Nothing much happens in Win Win, but this is still one of the most joyous and life-affirming family dramas we’ve seen in a while. The always reliable Paul Giammati plays Mike Flaherty, a small town lawyer struggling to make ends meet in today’s tough economic climate. He doesn’t have many clients, the building he’s in is falling apart and his furnace is on the blink. But worst of all, he’s simply too afraid or proud to tell his wife Jackie (Amy Ryan) that he can’t afford to fix any of it. Mike’s health is taking a hit too, as he collapses while jogging with his best friend Terry (Bobby Cannavale).
The story's real conflict though, comes in the form of a choice made by Mike. Something he does that’s not very ethical but seems harmless enough. Through a desperate act of legal manoeuvring, Mike assumes the care of an aging client named Leo (Burt Young)—who suffers from dementia—just so he can get his hands on the old man’s money. And rather than personally attending to Leo's needs, Mike puts him in a care facility. Mike would likely get away with his plan were it not for a couple of complications. The first comes in the form of Leo’s grandson, Kyle (brilliant newcomer Alex Shaffer sporting a scene-stealing blonde hairdo) who was dumped on the old man by his drug-addict of a mother (Melanie Lynsky). Mike’s initial thought is to send the boy home. But when he finds out the kid was a state champion wrestler back in Ohio—and Mike happens to coach the school’s wrestling team—Mike sees it as a win-win situation for both himself and the boy. Until Kyle’s mom shows up wanting both the boy and her father’s money.
There are also a lot of little happenings going on throughout the film, but director Thomas McCarthy keeps everything so subdued, provincial and low-key that the whole thing seems effortless. Thanks to the straight-laced script that doesn’t make any moral judgment on the characters and McCarthy’s smart move to keep the amount of money that Mike is “swindling” low enough, we can almost sympathize with Mike’s indiscretion. While Giamatti is in top form, it is McCarthy’s deceptively clever handling and acute casting (Shaffer and Ryan are standouts here) that makes Win Win an all-round solid film. This is a no-lose proposition.