The movie Win Win follows the story of a struggling wrestling coach, Mike Flaherty, who takes on the legal guardianship of Leo, an elderly man with dementia, in order to earn some extra cash. However, things take an unexpected turn when Leo's troubled teenage grandson, Kyle, shows up on their doorstep.
Despite Kyle's delinquent behavior and disobedience, Mike sees potential in the young boy's wrestling skills and decides to enroll him in his high school team. Kyle proves to be an excellent wrestler and with his help, the team starts winning matches.
Amidst the triumphs and struggles with his wrestling career, Kyle's mother shows up and tries to take him back. But Kyle refuses to leave Mike's care, leading to a legal battle that threatens to tear the families apart.
As the story unfolds, Mike tackles his personal and professional challenges, ultimately learning some valuable lessons about responsibility, humility, and the importance of doing what's right.
The film was directed by Tom McCarthy and starred Paul Giamatti as Mike Flaherty and Alex Shaffer as Kyle, alongside Amy Ryan, Jeffrey Tambor, and Bobby Cannavale. It received positive reviews from critics and audiences alike, earning nominations for several awards including the Academy Award for Best Original Screenplay.