John DeCarli’s review published on Letterboxd:
I like most of Swanberg's films as I'm watching them, but even in the best cases they start to evaporate from scene to scene. This is unfair because the guy's an indefatigable artist and I just sit around and watch movies, but: why should I care about a story like this if he doesn't? I don't feel a great deal of touch or sensitivity to this character study that yo-yos its protagonist on a whims and only uses the ping-ponging emotions of an addiction drama until it becomes convenient to drop it completely. In fact, Win It All would have been better off dropping that manipulative structure sooner, because a lot of the budding romance and the mixture of pride and concern of his brother (always love Joe Lo Truglio) are sweet and endearing. A mixed bag, like Digging for Fire.