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John DoughertyNovember 17, 2023
Paul Giamatti, Amy Ryan, Clare Foley and Sophie Kindred in a scene from “Win Win” (IMDB)Paul Giamatti, Amy Ryan, Clare Foley, and Sophie Kindred in “Win Win” (IMDB)

The Catholic Movie Club is a short weekly essay pulling out spiritual themes in our favorite films. You can discuss the movies with other readers in the comments on this page or in our Facebook group. Find past Catholic Movie Club selections here.

Jacob was left there alone. Then a man wrestled with him until the break of dawn…. The man then said, “Let me go, for it is daybreak.” But Jacob said, “I will not let you go until you bless me” (Gen 32:25, 27).

In the opening moments of “Win Win” (2011), a homemade stained-glass angel falls from its perch—suction-cupped to a child’s window—and breaks. It feels like a statement of intent by writer-director Tom McCarthy (“Spotlight”): He wants you thinking about angels, but maybe not the obvious ones.

The film’s protagonist, North Jersey lawyer Mike Flaherty (Paul Giamatti), isn’t an angel, but he is a good person. He’s a loving father, husband and friend; he goes to Mass on Sunday, and when he’s not advocating for senior citizens in the courtroom, he volunteers as a high school wrestling coach. But financial stress drives this good guy to make a bad decision. Mike becomes the legal guardian of a client (Leo, played by Burt Young) with dementia, claiming he’ll care for him at home per Leo’s wishes; instead, he installs Leo in a senior care facility while taking the monthly checks for being his “guardian.” Mike convinces himself that this is a harmless lie: Leo won’t miss the money, and the facility will take better care of him.

In Tom McCarthy’s film, the truly good things in life—love, trust, purpose—require hard, honest work.

But things get complicated when Leo’s previously unknown teenage grandson, Kyle (Alex Shaffer) arrives in town to live with him. Unable to contact Kyle’s mother in rehab, Mike and his wife Jackie (Amy Ryan) allow the boy to move in with them. Aside from the stained glass, Kyle is the film’s most angelic figure: He sports a halo of bleached blond hair, spindly wings tattooed on his shoulder blades, and that shy gentleness that teenage boys—despite their reputation—so often possess. (I work with them, take my word for it.) His arrival is accompanied by miracles: the joy he brings to Mike’s family and the preternatural wrestling talent he brings to Mike’s team.

At first, Mike thinks this is a “win-win:” Kyle will improve the team’s prospects while receiving a stable home life and education. You can tell that Mike hopes this extraordinarily good act will balance out his exploitation of Leo. But when Kyle’s mother, Cindy (Melanie Lynskey), arrives to bring him home, everyone will have to deal with the truth—and consequences—of Mike’s actions.

Just like Jacob wrestling the angel, the blessings in our lives are often the result of struggle. Those struggles look different for each of us, but often center on our fight to keep the faith and do good through the difficulties and doldrums of life. We may feel that the rewards for doing good seem paltry compared to the effort, especially if we look at our bank accounts. Mike is tired of wrestling: He wants the blessing without having to fight for it.

We all face that temptation, and like Mike, it becomes easy to convince ourselves that we’re entitled to cut a few corners: I deserve this. I need this. I’m not hurting anyone.

But it’s a lie. When we act selfishly—even if we tell ourselves it’s for a noble purpose—someone else is bound to get hurt. There’s no such thing as a “win-win” based on a lie. The truly good things in life—love, trust, purpose—require hard, honest work. You have to wrestle for your blessings.

“Win Win” is available to rent or buy on AppleTV+, Amazon Prime, and Google Play.

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