The screenplay is by Charlie Huston, who adapted his own novel, which seems to be a contemporary take on the formula Dave Goodis used for his paperback originals. It would follow a loser who used to be a big shot before a bad decision ruined their career. These losers would get mixed up with a criminal underworld and be forced into participating in nasty goings on. Some classic films have used the Goodis formula to great success, like Shoot The Piano Player and The Salton Sea. However, all that is Goodis is not good, as seen in the directorial misfires Street of No Return and Caught Stealing.
The fact that this time it’s a former promising baseball player is so interchangeable that just makes it feel like the fireman costume was already rented out for another movie. Also, there is no real reason this movie should be set in New York in 1998. Seems like it is just an excuse to recreate the Kim’s Video sign, which, like nearly everything else in the movie, seems to have been done to be cute.

“I just showed up to see Dr. Who in a mohawk and his cat.”
Why aren’t real retro New York novels like War Cry On Avenue C being made into movies? It’s too mean to be a comedy, it isn’t funny enough to be a dark comedy, and it isn’t even as funny as your average action movie. Yet it carries itself like it is the funniest thing off-Broadway, which remains awkward. All the talent is literally wasted, with the best players getting special guest death sequences like the old Police Squad show.
The cracks in Aronofsky’s dam were on full display in the problem-ridden The Whale, but with Caught Stealing, the whole thing breaks open with a wave of poo water. I understand you can’t always hit the ball out of the park each time, but this is exactly the kind of dreck that destroyed the reputations of Altman and Bogdanovich at their career peaks. Aronofsky has a finite amount of time on this earth to make the kind of wonderful movies only he can make, like Requiem For A Dream. Projects like this are time sucking detours for both the creators and the audience. I myself would rather be peeling crabs in the dead of winter without gloves than drag myself through Caught Stealing again. Don’t let this movie steal any of your time.
"…a plodding meander that flagrantly overestimates its appeal."