The school was old and prestigious, a real coup for the kid from Roslindale. But from the moment John Connolly crossed the threshold of Roxbury Latin, he struggled.
Suddenly, his essays were expected to be top-notch, hours of homework were given, and his classmates from the suburbs seemed to know everything.
He had wanted to go to Boston Latin, where many of his neighborhood friends were headed. But his parents were adamant: Roxbury Latin it would be.
Every Roxbury Latin boy is expected to play sports, and Johnny — his family still calls him that — quarterbacked the football team for two years. He’d come home, books piled high, so exhausted from football that it was a battle to make it up the hill to the house on Cerdan Avenue.
“He broke down and cried and cried and cried,” says his father, Michael. “He said, ‘I can’t do it.’ ”
Eventually, he’d come to love the school, but it took a good two years — and many tears. “I was very scared to go there,” Connolly says.
Nearly three decades later, the memories remain vivid. Still, he knows his struggles in that period pale in comparison with the childhood ordeals of many others, and he chuckles when asked if there was anything — anything at all — out of the ordinary about his early years.
“I had a very traumatic childhood,” he deadpans. “We moved three times by the time I was 7.”
Pause. “All within five blocks of each other.”
Connolly, now 40 and a finalist in Boston’s mayoral race, was the oldest of four kids born into a tightknit family in a Roslindale neighborhood where life revolved around sports, church, and family.
“It was a wonderful place to raise kids,” says Lynda Connolly, their mother. “The kids knew the adults, the adults knew the kids, and the families knew one another.”
The Connolly kids were also steeped in politics. John was an infant when his father was elected a state representative and 5 when he was elected Secretary of State for the Commonwealth, a position he held for 16 years.
His mother, a lawyer who worked from home when the kids were young, would later have her own career in public life: she retired this year as chief justice of the Massachusetts District Court, after being appointed an associate justice by Governor Weld in 1997.
Public service was a given in the Connolly family. When he applied to college, the teenaged John wrote: “I hope to be a public servant. I have been given so much. I hope to have an opportunity in my work to give something to those who have nothing.”
The house John loved the most was at 122 Montclair Ave., where his grandmother also grew up. It was the family’s second Roslindale home. When he was born on July 6, 1973, his parents lived on the second floor of a three-family.
Lynda and Michael Connolly married at the end of her first year of law school, and she had John during her third year. Within six years, there were four little Connollys, including Justin, now 38, and identical twins Lauren and Allison, 34.
Though being the oldest had it privileges — John called the top bunk in the room he shared with Justin — it also had its drawbacks.
“I think as the oldest, you tend to be pushed into things that could be embarrassing,” says Justin, who is senior vice president for college networks at ESPN in Bristol, Conn. “Whether it be playing the trumpet, which is something my mother insisted he do, or joining the Cub Scouts or being the first in the family to play organized sports. In each instance, the oldest becomes the test case and not necessarily based on their own interests and desires.”
Johnny Connolly found both a faithful and fickle audience in his younger siblings. “We never pulled any punches when it came to mocking him, but he was a really good sport about it,” says Justin. “At the same time, he’d have no problem giving it back to us.”
John always called himself the “experimental child” and his mother believes that being firstborn played a big role in who he became. “I think because he was the oldest, there was an expectation that he had to set an example, and he stepped into that role very naturally,” she says.
Because of the closeness the siblings shared, Justin believes they have all tried to replicate the family pattern in their own marriages, with the four of them each having young children close in age. “I have 11 grandchildren, and the oldest is 5,” is the way Lynda Connolly puts it.
The family dinner table was more their mother’s turf since their father was away some nights. “The house was always a busy, active environment, and I figured out my role was to keep busy and active from spilling over into pure, unadulterated chaos,” Lynda says. “Sometimes I succeeded and sometimes not.”
A colorful character on Beacon Hill, Michael Connolly earned the moniker “Secretary of Space” for his eccentricities as well as his prescient interest in the threat to the ozone layer. But he also earned respect for a well-run office that pursued corporate securities regulations, forced some large settlements for consumers, and diligently enforced the open-meeting law.
His son remembers him as his math tutor, his football and baseball coach and the one who would take him to football games at his beloved alma mater, Holy Cross. “We’re very close but our relationship has never been about politics,” says John, who describes his dad as “a free spirit . . . a dreamer in the best sense of the word.”
Their father took the breakfast shift. The kids weren’t allowed to leave the house without first eating half a grapefruit and a bowl of Cheerios, says Lauren Connolly Nussbaum, who lives in New Canaan, Conn., and does fund-raising for nonprofit groups. “Our friends made fun of us, but our father was big on a good breakfast.”
No TV was allowed on school nights. But it wasn’t for educational reasons, reveals their mother. “You know where that came from?” she asks. “I just couldn’t handle another voice in the room with all these little kids.”
