Jack Mosley (BRUCE WILLIS) is a burned out New York City cop with a drinking problem and overall tired attitude about his job and life. Accordingly, he's not thrilled to learn he must transport petty criminal Eddie Bunker (MOS DEF) from the local lockup to the courthouse sixteen blocks away. Along the way, however, he learns that someone wants Eddie dead as he thwarts an attempt on the criminal's life.
Taking refuge in a nearby establishment, Jack learns what's really occurring when his former partner of twenty years, Frank Nugent (DAVID MORSE), arrives with a handful of other cops. It seems that Eddie is a key witness set to testify against a number of bad cops, and Frank says they can't allow that to happen.
But when Frank tells Jack to go home and it seems the cops are going to execute Eddie right there, the hung-over cop with a bad leg takes matters into his own hands. Shooting one bad cop in the leg and holding a shotgun on Frank, he gets Eddie and the two manage to escape. Back on the streets and facing a deadline of getting the witness to the courthouse by 10:00, Jack does what he can to traverse those sixteen blocks, all while Frank and a growing number of cops try to stop him.