Chicago, 1954. A kid with self-doubt, Jesse Cruz spends his days drinking beer and playing ball with his friends. At night, they commit petty crimes to supplement their income.

One night, Jesse sees a man slumped over the steering wheel of his car. He's been shot. Swinging into action, he takes the wounded man to the pool hall where he and the guys hang out. Mob assassins show up to finish the kill, but Jesse knows where the house gun is kept and gets the drop on them.

The wounded man turns out to be a mob boss, and soon, Jesse and his crew find themselves working for him, moving up the ranks and being given more essential jobs. But in the end, will Jesse be able to get over his self-doubt and become the Boss?