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The word that best describes Mike Flaherty, and really every character in Tom McCarthy's big-hearted new film Win Win is that handy Yiddishism "mensch." Mike is a practicing Catholic, raising a family and maintaining a struggling elder law practice in suburban New Jersey, the kind of guy who always does the right thing even when it lands him in debt or coaching a losing high school wrestling team. The events of Win Win kick off when Mike makes an uncharacteristically immoral decision, but he never stops being a mensch, something that makes everything more complicated for him but makes up the warm center of this rich, endearing and honest comedy.
When he decides to take on the guardianship of his client Leo (Burt Young) Mike makes the tiniest false promise: instead of helping Leo live in his own home, as he requested, Mike leave him to the care of nursing home, something the dementia-addled Leo presumably wouldn't notice anyway. Mike doesn't tell his wife Jackie (Amy Ryan) that he's done this, which is complicated enough, but then suddenly arrives Leo's grandson Kyle (newcomer Alex Shaffer), a bleached-blond and sullen kid who swears his mom knows where he is but won't go back to Ohio when he realizes grandpa is in the nursing home. Seeing no choice in the matter, Mike and Jackie take Kyle in, Jackie getting over her immediate distrust of the kid she calls "Eminem" and Mike realizing he's in a lot deeper than he thought.
The movie's title is a little bit ironic, sure-- Mike is in trouble, and it's only going to get worse-- but there's actual winning there too; it turns out Kyle is a wrestling prodigy, and an addition to Mike's team who gives them the real possibility of a championship season. Though he's difficult and emotionally distant, something made even worse when his addled mom (Melanie Lynskey) comes to town, Kyle manages to bring out the best in everyone around him, from Mike's fellow coaches (Bobby Cannavale and Jeffrey Tambor, both hilarious) to even Jackie, who bonds with Kyle by showing the inked-up kid her Jon Bon Jovi ankle tattoo. It's hard to explain why none of this feels sentimental or unearned, but McCarthy's deft writing and his dynamite cast keep the film's tone earnest but just short of sappy.
There's never really any doubt about where the story is taking us, or that eventually Mike will pull it together to make things right, but the surprises in Win Win come from the plethora of well-drawn characters, who speak both bluntly and eloquently, who tease and love each other and who, though fitting well into this polished indie world, feel recognizable and real. McCarthy, who wrote the script along with his childhood friend Joe Tiboni, makes it all look so easy, especially with a cast that, led by Giamatti, hits every beat and laugh with precision. All that polish makes the sharper edges of Win Win harder to see, and McCarthy does skate over some potentially thorny issues in order to keep being kind to his beloved characters. Win Win isn't aiming for anything grand or life-altering, but sometimes it's almost better to see a simple and resonant story told so well.