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PART ONE

The Prince of Darkness is a gentleman

WILLIAM SHAKESPEARE (ACT III, SCENE 4),

KING LEAR

CHAPTER ONE

1975

Under a harvest ent John Connolly eased his beat-up Ply Wollaston Beach Behind him the water stirred and, further off, the Boston skyline sparkled The ship-building city of Quincy, bordering Boston to the south, was a perfect location for the kind ofthe beach, Quincy Shore Drive, ran right into the Southeast Expressway Heading north, any of the expressway’s next few exits led shborhood where Connolly and his “contact” had both grown up Using these roads, the drive to and from Southie took just a few minutes But convenience alone was not the main reason the location made a lot of sense Most of all, neither Connolly nor the ether in the old neighborhood

Backing the Ply the beach, Connolly settled in and began his wait In the years to co would never stray too far fro within a radius of a ators and gangsters

But that ca Wollaston Beach, the thru to the buzz inside the car that was like an electric charge Having won a transfer back to his hometown a year earlier, he was poised to make his mark in the Boston office of the nation’s elite law enforceoing to be his chance His big moment in the FBI had arrived

The nervy agent was co with a rare public relations setback In Congress inquiries into FBI abuses had confirar Hoover had for years been stockpiling inforures in secret files The FBI’saround were sensational disclosures involving a bizarre partnership between the CIA and the Mafia, also unearthed during congressional investigations There was talk of a CIA deal with mafiosi to assassinate Cuba’s Fidel Castro, and of ars

Indeed, it suddenly seemed like the Mafia was everywhere and everyone wanted a piece of theHollywood Francis Ford Coppola’s e audiences when it opened the year before A few months earlier the picture had won a slew of Oscars Connolly’s FBI was now deeply into its own highly publicized assault on La Cosa Nostra (LCN) It was the FBI’s number-one national priority, a war to counter the bad press, and Connolly had a plan, a work-in-progress to advance the cause

Connolly surveyed the beachfront, which at this late hour was e Quincy Shore Drive The bureau wanted the Mafia, and to build cases against the Mafia, agents needed intelligence To get intelligence, agents needed insiders In the FBI the measure of a man was his ability to cultivate informants Connolly, now seven years on the job, knew this much was true, and he was deterent with the right touch His plan? Cut the deal that others in the Boston office had atte to land Whitey Bulger, the elusive, cunning, and extreend in Southie The stylish FBI arriviste wasn’t the type to take the stairs He was an elevator er was the top floor

The bureau had had its eye on Bulger for soent named Dennis Condon had taken a run at him The tould ed to elicit extensive inside infor the city’s underworld—as allied hoh, detailed account of the landscape with an acco lineup of key characters Condon even opened an informant file for Whitey But just as quickly, Whitey went cold They o well In August, reported Condon, Whitey was “still reluctant to furnish info” By September Condon had thrown up his hands “Contacts with captioned individual have been unproductive,” he wrote in his FBI files on Septe closed” Exactly why Whitey ran hot then cold was a ence he’d provided had proved disco Maybe there was a question of trust: why should Whitey Bulger trust Dennis Condon of the FBI? In any event, the Whitey file was closed

Now, in 1975, Condon was on the way out, his eye on his upco, and the younger agent was hungry to reopen the Whitey file After all, Connolly brought soer He’d grown up in a brick tene project in South Boston Whitey was eleven years older than Connolly, but Connolly was oozing with confidence The old neighborhood ties gave him the juice others in the Boston office didn’t have

Then, in an instant, the waiting was over Without any warning, the passenger side door swung open, and into the Plyer Connolly jumped, surprised by the suddenness of the entry, surprised he was caught unaware He, a trained federal agent, had left his car doors unlocked

“What the hell did you do, parachute in?” he asked as the gangster settled into the front seat Connolly had been expecting his visitor to pull up in a car alongside hier explained that he had parked on one of the side streets and then walked along the beach He’d waited until he was sure no one else was around, and then he’d come up behind from the water

Connolly, one of the younger agents on the prestigious Organized Crime Squad, tried to calm himself Whitey, who’d just turned forty-six on Septeer than life, even if he just barely hit five-feet-eight and weighed an ordinary 165 pounds He was hard-bodied and fit, with penetrating blue eyes and that signature blond hair, swept back Under the cover of darkness, the two an to talk, and then Connolly, properly obsequious to a neighborhood elder as also an icon,your friends in law enforcement”

THIS was Connolly’s pitch to Whitey: you need a friend But why?