Win It All 2017

Eddie Garrett, a gambling addict, works as a parking attendant outside Wrigley Field, leading a life marred by poor choices. One fateful morning, his tranquil routine is disturbed when a local thug, Michael, appears unexpectedly in his kitchen. Michael asks Eddie to keep a mysterious duffel bag for him while he serves a six-month prison sentence, promising a hefty $10,000 in return for his discretion. Temptation proves too strong, and merely days later, Eddie succumbs to curiosity, opening the bag to discover a collection of unusual items alongside a substantial amount of cash.

Despite the wise counsel from his addiction recovery sponsor, Gene, who strongly advises against touching the money, Eddie cannot resist the allure of quickly turning it into more. He daringly takes $500 from the bag to gamble, luck seemingly on his side as he wins and gleefully returns the cash. During this euphoric celebration at a local bar, he meets Eva, a charming nurse, and they share an undeniable connection, fueling Eddie’s hope for a better path.

However, Eddie’s fortunes take a turn as he plunges further into gambling, ultimately losing all his originally won money and now finds himself in a perilous situation, owing over $21,000 for the bag. In desperation, he reaches out to Gene, revealing his struggles. Although Gene initially mocks him, he decides to extend a helping hand, urging Eddie to face his addiction through counseling.

Determined to overcome his demons, Eddie seeks a second chance by asking his brother Ron for a job. Ron agrees, setting the groundwork for Eddie to earn back his integrity over six months, during which he must uphold his end of the bargain to receive a loan for repaying the bag. With renewed focus, Eddie becomes punctual at work, steadily addressing his financial obligations while nurturing his bond with Eva and introducing her to his family.

Just as Eddie begins to find his footing, he receives unsettling news: Michael is set to be released from prison early and will expect his bag back within the week. Panic seizes Eddie as he approaches Ron for assistance, but Ron, suspecting Eddie’s intentions may involve further gambling, denies his request. In a drunken haze, Eddie spirals downwards again, losing more than before and ultimately facing a casino ban.

Reaching his lowest point, Eddie visits Gene in the dead of night, desperately seeking help. Gene encourages him to attend a meeting where Eddie finds a sliver of hope. Afterward, they stop at a diner, where Eddie pleads for assistance. Gene finally agrees to help by entering Eddie into a high-stakes poker game under the condition that he must leave town if he loses everything. Armed with the bag, Eddie goes on to buy in for $15,000, but the game becomes tumultuous as he soon finds himself doubling that loss.

Once nearly defeated, Eddie gathers his composure and decides to put everything on the line in one go. After some intense gameplay, he ultimately hits a massive win that restores not only his funds but a sense of hope. However, conflict brews as his friend urges him to cash out, leading to a confrontation that culminates in Eddie suffering a heart attack, forcing a quick exit from the high-stakes environment.

A new dawn greets him in the hospital, where he awakens, late for dinner with Eva’s family. Convincing Ron to drive him, the film culminates in a heartwarming scene of Eddie joyously sharing a meal with Eva and her loved ones, while Michael is left bewildered by the unexpected extra cash he discovers upon his return, leaving audiences with an unexpected twist.