Jay Davidovich, a big, burly, blond Jew, is an insurance company apparatchik whose job is to prevent losses that Trans/Oxana has insured against. Kent Trowbridge is a handsome Hollywood actor who just received his second DUI while playing bumper cars in his Ferrari with two palm trees and a median. New Paradigm Studios holds an eight-figure Trans/Oxana policy insuring fulfillment of his contract as a major performing artist. But now Kent will be doing prison time, and with no director yelling "Cut!" when things get dicey on the inside, Jay decides Kent needs a jail coach. Enter Katrina Thompson, whose past includes jail time, a stint in the Marines, a daughter, and a hustler named Stan. The first will help Jay, the second will impress him, the third will charm him, and the fourth will almost kill him--but that's life in the loss-prevention business.