samarthbhaskar’s review published on Letterboxd :
Joe Swanberg and Jake Johnson are getting a lot of at-bats with these short, almost-movies they keep making. And they're getting better too. Movies like Digging for Fire, Drinking Buddies, and Netflix's anthology series EASY, are coming together to form something of an oeuvre. I don't think there's enough, yet, to come up with a philosophy of Swanberg's film making, but over time, that's something that could come together.
In Win It All, we have a movie that's not quite as developed as Drinking Buddies or Digging for Fire but has more going on than a single episode of EASY. Chicago, especially the north side, are beautifully characterized through bars, streets, neighborhoods, houses and people. If we did come up with a theory of Swanberg, Chicago or the Midwest at least, would have to play a big role in it.
Swanberg and Johnson rightly stayed away from investing too much of their story's drama in the card playing. It's hard to telegraph the drama and stakes of a card game to people who aren't playing the game. Films like Rounders probably pulled that as well as can be done in recent memory.