At the start of the film, Flaherty represents old man Leo Poplar (Burt Young, Rocky) in a lawsuit against the state of New Jersey. Leo needs a guardian in order to continue living alone; otherwise, he will be placed in an old folks’ home, which Leo does not want. A little out of touch, Leo cannot follow the legal proceedings very well, and Flaherty takes this opportunity to name himself as Leo’s guardian, cash in on the government’s assistance checks, and still place Leo in a home. Flaherty believes Leo will hardly notice the difference between his real home and the old folks’ home, and no one, including the state, will be the wiser. Leo’s grandson Kyle (newcomer Alex Shaffer) unknowingly enhances this idea when he shows up on the steps of Leo’s old house, looking to live with his grandfather.
Flaherty has no choice but to bring Kyle to his own home and sort out Kyle’s family drama. Kyle hints that he ran away from an absent and drug addicted mom and her loser boyfriend. This complication seems to make matters worse until Kyle accompanies Flaherty to wrestling practice. Kyle unwittingly shows off his outstanding wrestling skills (Shaffer is a successful high school wrestler in real life), and Flaherty uncovers an interesting fact about Kyle’s past: he used to rank at the state level before he quit wrestling at his old school. In this new environment, however, Kyle’s ready to take it up again. Flaherty is overjoyed, more money in his pocket and the solution to his team’s dismal record. This truly is a win-win situation.
By throwing a wrench into the normative daily activities of the Flaherty household, Kyle’s presence slowly affects the family for the better. Flaherty, a man who never was a bad person, just a good man who got a little selfish, warms up to Kyle and spends a good portion of the film digesting the choice that he has already made. But, Flaherty cannot undo what he has done, and, when it comes time, he will have to choose between money, possible disbarment, the abandonment of his family, and doing what is morally right. This film has a wonderfully light cadence that moves with grace to its inevitable, but not overly, predictable conclusion. Peppered with fun jokes and brilliant performances that are a pleasure to watch (notably Giamatti, Cannavale, and Shaffer), the overall result is a thoroughly enjoyable film. Win Win is a family-oriented dramedy that reflects modern family troubles: money, working through a recession, and not forgetting the important stuff amongst all of life’s stressors, which can be a tough thing to do. This film is a reminder to take a step back and appreciate what you have.
Win Win is finally available for internet or dvd rental!