the aging crime boss from Southie had hit the road at the beginning of the month after a corrupt FBI agent tipped him off to a pending federal indictment. Whitey disappeared with a girlfriend, and soon enough the sixty-six-year-old killer made the FBI’s Ten Most Wanted List alongside Osama bin Laden.
Whitey was the talk of the town, especially in Southie. But for twenty-six-year-old Kenny Conley, another son of Southie, all the Whitey talk was background noise to personal anguish. His mother had died—on Thanksgiving Day. She’d fallen ill suddenly in October, was hospitalized, and fell into a coma. She never recovered. She was fifty-two.
“I took that hard,” Kenny said. He and his mother had been very close. “It was the toughest thing I ever went through.” He thought about his mother every day. But he was not about to talk to Bobby Dwan about her. “When I’m on the job, I focus on the job.”
The first-time partners left the D–4 station after midnight. Within minutes, the Delta K–1 unit was heading to East Newton Street in the South End to investigate a report that prostitutes were working a street corner despite the sub-freezing cold.
Growing up in South Boston, Kenneth Michael Conley always wanted to be a cop. His uncle Russ—his father’s oldest brother—was on the force and worked for years at the same station where Kenny was eventually assigned—Area D–4. As a boy, he had been impressed by his uncle’s uniform. “I’d see my uncle coming home, in his uniform with his partners, coming to see my father, and it excited me.” In addition, Kenny’s boyhood perspective on his uncle’s duties neatly fit with the Southie virtue of help thy neighbor. “I like to help people,” he said. To a question in his eighth-grade yearbook asking what he would be doing twenty years later, Kenny’s answer was: “Boston Police Officer.”
His modest upbringing was one of the typical Southie stories unfolding within a few blocks of home. When he and his twin sister, Kristine, were born on December 11, 1968, his parents lived in a third-floor walk-up at 599 East Fourth Street with their first-born, Cheryl. His parents, Ken and Maureen, or “Moesie,” were both from Southie. They’d met when their respective “crowds” crossed paths. Maureen; her oldest friend, Peg O’Brien; and their other friends hung out at Frank and Rosie’s on N and Sixth Street. Kenny and his pals hung out at a spa one block away, on N and Fifth. Maureen and the girls would go to the spa for pizza and to play the jukebox, and the guys in Ken’s crowd would follow them back to Frank and Rosie’s. “Before long it was one crowd,” said Peg O’Brien. Ken, who was four years older than Maureen and a high-school dropout, worked as a truck driver and later as a track worker for the Massachusetts Bay Transportation Authority, or “the T.” Maureen worked for an insurance company, but quit when Cheryl was born. Within a couple of years, though, Maureen and Peg got part-time jobs at Gillette, headquartered in Southie, testing new deodorants. They’d sit with a “panel” of other women in hot rooms with pads under their sweating armpits to test the effectiveness of the deodorant. The two friends worked as a tag team, alternating between work and home. While Maureen worked, Peg watched Cheryl; when Peg worked, Maureen watched Peg’s daughter.
“Kind of like Lucy and Ethel,” Peg O’Brien said. “I think it was for about ninety minutes a day. We got paid about $35 a week.”When the twins Kenny and Kris were born, Maureen decided to stop working again and stay at home with her three kids.
The Conleys lived in a four-bedroom apartment with a single bathroom, one block from East Broadway, which, along with West Broadway, was Southie’s main commercial street. The two Broadways ran the length of Southie, from Boston Harbor on the east to a bridge on the west side that connected the neighborhood to the city. For a
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