Hardball (2001)

Conor (Keanu Reeves) is a ticket scalper, gambler and, now, Little League coach for a rag-tag team of kids in one of the toughest part of Chicago. He's no role model, but his buddy Jimmy won't help him pay off his gambling debts unless Conor coaches Jimmy's corporately sponsored team. Surprising even himself, Conor becomes attached to his players -- and to their attractive schoolteacher (Diane Lane) -- and drawn into their tough and sometimes tragic lives.