Paul Giamatti (Barneys Version) plays Mike Flaherty, a New Jersey attorney with a struggling practice and mounting debt. When he finds himself with an opportunity to become legal guardian to Leo (Burt Young, Rocky Balboa), an elderly client suffering from dementia, Mike stifles his ethics for the $1,500 monthly payments. Promising the court he will allow Leo to continue living at home, Mike parks the old man in a nearby nursing home, pockets the money and doesnt breathe a word of it to his wife (Amy Ryan, TVs The Office).
The scheme hits a snag with the sudden arrival of Leos long-estranged grandson, Kyle (newcomer Alex Shaffer). Eager to keep things on track, Mike becomes a surrogate father for the troubled teen. The unexpected houseguest even proves to be another boon for Mike, as Kyle is a gifted wrestler, and the high school team Mike coaches in his downtime desperately needs the help.
Distinguished by strong performances and a generosity to its flawed characters, Win Win mostly avoids stumbling into domestic melodrama. Its funny and wise always a welcome combo and also very much a film of today, a tale of desperate measures in financially desperate times. Phil Bacharach