allowed to play in any casino because he is a winner. Jake has taken in so much money over the years, he is the only client of his accountant and older brother Billy. One night, Jake, Billy and their other brother Joe are invited to sit in on a private game, where Jake is expected to lose to Dorothy Macha, a crime boss and local casino owner who can't play for squat, but always wins because people are too scared to beat him. Jake isn't afraid of Macha, and not only beats Dorothy in a quick game of chance, but takes every possible opportunity to insult the man. Jake and his brothers leave the game, and Macha puts out the order for a hit on Jake, who ends up working for and being protected by a pair of brothers, Avi and Zack, who are out to take Macha down.