Tenth in a series of profiles of Boston’s 12 mayoral candidates.
The dashboard clock reads 7:44 a.m. as John Connolly carefully straps Teddy, just shy of his fourth birthday, into the back seat of the family’s dark gray minivan. First stop, the Parkway School, a two-story preschool with a half-dozen “John Connolly for Mayor” signs on the front gate.
Then it is back home, where he helps his wife, Meg, corral the rest of the Connolly crew in the van, including newborn MaryKate, who has miraculously slept through the morning’s tumult, and their very excited 5-year-old, Clare, purple lunchbox in hand.
For a man who has gone to great lengths to carve out a profile as the race’s “education candidate,” the morning’s task is as symbolic as it is personally important: It is the first day of school.
“Wait, wait,” Clare calls out, reaching back into the house to grab a second campaign sticker for her lunchbox before they all drive to the Trotter School in Dorchester for the start of kindergarten.
Connolly’s ideas for shaking up the city’s schools are central to his bid for office, the reason he entered the race, the reason his supporters love him, the reason his detractors despise him.
His speeches include passionate appeals to improve school quality, his television commercials chronicle his fight to rid school cafeterias of expired food, and many of his endorsements have been announced on elementary school steps.
The 40-year-old councilman even held his February campaign launch, which came well before Mayor Thomas M. Menino announced he would not seek reelection, at a school, speaking just feet from Brighton High School.
Time and time again, Connolly has stressed that schools are the key to ensuring that Boston’s children can grow up, be educated, and come back to raise their families in the city, as he did.
Born and raised in Roslindale, Connolly reminisced earlier this week about old storefronts and high school hangouts as he walked through the neighborhood that his father, Michael, spent five years representing in the State House.
“It’s a really different city than the one I grew up in,” he said. “But I really like something about that. It’s infused with new energy and new vitality and new people.”
After graduating from Roxbury Latin, Connolly did his undergraduate studies at Harvard College and then spent three years teaching middle school at the Nativity Mission School on the Lower East Side of Manhattan. After returning to Boston, he spent another year teaching sixth grade at Boston Renaissance Charter Public School in the Theatre District.
“I was not a great teacher,” Connolly offered in his aw-shucks, self-deprecating style, during a candidates forum in Dorchester earlier this week. “But I was mentored by great teachers while I was still working in the schools, and every child deserves a great teacher.”
Connolly has trumpeted this part of his resume on the campaign trail, earning some snide remarks from detractors who say he overplays the few years he spent in a classroom.
He has spent far longer practicing law. He earned his law degree from Boston College and became a practicing lawyer in 2001.
His family life, from an early age, was entrenched in state politics. Connolly’s father served 16 years as secretary of the Commonwealth, while his mother, Lynda, was chief justice of the state’s district courts for eight years.
But Connolly insists that his ambitions have always focused on city government. His first City Council bid ended in defeat in 2005, but he secured one of the council’s four citywide seats in 2007 and has been reelected twice.
“Nobody believes me, but I don’t have any desire to run for governor or senator or another elected office,” Connolly says. Mayor “would be the dream job for me,” he said. “I love cities, and if I’m not mayor, I’m going to find a way to work in urban policy and schools. It’s been my love for the city driving me.”
While much of his campaign has been linked to improving schools, Connolly also stresses his work on the council on environmental issues and public safety.
He often insists that “City Hall should run like the Apple Store,” which is his lead-in to talking about improving city services through new technology and efficiency.
But it is his tenure atop the council’s Education Committee — marked by high-profile clashes with Menino, the Boston public schools brass, and the Teachers Union — that both supporters and opponents most often point to as the defining bullet point in his biography.
Connolly was the only council member to vote against the Teachers Union contract last year, refusing to support a contract that did not ensure longer school days.
At the mayoral forum at the Boston Teachers Union earlier this week, Connolly acknowledged that the wound remains fresh.
“I’m John Connolly, and as the only John Connolly supporter in the room,” he said as he began his first remarks of the night.
The joke drew a few chuckles, but the crowd remained hostile, hissing at any mention of Connolly’s vote against their contract or his support for raising the limit on charter schools.
Last summer, Connolly called for the ouster of Superintendent Carol Johnson, a popular figure in parts of Boston’s black community, for her failure to fire a principal who was arrested on assault charges.
Johnson’s defenders railed against Connolly during a rally at Bethel AME Church, using racially charged language to compare him to opponents of court-mandated school integration in the 1970s.
That ill will was resurrected earlier this year when, in August, Connolly won a pledge of $500,000 from Stand for Children, an at-times controversial education reform nonprofit that receives corporate funding. The following day, under fire from mayoral rivals, Connolly said he would ask the group not to spend money on his behalf.
The only candidate to enter the race before Menino withdrew, Connolly has been on the trail almost twice as long as most of his competitors and seems to have used that headstart to hone his pitch.
Walking quickly up the driveway and to the backyard of a West Roxbury home last Sunday, Connolly nudged up the knot of his orange tie and rolled up his cuffs.
Arriving a few minutes late to this neighborhood meet-and-greet — the 90th such event he has attended since May and the first of three on this day — Connolly immediately worked the circle of residents seated in wooden chairs.
“If someone only has the easy superficial answers, that tells me that they aren’t ready,” said Rachel Poliner, a former social studies teacher, who hosted the West Roxbury event.
Before long, the candidate had delved into his most often used campaign speech, in which he comfortably weaves from discussing schools to housing to poverty and then, of course, back to schools.
He harkens back to the Trotter Elementary School, which was granted turnaround status in 2009, leading to new state money and more control over staffing.
Once considered one of the city’s worst schools, the Trotter has seen marked improvement since being granted autonomy. On Monday morning, students were eagerly heading to the front doors when the Connolly clan pulled up.
The Connollys had just begun the elaborate process of unloading MaryKate’s stroller when Clare took off, dashing gleefully into the arms of her best friend.
As the two girls ran toward the schoolhouse gate, Clare suddenly stopped and grabbed her classmate’s hand.
In a child’s act of generosity, Clare peeled a sticker from her lunchbox and handed it to her friend. Then the two continued toward the building, their lunchboxes now both proclaiming “Connolly for Mayor.”Wesley Lowery can be reached at email@example.com. Follow him on Twitter @WesleyLowery.