Win It All

Eddie Garrett is a gambling addict who works as a parking attendant outside Wrigley Field to support his habit. One morning Eddie finds Michael, a local tough, sitting in his kitchen. Michael wants Eddie to store a mysterious duffel bag without any questions or tampering while he serves a prison sentence, and in return he will give Eddie ten thousand dollars. Eddie agrees to the deal, but a few days later, he gives in to temptation and opens the bag, finding several odd tools and materials and a large sum of cash.

Although advised by his addiction recovery sponsor Gene not to touch the money, Eddie eventually takes five hundred from the bag and gambles it. He manages to win money, and after paying back the bag he invites his friends to celebrate at the local bar. While at the bar Eddie meets Eva, a nurse at a local hospital. They hit it off and Eddie makes plans to see her again. Feeling good, Eddie again gambles and loses all his profit. Eddie 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 Gene mocks him, but seeing that Eddie is seriously in trouble he decides to help.

Eddie begins attending his 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 difference to pay the bag back. Eddie 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 bringing her to meet his family. After six weeks of hard work Eddie gets an unexpected phone call from Michael in prison. Michael tells him that 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 as he believes Eddie still wants to gamble. Eddie gets drunk and loses even more money from the bag before being banned from the casino. Bottoming out, Eddie goes to Gene's house in the middle of the night for help. Gene convinces Eddie to come to the meeting the next day.

After the meeting the next day Gene and Eddie stop at a diner. Eddie begs Gene to help and Gene finally relents. Seeing no other way out, Gene agrees to get Eddie into a high stakes poker game with the condition that if Eddie goes broke he will leave town. Eddie and a friend drive to the game with the bag and Eddie buys in for fifteen thousand dollars. After losing thirty thousand Eddie takes a break and panics, deciding the game is too wild to beat and that he has to run. He calms down and decides to put the rest of the money in the game at once. After playing for a while he wins a huge pot and is back up with a profit. He wants to continue playing but his friend insists he cash out. Eddie begins to argue but then clutches his chest and collapses. He is cashed out and driven to the hospital where he wakes the next day late for dinner with Eva's family. He talks Ron into driving him to Eva's house, and the movie ends with Eddie happily eating dinner with Eva and her family. Meanwhile, Michael is confused as to why he has four hundred dollars more than he started with.

• Jake Johnson as Eddie Garrett, a recovering gambling addict.
• Aislinn Derbez as Eva, Eddie's love interest
• Joe Lo Truglio as Ron Garrett, Eddie's older brother who runs a company and hires Eddie. Although supportive of his younger brother he is nonetheless exasperated over his antics and immaturaty.
• Keegan-Michael Key as Gene, Eddie's recovery sponsor
• Nicky Excitement as Nick
• Jose A. Garcia as Michael, a local thug who is going to serve a prison sentence and who entrusts Eddie with the bag
• Kris Swanberg as Kris

In August 2015, it was announced Joe Swanberg would direct the film, from a screenplay written by him and Jake Johnson.[1][2] It was later revealed Aislinn Derbez, Joe Lo Truglio and Keegan-Michael Key had been cast in the film, and secretly shot in Chicago.[3]

The film had its world premiere at South by Southwest on March 11, 2017.[4][5] It was released on April 7, 2017, by Netflix.[6]

• Win It All at IMDb
• Win It All at Metacritic
• Win It All at Rotten Tomatoes