Somewhere in Cleveland, not long ago, Cosimo (LUIS GUZMAN) and Toto (MICHAEL JETER) are two petty thieves trying to steal a car. Cosimo is caught and ends up in prison where his lifer cellmate tells him about a terrific heist opportunity. It seems that the man was the bricklayer who helped refurbish the old flour factory building into a jewelry store and apartment.
Needing to get out to take the job, Cosimo doesn't his girlfriend, Rosalind (PATRICIA CLARKSON), the details, but does want her to find a patsy who will take the fall for the grand theft auto case. She goes to see the nebbish Toto who then goes to see Basil (ANDREW DAVOLI). He doesn't want to do it, even for $15,000, but says they should see Leon (ISAIAH WASHINGTON) who may know of someone who could use the money in exchange for the time.
He can't since his sister, Michelle (GABRIELLE UNION), is getting married, but suggests that they see Riley (WILLIAM H. MACY). He's a former photographer who's now raising his infant son by himself while his wife is in prison, but he believes that boxer Pero (SAM ROCKWELL) might be their man.
After losing his latest bout, Pero agrees but is so bad at taking the rap that Cosimo gets more time added to his sentence. Thinking Pero's stuck there with him, Cosimo informs him of the details and Pero thanks him as he leaves on probation. The rest of the gang then forces the details of the job from him, and soon they bring in Jerzy (GEORGE CLOONEY), a wheelchair-bound safecracking whiz who now teaches others the tricks of the trade.
Meanwhile, Pero starts seeing Carmela (JENNIFER ESPOSITO), the bewitching maid who works for the elderly ladies who've now moved into what was the vacant apartment and entry point into the jewelry store. As more complications arise, including the presence of Detective Babitch (DAVID WARSHOFSKY), the bumbling thieves try to pull off their heist and dream of what they'll do with the reported $300,000 in the store's safe.