It's the late 1980s and low-level mobster Giacomo "Jackie Dee" DiNorscio (VIN DIESEL) has just been shot by his junkie cousin Tony Compagna (RAUL ESPARZA). Yet, rather than rat him out, Jackie wants to deal with him the mob way, but gets arrested and then sentenced to thirty years on an unrelated drug bust. Still afraid of reprisals from the extended mob family run by Nick Calabrese (ALEX ROCCO), Tony agrees to be a government witness for district attorney Sean Kierney (LINUS ROACHE) who wants to bring down the entire mob family.
That sets into motion a massive court case where Jackie, Nick and the rest of the mobsters are tried together for various mob crimes in front of presiding judge Sidney Finestein (RON SILVER). Upset that his current lawyer isn't any good, Jackie turns down an offer from lead defense attorney Ben Klandis (PETER DINKLAGE) and decides to represent himself in the case, despite having no legal background or real knowledge of how to proceed.
As the weeks turn into months, the court case evolves into a lengthy affair where Jackie -- who's divorced from ex-wife Bella (ANNABELLA SCIORRA) -- turns the courtroom into something of a three-ring circus, much to the collective dismay of Nick, Ben and especially judge Finestein who repeatedly threatens the charismatic mobster to be cautious about how he proceeds.