For financial benefit, a lawyer on the verge of losing his practice becomes the guardian of a wealthy elderly man, and somehow ends up raising his teenage grandson.

Rating: 7/10 (9 June 2014)

Mike Flaherty (Paul Giamatti), is a struggling lawyer and volunteer wrestling coach who offers to become an elderly man's guardian for the financial benefits. Flaherty claims that he wishes to become his client Leo's guardian to ensure that his wish of living at home can see fruition, but soon realizes it would be too much work and sends him to a retirement home. He is free and clear until Leo's grandson Kyle comes to town to stay with his grandfather, but instead ends up living with the Flahertys. The entire family soon bonds with Kyle, and to Mike's surprise he is a wrestling sensation, but all secrets come out eventually.
'Win WIn' is charming in the sense that it deals with normal people and everyday life. In the movie Paul Giamatti's family has money problems that need a real solution. This issue, which cannot be solved in a three minute montage with 'Push it to the Limit' playing in the background forces Giamatti's character to make the wrong decision for the right reasons. That decision's weight on his conscience is inevitably what makes him take in Leo's grandson Kyle thus redeeming himself as a likable character. Writers Koe Tiboni and Thomas McCarthy do a wonderful job creating characters with real flaws the audience can relate to thus creating the feeling that characters on the screen are as human as themselves.
Paul Giamatti and Amy Ryan both fit perfectly into their roles as suburban parents, and in his first performance Alex Shaffer manages to hold his own with the veteran actors. The somewhat unbelievable story is told in a manner that does not leave the viewer asking questions like "can that really happen," or "would they really do that?" "Win Win' is not a laugh out loud dramedy (drama/comedy), but it is darkly humorous. While you are rooting for the Flaherty family, you also secretly wish them some mild misfortune because whether it be a panic attack while jogging, or a teenager out wrestling an adult, sometimes it is just nice to laugh at the misfortune of others. Watching Mike Flaherty both deceive Leo and care for Kyle,'Win Win' truly shows us that what a person will do for their family is astounding, but what they will do for a total stranger, now that's beautiful.