Pennsylvania, 1956. Frank Sheeran, a war veteran of Irish origin who works as a truck driver, accidentally meets mobster Russell Bufalino. Once Frank becomes his trusted man, Bufalino sends him to Chicago with the task of helping Jimmy Hoffa, a powerful union leader related to organized crime, with whom Frank will maintain a close friendship for nearly twenty years.
To take down South Boston's Irish Mafia, the police send in one of their own to infiltrate the underworld, not realizing the syndicate has done likewise. While an undercover cop curries favor with the mob kingpin, a career criminal rises through the police ranks. But both sides soon discover there's a mole among them.
Wayne Dobie is a shy cop whose low-key demeanor has earned him the affectionate nickname "Mad Dog." After Mad Dog saves the life of Frank Milo, a crime boss and aspiring stand-up comedian, he's offered the company of an attractive young waitress named Glory for a week. At first both are uneasy about the arrangement, but they eventually fall in love. However, the situation becomes complicated when Milo demands Glory back.
A photographer (Katherine) is asked to spy on a crook who runs an illegal casino and is arranging an auction of a precious pearl.
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