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 him. Bulger 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 September 3, sat in the front seat, larger 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 men began to talk, and then Connolly, properly obsequious to a neighborhood elder who was also an icon, made his offer: “You should think about using your friends in law enforcement.”
▪ ▪ ▪
This was Connolly’s pitch to Whitey: you need a friend. But why?
In the fall of 1975 life in the city was tumultuous and changing unpredictably. From where they sat along the vacant beach, the two men could see the Boston skyline across the water. At the time the unexpected good fortunes of their Red Sox electrified the citizens of Boston. Yaz, Luis Tiant, Bill Lee, Carlton Fisk, Jim Rice, and Fred Lynn—who, after the season, would be honored as both the rookie of the year and the American League’s most valuable player—were in the midst of a glorious run for the World Series title against the powerful Cincinnati Reds.
But closer to home the world was dark and unstable.
The nightmare of busing had begun its second year. In 1974 a federal court order to bus black students from Roxbury to South Boston High School in order to achieve racial balance in the city’s segregated public schools had turned the neighborhood into a war zone. The rest of the country tuned in, and people were getting to know Southie through televised images and front-page newspaper photographs featuring riot police, state troopers patrolling school corridors, rooftop police snipers, and legions of blacks and whites screaming racist chants at one another. The Pulitzer Prize in photography was awarded for a jaw-dropping 1976 picture of a black man being rammed with an American flag during a disturbance outside of city hall. Nationwide the neighborhood was seen through a prism of broken glass—a bloodied first impression that was searing and horrific.
Whitey’s younger brother Billy was in the middle of it all. Like all the neighborhood’s political leaders, Billy Bulger, a state senator, was an implacable foe of the court-ordered busing. He never challenged the court’s findings that the city’s schools were egregiously segregated. He did, however, strongly oppose any remedy that forced students to travel out of their home school districts. He’d gone to Washington, DC, to complain and present their case to the state’s congressional delegation, and once there, he delivered a speech to a group of antibusing parents in the pouring rain. He hated the view outsiders were getting of his neighborhood, and he denounced the “unremitting, calculated, unconscionable portrayal of each of us, in local and national press, radio and television, as unreconstructed racists.” To him the issue was his neighbors’ legitimate worry for the welfare and education of their children. Back home Billy Bulger spoke out regularly against the unwanted federal intervention.
But busing would not go away, and the summer that had just ended had not gone well. In July six young black men had driven to Carson Beach in South Boston and ended up in a fight with a gang of white youth that left one black hospitalized. In his younger days John Connolly had been a lifeguard along the beaches of South Boston, just as Billy Bulger had been before him, and now the sandy beaches had become another battleground. On a Sunday in August police helicopters circled over Carson Beach and Coast Guard boats patrolled offshore while more than one thousand black citizens drove to the beach in a motorcade of several hundred cars. They were accompanied on their “wade-in” to the beach by more than eight hundred uniformed police officers. The cameras rolled.
By the time Connolly had arranged to meet Whitey along Wollaston Beach, the schools had reopened. Student boycotts and fights between blacks and whites were regular events. Thinking it might help ease the racial tension, officials for the first time tried to integrate the football team at South Boston High School. But the four black players who reported to the first practice had to do so under police protection.
The neighborhood was torn apart, and Connolly knew that, could feel that pain, because it was his neighborhood as well, and he had played off this bond in lining up his meeting with Bulger. But although the bond might have gotten him an audience with Whitey, he now had to pitch a deal to his boyhood hero. Connolly most of all wanted to exploit the wider underworld troubles brewing between the Boston Mafia and a gang Bulger had signed on with in neighboring Somerville. Bulger, in charge now of the rackets in Southie, had hooked on with the Somerville crime boss Howie Winter. The gang operated out of a garage in the Winter Hill section of the small city just across the Charles River to the west. In the past year Whitey had paired off with another member of the gang, Stevie “The Rifleman” Flemmi. They got along, found they had certain things in common, and had begun to hang out.
By the time Connolly and Bulger met, the young FBI agent had done his homework. He knew Bulger and the Winter Hill gang were facing a two-pronged threat from a local Mafia that for decades was controlled by the powerful underboss Gennaro J. Angiulo and his four brothers. Pending at that moment was a dispute between the two organizations over the placement of vending machines throughout the region. There had been wiseguy bluster about shootouts as a way to settle the matter. With all this instability, Connolly argued, a wiseguy could use a friend.
Besides, Angiulo was wily and inscrutable. He had a knack for setting up for arrest those he no longer had any use for. For example, a few years earlier a mob enforcer had veered out of his control. Angiulo, the story went, had reached out to his contacts inside the Boston Police Department, and the mob renegade was soon picked up on phony gun charges after crooked cops planted weapons in his car. No one knew for certain whether Angiulo in fact had the kind of access to manipulate an arrest like that. But this was the story making the rounds, and Whitey Bulger and the rest of Howie Winter’s gang believed it. As Connolly well knew, perception was all that actually mattered.
Bulger was clearly concerned about Angiulo setting him up. “What if three cops stop me at night and say there was a machine gun in my car?,” Whitey had complained. “Who is the judge gonna believe? Me or the three cops?” Connolly had positioned himself to play off such crosscurrents of underworld paranoia.
The two men sat in the Plymouth, the city lights rippling on the water. “You should use your friends,” Connolly stressed—a line that caused Bulger to consider the agent intently, sensing an opening for the upper hand.
“Who?,” Whitey asked at last. “You?”
“Yeah,” replied Connolly to a ruthless man who used up people and threw them away. “Me.”
▪ ▪ ▪
Connolly’s proposal was simple: inform on La Cosa Nostra and let the FBI do the rest. Bulger knew, Connolly recalled, “that if we were chewing on the Mafia, it was very difficult for the Mafia to be chewing on them.”
In fact, the moment Connolly had indicated he wanted a meeting Bulger knew what the FBI wanted. For weeks Bulger had already been working the proposition over in his mind, weighing the pros and cons, figuring the angles and potential benefits. He’d even gone and consulted with Stevie Flemmi. Bulger brought up the subject one day when the two of them were in Somerville at Marshall Motors, the auto repair shop Howie Winter owned. The one-story garage was a faceless building made of cinder blocks. It resembled a concrete bunker and served as a business front for the gang’s wide-ranging illegal enterprises, which since 1973 had expanded to include fixing horse races up and down the East Coast.
Bulger told Flemmi that the FBI agent John Connolly was making a bid for his services. “What do you think?” Bulger asked Flemmi when the two were alone. “Should I meet him?”
The question hung