“Win It All” is spurred forward by Eddie Garrett (Jake Johnson), a degenerate gambler who can’t afford a cup of coffee, being given a duffel bag by an ominous accomplice about to be squired to the slammer. Upon the accomplice’s return, Eddie is guaranteed $10,000. Ah, but what if the duffel bears more than $10,000? The bag, of course, is the narrative bomb and Eddie, frankly, held out longer zipping open that duffel than I would have bet. The bag contains, as it must, swaths of cash, of which Eddie takes a little, gambling it and winning, prompting him to a gamble a little more and lose, gamble a lot more to win back what he lost, lose all of that, etc. That seems tailor made for crazy schemes to get out of the red but “Win It All” mostly remains low key, approaching this crisis pragmatically rather than with all manner of comical complications.
The middle passages, in fact, center on the emergence of a support system for Eddie. Eddie’s brother Ron (Joe Lo Truglio) owns a small business and brings Eddie on as an employee, driving him firmly but lovingly, while Eddie also begins a relationship with Eva (Aislinn Derbez), a less than thought-out character, mostly existing to suggest something to which Eddie can root himself. And while Derbez and Johnson work charmingly enough together they, frankly, have less chemistry than Johnson does with Keegan-Michael Key playing Gene, a fellow gambling addict in recovery who Eddie calls his “sponsor”, a term to which Gene remains resistant in their scenes together where humorous give and take is laced with lots and lots of skittishness. Indeed, in his little time on screen, Key, with a semi-manic don’t-push-me temperament makes clear how precarious the straight life is.
Yet as “Win It All” becomes more concerned with Eddie’s bit-by-bit growth, the more it writes itself into a hole, needing to return to the duffel bag subplot, which theoretically should only add to the urgency but starts to feel more like a plot point that should have been jettisoned on a rewrite. Because as “Win It All” gradually proves itself a movie better without drummed up suspense, when the suspense gets dutifully drummed up, the trap the movie has set for itself is sprung and, sure enough, Eddie, metaphorically speaking, gets caught in a little left field melodrama. It might have been better if he just went up in a puff of smoke.