Mike Flaherty is a decent husband (except that he won't pay someone to chop down the dead tree in the front yard), a good boss (except that he can't stomach shelling out $6,000 to fix the boiler), and a good lawyer (he chose to help old people instead of get rich). Now he's feeling suffocated by his own sense of moral obligation.
In Win Win (rated R for language), Mike (Paul Giamatti) shows how delicately we justify our own self-interest by saying we're just "doing the right thing." Mike becomes guardian to an old man because it's the right thing to do and because he could use the money. He takes in the old man's grandson Kyle, a youth (Alex Shaffer) whose monosyllabic conversation style belies his openness to love, because the kid has no place to go except back to his drug addict mother. And because Kyle's wrestling skills might finally help Mike's team win a match.
Win Win's subtle script and its gentle, funny cast has both quirk and pathos. Giamatti portrays the tubby, beleaguered character he often plays so well. Amy Ryan brings her usual warmth to the role of Mike's wife, Jackie. Unlike her husband, Jackie does the right thing whether she gets a trophy out of it or not. Some of the movie's comic strength lies with its vivid minor characters. Mike's friend, Terry (Bobby Cannavale) may be a type of a tanned New Jersey jughead, but he also possesses his own neediness and oblivious hilarity.
The moment when Mike's team may win its first match is the big sports climax writ small, with a once half-hearted team and its worn coach trembling at the possibility of just one victory. Win Win dwells in those small moments of victory and compromise.