an ode to his friends and their place inside the closet door in his bedroom. It read: “H + Fifth…#1.” Under that, Kenny then drew a shamrockand wrote “Southie” underneath the shamrock, and then he wrote his friends’ names.
Sports were king. Kenny and his friends played wiffleball, baseball, pickup football, just about any game they could come up with. Lots of kids in Southie laced up ice skates and became hockey players at the neighborhood rink, but Kenny never caught the hockey bug. Right away, his favorite game was basketball. He was always tall for his age, an advantage Kenny had right into adulthood, when he topped six feet and kept going.
But his height did not necessarily mean Kenny was the hot player everyone wanted when it came to choosing up sides. “I wasn’t usually the first pick,” he said. Kenny was not what was called a “skill player.” He wasn’t a fancy passer or ball handler whose slick moves faked and fooled players on the other team. He didn’t possess a sweet shot, either beneath the hoop or from far away. Kenny was the opposite of finesse. “My game?” he once asked rhetorically. “I don’t got game.” He joked: “I’m not known for anything except for standing there.” His game was physical, rugged, and without nuance. He pulled down rebounds. In fact, his game mirrored his personality—straight-ahead and no bull. There was never anything slick about Kenny Conley. On and off the court, what you saw was what you got—a hardworking, unpretentious kid without a shred of guile.
Kenny played most of his basketball one block away from his house in the second-floor 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.