Writer-director Tom McCarthy excels at tales about men who feel isolated from their surroundings. In Win Win, it's Kyle, a teenager who enters the life of New Jersey attorney Mike Flaherty. Flaherty's journey begins when he represents Kyle's grandfather, Leo, who suffers from dementia. When Flaherty finds out about the substantial fee, he signs up as Leo's guardian, because he's been having trouble paying his bills. He and his wife, Jackie, meet Kyle when the kid shows up on his grandfather's doorstep. Kyle's mother is in rehab and her boyfriend is abusive, so Kyle wants to live with Leo. Because Mike placed him in a retirement home--against the man's wishes--he agrees to host Kyle for a few weeks, during which Mike learns about his wrestling skills and invites him to join the high-school team he coaches with Stephen. His best friend, Terry, offers to assist the duo to get his mind off his ex. When Kyle's mother shows up to collect her son and cash in on her father's situation, Mike risks losing everything he has gained.
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