Win Win, starring Paul Giamatti, Amy Ryan, and Burt Young, is a fish out of water story of sorts, although it’s not the typical stranger in a strange land tale. Instead the tables are turned, and the perspective is from the visited instead of the visitor. It is a point of view previously explored by director Tom McCarthy in his 2007 film The Visitor. In that movie Richard Jenkins plays a man who befriends illegal immigrants who are squatting in his seldom used New York apartment. In Win Win Paul Giamatti plays a man who is thrust into an unplanned informal adoption of a wayward teenage boy. The film effectively explores human emotions and actions in a lighthearted yet touching way.
Mike Flaherty (Giamatti) is a lawyer whose practice is on the verge of collapse. Most of his clients are elderly people who are in need of some type of assistance. Mike represents their interests in court when they become unable to care for themselves and are facing guardianship or placement in a nursing home. Mike is desperate for money, but he is not a desperate man. He is happily married, has two kids, and is a volunteer wrestling coach at the local high school. His life would be good if he could just manage to make ends meet. He sees an opportunity when he realizes one of his wealthier clients, Leo Poplar (Young), pays a guardian fifteen hundred dollars a month. He steps up to take the role of Leo’s guardian under the guise that he wants to help Leo remain independent rather than being sent to a retirement home.
Mike double crosses Leo and sends him to a retirement home anyway, while collecting the cash. Mike doesn’t feel that bad about his decision. Leo is not a ward of the state, and the retirement home he lives in is nice and comfortable. Mike’s contentment in his decision is turned upside down when Leo’s long lost grandson Kyle (Alex Shaffer) shows up. Mike and his wife Jackie (Ryan) decide to take the teenager in when they learn his mom is a drug addict currently in rehab. Mike coaches his local high school wrestling team and as it turns out Kyle is a pretty good wrestler. As relationships form between the Flaherty’s and Kyle, as well as Kyle and Leo, Mike is faced with the consequences of his actions.