Win Win (film)

It stars Paul Giamatti as a struggling attorney who, volunteering as a high-school wrestling coach, takes on the guardianship of an elderly client in a desperate attempt to keep his practice afloat.

Small-town New Providence, New Jersey, attorney Mike Flaherty moonlights as a wrestling coach and struggles to keep his practice solvent, while shielding his wife Jackie and their two young girls, Abby and Stella, from the extent of the problem.

When his court-appointed client, Leo Poplar, who is suffering from early dementia, turns out to have no locatable relatives, he persuades a judge to appoint him as guardian, for which he will receive a stipend of $1,508 per month.

Kyle tries to break into Leo's old house, and when Mike and Jackie question him about it, he reveals his troubled family life: His mom is in rehab, she lives with her boyfriend, and he does not want to go back.

Realizing the mistake of his earlier actions, and seeking instead to do what is best for both Leo and Kyle, Mike offers Cindy the monthly stipend in exchange for leaving them in his care.

"[6] Kenneth Turan of the Los Angeles Times called it "McCarthy's most polished and successful film to date, as well as a bit of a risk" and lauded Giamatti's performance, stating that he "has always had a gift for creating intense empathy for sketchy characters, an ability that has never been more essential than it is here.

"[8] Roger Ebert of the Chicago Sun-Times gave it 3 out of 4 stars, writing "You have a funny situation, and there's some truth in it and unexpected characters, well-acted, and you may not have a great film but you enjoy watching it.