A cash-strapped lawyer tries to squeeze some lemonade out of the lemons of his poor decision-making in Win Win, a charming and funny movie about family life.
Business isn’t great for Mike Flaherty (Paul Giamatti), a lawyer who specializes in working with the elderly. The building that houses his office needs repairs, he has bills that need paying and he has a lot more empty hours than he has clients. His other main occupation — the high school wrestling team he coaches with friend Stephen (Jeffrey Tambor) — isn’t going that great either. The stress from it all even has him suffering from occasional panic attacks, such as the particularly embarrassing one he has while running with his friend Terry (Bobby Cannavale), who himself is simmering with rage over the divorce he’s in the middle of.
In this beleaguered state, Mike goes to court to act on behalf of Leo Poplar (Burt Young), an old man whose encroaching dementia means it’s likely time he will have to leave his home and become a ward of the state. But Leo doesn’t want to leave his house and Mike just happens to see the custodian fee — $1,500 per month — that will go to whomever takes care of Leo. So Mike says he’ll be Leo’s legal guardian and help the man stay in his home. The judge agrees and Mike promptly takes Leo over to a nursing home. Leo’s estate pays for the nursing home, Mike gets the custodian fee, the court’s never the wiser and Mike’s financial situation has a chance at improving.
And then Kyle (Alex Shaffer) shows up.
The 16-year-old grandson Leo didn’t know he had, Kyle is the son of Leo’s daughter Cindy (Melanie Lynskey), whom the court and Mike couldn’t find when they initially looked for other caretakers for Leo. Possibly because she’s now in some kind of rehab program and Kyle, who we piece together was left with her boyfriend, now has a black eye and a strong desire not to go back.
Mike isn’t sure what to do but, after being initially resistant, his wife Jackie’s (Amy Ryan) maternal instincts take over and they take Kyle in. A stay-at-home mother of two younger children, Jackie quickly takes to Kyle (at several points saying she’d like to beat up Cindy for abandoning him). Mike and Kyle also get along, particularly when Mike takes Kyle to wrestling practice. Turns out, Kyle is an excellent wrestler — one who had a promising future in the sport back in his hometown. Soon, Kyle has enrolled in school, joined Mike’s team and become a happy member of the family (which is better provided for thanks to that money for Leo that nobody but Mike really knows about).
What could go wrong?
Giamatti is great at playing these characters — the basically decent guy who makes a bad choice here and there and has to deal with the consequences. Watching Mike sort of deal with himself is part of the pleasure of this movie. In some ways, Mike is the moral center Kyle has always needed. But we also know that when his scammy treatment of Leo is uncovered it will go hard with this much-wronged boy.
The other great pleasure of the movie is watching Mike’s relationship with his wife and with his friends Terry and Stephen. All of the actors are good at giving such strong, nuanced performances that just watching them talk about nothing over the kitchen counter is kind of a thrill.
Win Win is at its heart about the nature of families — how they come together, what can pull them apart. In the kind of darkly funny way you expect from a Paul Giamatti movie, Win Win is sweet and charming. B+
Rated R for language. Directed by Thomas McCarthy and written by McCarthy and Joe Tiboni, Win Win is an hour and 46 minutes long and distributed by Fox Searchlight Pictures.