Win It All is a drama come comedy type of film written, produced and directed by Joe Swanberg. It sees Eddie Garrett, played by Jake Johnson, left with a very mysterious duffel bag by local tough guy Michael, who is heading to prison for 6-9 months. Eddie is due to be paid $10,000 on Michael’s return from prison but he must put the bag to one side and forget about it. He’s not in any circumstances meant to open the bag to see what’s inside it, even when temptation kicks in.
As you’d expect a few days later Eddie let’s temptation get the better of him and he opens the bag to discover the contents that lay inside. There are tools amongst other things but there’s also cash and for a gambling addict like Eddie this is bad. He then sets about on a journey where he decides to lend himself $500 dollars to gamble with. This is against the advice of Gene, his sponsor from the addiction program that Eddie is on.
Eddie comes up trumps and not only gets the $500 back but he manages to be well in profit too. Obviously, this is the start of a downward spiral as while on such a high Eddie meets a woman who he hits it off with called Eva. While floating on the crest of a wave he decides to gamble more, especially after his success the first time around. By the end of his latest run he ends up being in debt to Michael’s duffel bag by over $21,000.
With nowhere else to turn, Eddie asks his sponsor Gene for help and although at first Gene mocks Eddie and his decision to gamble so much money, he does eventually help him. Eddie starts back attending his addiction counselling program regularly and he gets a job with his brother who agrees to lend him the remaining money needed if he works hard for 6 months. This all seems great before Michael phones Eddie from prison and says he’s being released early. Eddie’s brother Ron refuses to lend him the money as he thinks he’s back gambling so there seems to be no way out.
Eventually, after losing even more money gambling, Eddie gets into a high stakes poker game through Gene as a final throw of the dice. Eddie must win or he will have to leave town and while there are huge lows, he finally comes out on top, before being rushed to hospital after clutching his chest.
Win It All is a great film out of the many films about gambling in that it shows how temptation regularly gets the better of people in everyday life. We also see how even when the chips are down so to speak, even when there seems to be no hope left, there’s always a chance to turn things around. In this case Eddie seemingly lost everything and looked like he would have to leave town but that last game of poker managed to be the turning point, even though the odds were heavily stacked against him.