Win It All

Eddie Garrett, a dedicated parking attendant, struggles with a gambling addiction that severely impacts his daily life. Living outside Wrigley Field, his choices lead him into a cycle of poor decisions and mounting debts.

Eddie's mundane life takes a sharp turn when Michael, a local thug, unexpectedly appears in his kitchen. Michael asks Eddie to store a mysterious duffel bag for him while he serves a six-month prison sentence, enticing him with a promise of $10,000 for his discretion.

Despite knowing better, Eddie's curiosity overwhelms him, and just days later, he opens the duffel bag. Inside, he finds an assortment of unusual items accompanied by a substantial amount of cash, which sets off a chain of impulsive decisions.

Ignoring advised caution from his recovery sponsor, Gene, Eddie takes $500 from the bag to gamble. His luck appears to change as he wins, which leads him to feel invincible and celebrating at a local bar after returning the cash.

At the bar, Eddie meets Eva, a charming nurse, and they share an instant connection that gives Eddie hope for a brighter future. This newfound relationship thrives as Eddie starts believing he can overcome his addiction.

Eddie's gambling addiction resurfaces, and he quickly loses all his previously won money, now facing a debt of over $21,000 for the bag. Out of desperation, he confides in Gene, who initially reacts with mockery but ultimately offers support.

Determined to rebuild his life, Eddie asks his brother Ron for a job, leading to a six-month plan to regain his integrity. Ron agrees, believing in Eddie's desire to change and repay the debt responsibly.

Eddie starts to make substantial changes, showing up on time and diligently addressing his financial responsibilities while growing closer to Eva. This period allows him to mend relationships, including introducing Eva to his family.

As Eddie begins to stabilize his life, he learns that Michael is being released from prison early and wants his bag back within a week. Panic ensues for Eddie, leading him to turn to Ron for help, but he is turned away, raising his anxiety levels.

Spiraling once more in a drunken haze, Eddie engaged in reckless gambling, ultimately receiving a ban from a casino. This marks one of his lowest points and forces him to confront his escalating addiction head-on.

In the dead of night, Eddie seeks out Gene, hoping for guidance and a way back from his reckless path. Gene encourages Eddie to attend a support meeting, offering a glimmer of hope amidst his turmoil.

After attending the meeting, Gene agrees to help Eddie by entering him into a high-stakes poker game, setting a condition that Eddie must leave town if he loses everything. Eddie invests $15,000, hoping for a turnaround.

During an intense poker game, Eddie faces significant losses but gathers his resolve and bets everything. After a series of nail-biting moments, he manages to secure a massive win, reigniting hope for a fresh start.

Just as Eddie celebrates his victory, a confrontation with a friend pressures him to cash out. The stress culminates in Eddie suffering a heart attack, forcing him to exit the high-stakes environment abruptly.

Eddie wakes up in the hospital after his heart attack, missing a dinner with Eva's family. With Ron's help, he rushes to join them, solidifying his renewed commitment to life and relationships despite Michael's newfound confusion over the extra cash.