Mike is in a one-man law office, where most of his clients are senior citizens. He shares the small building with an accountant-friend, “Vigman” (Jeffrey Tambor), where they worry about leaky plumbing, and share a secretary who fusses about not having enough money to pay the cleaning service. Obviously, Mike isn’t terribly successful, but he’s a nice guy who seems to mean well. He coaches the local high school wrestling team with his old friend “Vigman,” but they don’t know what they’re doing, and the team is terrible. He has another good friend, Terry (Bobby Cannavale), but he’s just-divorced and out of work and struggling a lot emotionally right now.
Mike realizes that he has cash flow problems in his practice, and tries calling in a few chits to see if he can get any referral business, but that’s a dry hole, also. Somewhat desperate to maintain appearances, even with his wife, he cuts a corner on a court case. It seems that the State was all ready to declare Leo (Burt Young) mentally incompetent. They couldn’t find the daughter, he’s descended into dementia, and though he can pay for someone to come to his home and take care of him, and doesn’t want to leave his home, there’s nobody to administer the details of all that, to be his official guardian. Mike, seeing an opportunity to improve his cash flow situation, assures the judge that he will personally be the legal guardian, but then moves Leo into a nursing home while pocketing the stipend. Nobody’s the wiser, right?
But one day a teenage boy, Kyle (Alex Shaffer) shows up at Leo’s door, claiming he’s the grandson. This is news to Mike. Also to Leo, but then, it’s hard to tell what he remembers. Kyle says his Mom is in rehab back in Ohio, and he’s come to New Jersey to meet his Grandpa, and to stay with him for a while. Mike, scrambling to keep his little secret scam going, manages to stir up his wife’s maternal instincts, and they wind up taking in Kyle, at least until his Mom gets out of rehab.
Slowly, the surly starts to wear off of Kyle. He turns out to be a nice kid, though terribly neglected, and starving for some attention and affection, and any semblance of a family life. He also turns out to be a fantastic wrestler, much to everyone else’s surprise. It’s all fun until Kyle’s Mom, Cindy (Melanie Lynskey) actually does show up, with a lawyer (Margo Martindale) in tow and demanding to know why she’s not the legal guardian, and the recipient of the accompanying stipend.
Now everything’s even more of a mess. Everybody’s upset at Mike for the subterfuge, including Kyle, who feels betrayed again. Ever-loyal Jackie isn’t happy, either. Can our oh-so-normal characters find a way out of this moral quagmire? Well, strangely enough, we are rooting for them to do just that, because despite the flaws of these families, we want them to emerge from the ashes, because we like them, anyway, and because we realize we’re all flawed, it’s just that some sins are more evident than others. And some are more forgivable than others.
“Win Win” isn’t really a comedy, though there are some humorous moments. It’s more of a character study disguised as a family drama. It feels real, and genuine, completely human, and therefore deeply needy of redemption.
Ronald P. Salfen is co-pastor of United Presbyterian Church, Greenville, Texas