The film revolves around Mike Flaherty, a small-town lawyer in New Jersey who is facing financial difficulties. In a desperate attempt to resolve his financial problems, Mike takes on the role of the legal guardian for Leo Poplar (Burt Young), an elderly client with early-stage dementia. Mike places Leo in a nursing home, allowing him to collect the monthly stipend as Leo’s guardian.
The climax of the film occurs when Mike’s scheme is jeopardized with the arrival of Kyle (Alex Shaffer), Leo’s teenage grandson from Ohio. Kyle is a talented high school wrestler seeking refuge from his troubled home life. Mike and his wife Jackie (Amy Ryan) decide to take Kyle in, hoping to provide him with stability and support.
As Kyle becomes a member of the Flaherty family, he also becomes an asset to the high school wrestling team, coached by Mike. The team experiences unexpected success with Kyle’s exceptional wrestling skills.
In the resolution, the film delves into themes of morality, responsibility, and the consequences of one’s actions. The characters confront the ethical choices they’ve made, and the story explores the impact on both the Flaherty family and Kyle.
“Win Win” is celebrated for its heartfelt portrayal of human relationships, its exploration of moral dilemmas, and its blend of humor and drama. The film received critical acclaim for its performances, particularly Paul Giamatti’s nuanced portrayal of Mike, and its authentic depiction of family dynamics.