The first indication is the opening scene in which Mike Flaherty (Giamatti) is jogging on a woodland New Jersey road. Though we only see the back of his head, we have no doubt it is he, when two fellow runners breeze by. The rest of world is also leaving him in the dust. His storefront law practice is falling apart … literally, client by client, boiler by bathroom. He moonlights as the coach of the local high school wrestling team, which has yet to win a game.
What he does have is a loving wife, Jackie (Amy Ryan), and two adorable daughters. Still, the operative word, voiced throughout the family, is “sh-t.” Out of the blue, a number of “win-win” situations come his way. A senile client, Leo (Burt Young), is declared incompetent by a judge. Unable to locate his sole heir, the court is poised to relegate him to a nursing home, when Mike jumps in the fray. As newly-appointed guardian, Mike is supposed to oversee him in Leo’s own house. However, Mike puts him in the nursing facility anyway and pockets the $1,500 a month stipend. Then, fortune appears a second time in the person of Kyle (Alex Shaffer), Leo’s runaway grandson. Brimming with teen angst, Kyle would seem to be a problem, except he happens to be a champion wrestler. Mike enrolls him in the school and starts the team winning.
Instantly, everything unravels, but the worst of it is that Mike loses the trust of Jackie and Kyle … mainly Kyle, who is just starting to believe in something.
As in “Sideways” and “Barney’s Version,” Giamatti’s character takes us deep into “The Dark Side.” How he does it by making us laugh is where his art lies. And it doesn’t hurt the he is helped by an excellent supporting cast, including Jeffrey Tambor and Bobby Cannavale as assistant coachbuddies (Stephan and Terry).
Written and directed by Tom McCarthy (“The Station Agent”), “Win Win” is another immaculate vehicle for Giamatti. Such an appealing schlemiel, he makes misery almost seem worthwhile.