Mike Flaherty (Paul Giamatti) is stuck in a rut. He is a volunteer wrestling coach and a failing lawyer. When he happens upon an opportunity to make a little extra money off a client, he takes advantage but finds he has to put the demented man's grandson (Alex Shaffer) on his wrestling team.
When the kid turns out to be a star athlete, Mike thinks he has struck gold, receiving double pay and taking his team to the state wrestling match. However, even though he thinks no one could be the wiser, his scheme rips apart at the seams when everyone closest to him finds out he's a double-crosser.
Also starring Amy Ryan, Bobby Cannavale and Stephen Vigman, Win Win is a story about desperate times not requiring such desperate measures.