In the mornings, John would walk to Holy Name with friends, picking up more at each corner. The family attended Mass each Sunday, where he was an altar boy.
“Roslindale was a great mix,” he says. “There were electricians and insurance salesmen, city workers and state workers, and lots of families.”
But there were also difficult issues. “In the city of Boston in the ’70s’ and ’80s hatred was palpable, on race lines, and that stuff stays with you,” says Connolly. “You’d hear terrible things on the street. They were very few voices, but very loud.”
Roslindale today is a different neighborhood than the one where he grew up. At the recent Roslindale Day Parade, Connolly’s route took him past the trendy Birch Street Bistro, Threads Boutique, and the Select Cafe. “They didn’t used to call it the ‘Village’ then,” he said. “It was the square, and my mother wouldn’t let me go there after dark.”
Young Johnny was a good, but not perfect, kid. “He came from a long line of imperfect people,” says his mother, laughing.
But the missteps were minor.
In the first grade, miffed at his mom, he threatened to run away from home. “Don’t forget your toothbrush,” she told him. So he put it in his backpack and walked down the hill, but once there, realized he wasn’t allowed to cross Weld Street. So he sat on the curb for a while before returning home.
When he was 3, he escaped from the pew at the crowded 9 a.m. Mass at Holy Name. “He runs up to the altar, hooks a right, and I’m out of the pew trying to figure out where to nail him,” says his father. “And he starts running in the other direction. And then it becomes a scene. People thought it was a riot.”
In the first grade, he threw rocks at a car. “My dad marched me up and made me apologize,” he says. Another time, he “mouthed off” to a teacher at Holy Name, and had to write a letter of apology.
Lynda Connolly stayed home until the twins were in the fifth grade, working some nights teaching law and then running a small practice from home. She’d grown up in Alexandria, Va., with parents who were Massachusetts natives, big Kennedy supporters and civil rights advocates.
After graduating from the College of William & Mary, she worked her way through Boston College Law School.
“My parents instilled in us that they would educate us through college, and then we were on our own for graduate school,” says Lynda, now director of the pre-law program at Simmons College.
That was also the deal with her own children, who had to buy their own sneakers and books, too. John was a caddy and busboy and a vendor at Fenway Park for six years.
He’s still paying off student loans: “I’m going to pay forever.”
When he was in the sixth grade, his parents handed him an application to Roxbury Latin, the country’s oldest continuously operating school, founded in 1645.
He was a big kid, and in high school, played both receiver and safety on the football team and forward on the basketball team. “He was a very good but not a great athlete,” says retired headmaster Tony Jarvis, who now teaches at the Yale Divinity School.
But he was a gifted debater, captain of the team, and president of the school’s Model United Nations Club. “He won more trophies than anyone had won,” says Jarvis. “As a junior, he won the North American public speaking championship.”
But when he went to England for a competition, Connolly recalls, “I got my hat handed to me.”
Jarvis, who was headmaster for 30 years, describes the young Connolly as “kind, open to everyone, tender and, I can even say, sweet. It sounds sappy, but he was truly a great kid, and not just in my view.”
Jim Hamilton played football and basketball with Connolly at Roxbury Latin, and describes him as an avid athlete, a solid student and an easy-going guy. “Whether from Wellesley or West Roxbury, he had a comfort with all different kinds of kids” says Hamilton, who grew up in Hyde Park.
Connolly graduated in a class of 48 students in 1991, with an A-minus average and, he says, average SAT scores. “I was known more for working extraordinarily hard than being academically talented.”
He applied early to Georgetown University’s foreign service school but was rejected. He then applied to Harvard, where his maternal grandfather had gone for a year before dropping out.
At Harvard, John was assigned in the housing lottery to Currier House, a nondescript building half a mile north of Harvard Square, far from the coveted ivy-covered houses overlooking the Charles River.
“Currier was known as the place where those who had high lottery numbers went,” says Peter Fitzgibbons, who roomed with Connolly for three years. “We rode our bikes to campus, even in winter.”
Fitzgibbons remembers Connolly as a gregarious but messy guy. Like others, he mentions Connolly’s sense of humor, but like others, he’s hard-pressed to give examples. He does recall the time when a friend invited them to his family’s home on Cape Cod. “John got out of the car wearing a Robin costume, with tights, the tight shirt, cape, mask, everything,” says Fitzgibbons, an orthopedic surgeon. “It was totally random, and he wore it all night.”
After the rigors of Roxbury Latin, Harvard didn’t seem as tough to Connolly, and he graduated cum laude. But he does regret one thing. His major: government.
“What do you learn in a government major?” he asks. “I wish I’d studied history and literature and really dug into liberal arts.”
But even from his early years, friends believed that politics would be part of his life, says Jim Hamilton, who is associate head at the Brooks School in North Andover. “I ran into another friend of ours recently and he joked that in high school, we all wanted to play for the Patriots, and John wanted to be mayor.”
Bella English can be reached at email@example.com.