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 anothertime 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 mother’s “mid-life crisis.” “She was always a doer, but now she had no kids to tend to, she was upset about the marriage, she had this freedom and was unhappy.”
Maureen had been working for some time as a waitress at the Park Plaza Hotel. She’d gone back to work when the twins were in the fifth grade. Having taken her role as a stay-at-home mother so seriously, she actually asked the eleven-year-old twins Kenny and Kris for their permission. “She explained we would only be home alone for about thirty to forty-five minutes between the time we got home from school and when she got home from work,” Kris said. “She was all concerned, but we thought it was great.” They’d go wild during the brief but daily stay of parenting. “We’d have these blow-out fights,” Kris said. But the shenanigans ceased once they heard their mom pushing open the big front door.
When it came to school, Kenny Conley—along with Mike Cox in Roxbury and Smut Brown in Mattapan—was a child of busing, the court-ordered remedy to desegregate Boston’s public school system. None of the three boys was ever directly in the line of fire. Their parents joined the legions of Boston parents who, during the busing era, avoided the tumultuous public schools and sent their kids elsewhere. Mike Cox was sent to St. Mary’s School in the neighboring city of Brookline, Smut Brown was enrolled in the METCO program and bused to the affluent Boston suburb of Wellesley, and Kenny Conley attended one of the Catholic parochial schools not far from home.
Kenny considered himself a “Gatie,” and the Gate of Heaven School was right around the corner, but he and his sister attended elementary school at St. Peter’s. The brick Catholic parish school with the tiny asphalt playground was located on Sixth Street, a “commute” of three blocks from Kenny’s house. He attended St. Peter’s because Cheryl had gone there and his parents liked it. The school was grades one to eight. Kenny’s classmates were the same year after year—another stitch in Southie’s tight-knit way of life. “Each grade was about thirty-five kids, and I basically went