Quite a few films about teen sports often focus on the man behind the team--the coach. In Win Win, we see that coach struggle with his own faults that he first sees as a moral good, but then digs himself into a deep hole that he almost cannot get out of.
Paul Giamatti plays Mike Flaherty, whose dayjob is as a lawyer. During his off hours he coaches the local high school's boys wrestling team, and unfortunately the team is not very good. One of Mike's cases involves the estate of an elderly man Leo (Burt Poplar) who needs increased medical care so cannot live alone at home anymore. When told that Leo's estate can pay someone for his care, Mike takes on this additional job as he needs the money for repairs to his office and basic needs.
At first Mike sees it as a win-win for both Leo and himself, both getting something they need. Then Leo's estranged grandson comes to visit, but really to escape the inattention and strained relationship with his mother (Melanie Lynskey). Teen Kyle (Alex Shaffer) begins to live with Mike's family when Mike sees that he is a pretty talented wrestler. Naturally Mike recruits him for his team, which begins winning, and he becomes lax in his attention to Leo and mistakes are made. This slippery slope gets more slippery when Kyle's mother comes to claim him.
Giamatti is both wryly funny (and convincing as a coach) yet teetering on the edge of having everything going wrong all at once--a man who feels like he is going under with too many problems, some which he created himself. But Mike still comes off as a good and well-meaning man who is trying to do his best and not necessarily a bad person who is opportunistically taking advantage of things that have come his way, even though that is exactly what he is doing.
The character of Mike's wife, played by Amy Ryan, is more broadly scripted than I expected. As the wife she has to be the one who, compared to Giamatti's character, has to be the more levelheaded one to offer us the other side of any argument. Bobby Cannavale has the most humor as a friend/assistant coach who relishes being in Kyle's aura. He provides a lot of the comic relief, as does Jeffrey Tambor as Mike's law partner, who also wants to get into the wrestling game and finagles his way onto the coaching team.
The only actor I think that was not chosen well is Melanie Lynskey. Her dainty voice and face belies her irresponsible and uncaring character and I don't think the script made her out to be anything more than the villain. There were tiny moments when I started feeling sorry for her, but they were not real enough for me to sympathize with her, and at film's end I wondered if she was playing all along or has some morsel of decency. Although this ambiguity could be interesting, I don't think it was fleshed out enough.
How her situation ends up was also too pat (although it truly is a win win for everyone involved I think) and I expected something more serious and a bit messy. Alex Shaffer I think did an especially good job (this is his first real acting role), playing both stoic and easy going, so for Kyle to display any hint of emotion, like a small smile or a tear, feels like it is a big deal for his character to even show that much. When he explodes you know his anger has been pent up a long time. At first he comes off as a teen with loose values but you can tell he is a really, really nice kid despite his faults (which actually are not that bad; perhaps this is a parallel of Mike's character). His true love and talent for wrestling infects his losing team and coaches too and he is a catalyst for the (eventually positive) changes to everyone around him.
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