"Perfect Strangers," by Tilia Klebenov Jacobs, in When A Stranger Comes To Town, edited by Michael Koryta, Hanover Square Press, 2021.
Gershom is finishing his second prison term for armed robbery when his cellmate Dougal points out the new gold mine: marijuana dispensaries. Cash-rich and security-poor, they are a robber's dream. So when he gets out Gershom begins to plan an elaborate robbery, because he does not intend to go down a third time...
The writing here is very witty. "Five years [in prison] went by like a snail with a hangover." "If this went sideways, they'd lock me up and melt down the warden." And so on.
If you have read a few hundred stories like this you know something will go sideways, But Jacobs found a clever and unexpected way to do that.