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By Root 1190 0

gym of the Gate of Heaven Church. The brick church was built in 1863 during a period when the Irish immigrant population was exploding and spreading east across Southie toward City Point. Kenny practically lived in the hall, playing basketball year after year in the church’s Catholic Youth Organization, or CYO, league. He was ten years old when a young priest named Father Kevin Toomey came to Gate of Heaven. Father Toomey ran the CYO programs, and he became a mentor to Kenny and his friends who hung out at “Gatie.” Father Toomey drove the boys to their away basketball games. For a couple of years when Kenny, Mike Doyle, Brendan Flynn, and Bobby McGrail were teenagers, they picked up $10 each from the father for “breaking down the hall” after Bingo Night and getting it ready for Saturday CYO basketball. The boys worked late, and Father Toomey often came by to check on them. He would sometimes toss around a football to break up the monotony of folding tables and chairs at midnight. “He kept us straight,” Kenny said. When Kenny was a high school senior in 1987, he was awarded the parish’s Catholic Youth of the Year Award, and a plaque inscribed with his name was hung in the Gatie gym. The winner the year before was his best friend, Mike Doyle.

Kenny had everything he wanted within a five-minute walk from his house—his friends, school, church, the Gatie gym, the playing field at the corner of H and Fifth Streets, and the Italian cold-cut grinders at Mike Caputo’s parents’ variety store. His boyhood was simultaneously unexciting and fulfilling. “I just did what I was supposed to do,” he said. His horizon expanded a bit when he and his friends got their drivers’ licenses. “We’d drive to Castle Island to Sully’s,” he said, “which has the best hot dogs in the world.” It was a comment at once serious and comic. Castle Island in Boston Harbor, just off City Point, was connected to Southie by a causeway. In 1970, when Kenny was two years old, the island and the fort built on it during Colonial times were placed on the National Register of Historic Places. It was only about a mile from Kenny’s house. But to a boy on H Street, the five-minute drive there seemed really far away.

It wasn’t as if Kenny never left Southie. In the summers, his mom took him and his sisters to the Cape. They’d pile into the station wagon and visit Peg O’Brien at her cottage, nicknamed “Grump’s Stump.” They often went on weekend and vacation trips with their mother’s friends—Peg, Twinkie, Nancy, and Arlene. The kids swam and played while the mothers enjoyed “mothers’ medicine,” frozen lime juice and vodka.

The Conleys traveled to Disney World in Orlando, Florida, when Kenny and Kris were eight years old, and they drove another time to Niagara Falls, where they splurged and stayed at a Sheraton hotel. During summers they sometimes drove seventy miles north to York Beach, Maine, and stayed at the Sands Motel with its large swimming pool. During school vacations, families assembled at spots like The Elms, a ski resort in Manchester, New Hampshire, or the Brickyard, another skiing area in New Hampshire, where Kenny broke his leg when he was twelve.

The one dark shadow was his father’s drinking. “It was never really a problem at home or on vacations,” Kris said. “But if my parents argued it was about Dad’s drinking and his being out and carrying on.” Kenny’s father had a rough-and-tumble look about him; he was a heavy smoker with tattoos on his forearm; later, he shaved his head and had an earring in one ear. After working all day driving trucks he would hang out in the bars. “You knew when he was drinking, but he was never doing it around the house,” Kris said. Their mother wouldn’t let him. Over time, the tensions got the better of the couple. The marriage broke down for good soon after Kenny and Kris graduated from high school. Maureen and Ken never divorced, but they never lived together again. And it was during this troubled time that Maureen started drinking heavily. “I knew it was a problem when I saw her drinking at home,” Kris said. She saw it as her