Just before Easter in 1995, Harvard senior John R. Connolly went to Manhattan at the urging of his Spanish professor, a Jesuit priest, to visit a boys’ school for low-income immigrant families on the Lower East Side.
By the end of the holiday weekend, Connolly had an offer to teach at the Jesuit-run school, beginning a short career in the classroom that would end three years later in what Connolly tearfully recalls as a “personal failure” at Boston Renaissance Charter School.
Now that narrow slice of his early 20s, his time as a teacher, has become an outsized part of his campaign biography, as the city councilor and experienced corporate lawyer is running to become Boston’s “education mayor.”
“My teaching experience is something that makes me unique in this campaign from day one,” Connolly, 40, said in the first minute of his first televised debate Tuesday night with opponent Martin J. Walsh.
In his political life, Connolly has leaned so heavily on his experience as an educator that he has spawned a grumbling backlash, spread through blogs and social media, that he was never a “real teacher.” He ridicules the criticism as a “birther movement” by disgruntled hard-liners in the Boston Teachers Union who oppose his candidacy.
‘He was the kind of teacher we were looking for.’
“They feed it and then the parents grab it, and then I’m walking down the street and people are asking me why I’m faking my credentials,” Connolly said in an extended interview at a Jamaica Plain restaurant.
He says he learned, in his short teaching career, how to reach students despite stark poverty and broken families in New York. And he described a crushing lesson about how schools can fail, during his trying year at what was then a troubled charter school.
“And so for parents who wonder where my passions for kids with special needs comes from, I watched a year of kids not getting the special needs services they needed,” he said. “And it broke my heart.”
Connolly taught for three school years, from 1995 to 1998, between his own studies at Harvard and Boston College Law School. For the first two years, he was a volunteer teacher with the Nativity Mission School in New York, paid in room and board and a small stipend, though the job was full time and the hours exceptionally long, the Rev. Jack Podsiadlo, the school’s former president, said in an interview.
Connolly then taught one year and coached girls’ basketball at Renaissance, in the school’s third year after opening. Connolly says he was “drowning” at Renaissance, overmatched by a huge class size, the lack of school culture, and an atmosphere he calls chaos. He was not alone. Teacher turnover averaged 30 to 40 percent annually during the school’s first four years, according to the state Department of Elementary and Secondary Education.
“The year at the Renaissance really, really drove me to law school,” he said.
It was not the career he had expected as a Harvard senior, he said. Looking ahead to life after college, Connolly thought about joining the Jesuit Volunteer Corps or City Year, until he took the job at Nativity Mission. The school was in a converted red-brick tenement, with three floors of classrooms and one floor of housing for teachers who lived in apartments roughly the size of parking spaces.
Over two years, Connolly taught seventh and eighth graders, mostly Latin American immigrants — Dominican, Mexican, and Ecuadorian — or the sons of immigrants.
“Generally it was kids who just needed a second chance to try to escape what was happening in their neighborhoods,” said Jose Vilson, one of Connolly’s former students at Nativity, who is now 31. “These kids wanted to get a chance. They wanted to do right by their families. Some of us were academically proficient, and some of us weren’t.”
Connolly taught English, reading, history and one year of Latin, which he introduced into the school. Classes were generally small, 20 students or fewer. Connolly often worked from 7 a.m. to well after 9 p.m., teaching, coaching basketball, supervising afterschool programs, providing homework help at evening study hall, and even getting students back to the cavernous New York housing projects where many of them lived.
“Sometimes it would be his duty to drive the bus to take them home, because it was a very drug-infected neighborhood at that time,” said Podsiadlo.
“It was real poverty,” Connolly said. “And that was one of the things I remember: My kids loved being at school. They were not bothered by being there until 9:30 at night.”
Vilson, who said he appeared in a Connolly City Council campaign flier around 2005, now teaches eighth-grade math in Washington Heights
“One of my biggest lessons from him was how to use the verb ‘to be’ in my writing,” he said. “He was like, ‘Jose, you use the verb ‘to be’ too much.’ He just kept working and working with me, until I started working on my verbs and really trying to express myself a lot better.”
During the campaign, Connolly has said that he was not a great teacher.
Podsiadlo was much more generous.
“He was the kind of teacher we were looking for,” Podsiadlo said. “He understood that he was not in the school to teach a subject. He was in the school to teach middle-school, low-
income, immigrant boys. And that it’s not so much the amount of knowledge they acquired, but it was the way they became more humanized by their time in the classroom.”
Connolly had applied and was accepted at BC Law during his second year at Nativity, but was not excited about law school, he said.
“I really wanted to stay in education,” he said, thinking at the time that he would get on a track to become a principal. “I really wanted to seek out a public school in Boston and see if I was good enough to teach there.”
He sent out resumes and was offered a sixth-grade homeroom at Boston Renaissance Charter, a school that had opened in 1995 with 615 students.
The following year enrollment shot above 1,000, as it added its middle-school program, making it the largest charter school in the state at that time, according to a 1999 Department of Elementary and Secondary Education report.
In the initial years at the Renaissance School, it suffered poor state test scores and lots of discipline problems. The rapid expansion of the school led to “frequently disorderly, if not occasionally chaotic classrooms,” the report states.
“It was chaos; it was chaos,” Connolly agreed. “We had a lot of good teachers, but there was no school culture. And the school leadership was struggling. And all this [expletive] about charter schools taking the easiest kids — please! My kids are all coming out of Boston public schools, and the vast majority of them are behind grade level. I’ve got sixth-graders who are really smart, and they can’t put a period on the end of a sentence.”
Connolly’s class grew to 39 students of a wide variety of abilities, needs, and problems, he said.
“You spend all your time just trying to get your toughest kids through the day,” he said. “And the kids in the middle get ignored.” His eyes flooded. “And they are kids that could go any way. If you excite them to learn and show that you care about them, they’re going to take off. And if you don’t give them any attention, they’re just going to muddle and then ultimately wake up someday in a college, not ready for it.” He wiped away a streaming tear. “And this was, like, my first month at the Renaissance. I was drowning.”
Teacher Mitch Finnegan, a colleague of Connolly’s at Renaissance, said the school’s early years were “definitely the most difficult teaching situation that I’ve ever been in” over a three-decade career. “It was a struggle for all of us.”
Finnegan, now the director of wellness education for the Weston public schools, recalled that he was surprised when Connolly left teaching for law.
“It was sad for me to think as a lifelong educator that we were losing someone that good out of the field.”
James Vaznis contributed to this report. Mark Arsenault can be reached at mark.arsenault@