‘Win It All’ Well-Acted, Poorly Plotted

Anyone who has watched the trailer of the new Netflix original “Win It All” knows exactly what unfolds in the first hour of the film. Gambling addict Eddie Garrett (“New Girl” star Jake Johnson) is tasked with storing a mysterious duffle bag in exchange for ten thousand dollars. Eddie opens the duffle bag, finds tens of thousands of dollars in cash stuffed inside, and gambles it all away. When he finds out that the bag’s owner is being released from prison early and wants his cash back, he gambles even more in a desperate attempt to get the money back. Even those who haven’t seen the trailer can tell what’s bound to happen as soon as he finds the first wad of bills in the bag––and so does Eddie, who cries out in a knowing mix of horror and exhilaration as soon as he catches sight of the cash.

The pervading sense of inevitability in this film is not necessarily a bad thing, as it mirrors the painful predictability of the cycle of relapse that many addicts experience. “Win It All” does an exceptional job of compellingly conveying the highs and lows of addiction. Johnson carries the film with his natural and nuanced portrayal of Eddie. With every twitch of his lip and furrow of his brow he is able to make visible the compulsions, delusions, and devastations that Eddie experiences every night at the poker table. A voice of exasperated reason comes in the form of Gene (Keegan-Michael Key of “Key and Peele”), Eddie’s irreverent, irresponsible, and oft-ignored Gamblers Anonymous sponsor, who points out the cruel humor of Eddie’s Sisyphean situation. “You lose, lose lose,” says Gene. “USDA prime-rib fucking loser! That’s the cut of you.” It’s as if Gene knows he can say exactly what he wants as harshly as he wants, because no matter what he does Eddie won’t listen. The film is most alive during Eddie and Gene’s interactions; it’s in these moments when the stakes can be felt most intensely.

But “Win It All” falters when it attempts to depict Eddie’s life outside of his addiction. Eddie’s older brother Ron (Joe Lo Truglio), a family man who runs a successful landscaping company, exists only to serve as a foil to his chaotic poker-loving younger sibling. Lo Truglio does his best with what he’s given, injecting as much life as he can manage into a largely flat character with painfully on-the-nose lines like “at a certain point, you have to grow up!” and countless variations thereof.

Eddie’s girlfriend Eva (Aislinn Derbez) is similarly one-dimensional. Everything that is ever revealed about her is reported rather than shown or felt. She is a nurse. She’s busy. She likes to take care of people. She is a single mother. Eddie tells Ron that “she’s the real deal,” that she’s “incredible” and “smart” and “cool,” but she isn’t given enough space or screen time to build herself into a real character. Her sole purpose in this film is to motivate Eddie to stop gambling, get a stable job, and––as Gene puts it––“get his shit together.” It’s a bad sign when a character could easily be replaced by a nice house or pretty piece of furniture that the protagonist really wants to save up for.

One of the potential challenges with gambling movies and their inherent predictability is that there’s generally only two ways for them to end: with a big win or a big loss. For a film like this one, which is driven more by character than plot, an unsurprising ending might not have been a big problem. But for some inexplicable reason, “Win It All” instead ends with a gimmicky twist that is completely bizarre and ultimately unsatisfying, cheapening a film that otherwise would have been a decent watch.