Win It All
A cloak-and-dagger infusion of money is exactly what gambling addict Eddie Garrett (Jake Johnson) does not need in WIN IT ALL. But when an old friend asks him to keep a zipped-up-tight duffel bag while he's serving a 6-9-month prison sentence, Eddie is quick to say yes. Especially when Eddie's "fee" for safeguarding it will be $10,000. Of course, he promises, he won't open it. Eddie stashes the bag, goes about his business: parking cars; visiting his upstanding brother, Ron (Joe Lo Truglio); connecting with his ever-patient Gamblers Anonymous sponsor, Gene (Keenan-Michael Key); even introducing himself to the beautiful Ava (Aislinn Derbez), the woman who could be "the one." Still, that duffel calls to Eddie. What could hurt? He'll just take $ 5,000 of the vast fortune he finds in the bag. And he'll put it right back! Unfortunately, putting it back is not in Eddie Garrett's DNA. Losing a bundle is. So, when that same old friend calls back to let Eddie know he's being released from prison early, Eddie's number -- and not his lucky one -- is, is up. He has only days and very few resources to put back all that he's gambled away. For Eddie, it's a race to save his newly-found abstinence, a relationship that just might be perfect, and maybe even his life. Everyone in his life (and in the audience) wants him to survive; it's only Eddie who sabotages his own redemption.
Starring
Jake Johnson, Keegan-Michael Key, Joe Lo Truglio
Director
Joe Swanberg