Win It All is a 2017 American comedy film co-written, directed and edited by Joe Swanberg. Jake Johnson, who co-wrote the screenplay, stars alongside Aislinn Derbez, Joe Lo Truglio and Keegan-Michael Key. The film had its world premiere at South by Southwest on March 11, 2017. It was released on April 7, 2017, by Netflix. Plot Eddie Garrett is a gambling addict working as a parking attendant outside Wrigley Field. One morning Eddie finds Michael, a local thug, sitting in his kitchen. Michael asks Eddie to store a mysterious duffel bag, without opening it or asking questions, while he is in prison for six months, promising to pay Eddie $10,000. Eddie agrees, but a few days later gives in to temptation and opens the bag, finding several odd objects and a large sum of cash. Although advised by his addiction recovery sponsor Gene not to touch the money, Eddie eventually takes $500 from the bag and gambles it. He wins money, returns the $500 to the bag, and invites his friends to celebrate at the local bar. While there, Eddie meets Eva, a local nurse. They hit it off and Eddie makes plans to see her again. Feeling good, Eddie again gambles and loses all his profit. He begins a downward spiral of gambling that ends with him owing the bag over twenty-one thousand dollars. Desperate, he calls Gene for help and confesses his gambling. At first he mocks him, but finally decides to help. Eddie begins attending addiction counseling regularly and approaches his brother Ron for a job. Ron agrees to give him a job for six months, and if Eddie works hard and meets his obligations then Ron will loan him the money to pay the bag back. He shows up to work on time the next day and begins sorting his life out. He regularly pays the bag back and grows closer to Eva, even introducing her to his family. After six weeks of hard work Eddie gets an unexpected phone call from Michael in prison. He's being released early and will be over to retrieve his bag in a week. Panicked, Eddie approaches Ron and begs him for the money to repay the bag but Ron refuses, believing he wants to gamble. Eddie gets drunk and loses even more money from the bag before the casino bans him. Bottoming out, he goes to Gene's in the