It is the missing link in John R. Connolly’s biography. The one you will not hear about on the campaign trail. For all his talk of his experience as a teacher, Connolly has spent far longer, 12 years, as a lawyer.
His legal career has taken him into the offices of Ropes & Gray, one of the city’s top law firms, where as an entry-level lawyer he assisted in corporate transactions, including the leveraged buyout of a large private company. He has worked in bankruptcy law, and became a partner at his own small firm, where he handled minor business transactions while spending the bulk of his time on the City Council.
But Connolly rarely mentions his work as a lawyer, insisting the law “was never where [his] heart was.” He emphasizes that he doesn’t “have anything to hide,” but has steadfastly refused requests to release his client list for that legal work, citing attorney-client privilege.
He says he has appeared before a judge only once in more than a decade as an attorney, and cannot even recall the nature of the case.
As Connolly tells it, the law was just a way to pay the bills. From nearly the outset of his legal career, he was preoccupied with another idea.
“I was always feeling the pull to do something in education or service,” Connolly said. It was the same call that drew his father, a former secretary of state, and his mother, the former chief justice of the state district court system.
Like his mother before him, Connolly attended Boston College Law School, after his three years of teaching. While there, he secured a competitive summer associate position at Ropes & Gray, one of the biggest firms in the city, paving the way for him to join the firm’s corporate department after his graduation in 2001, at age 27.
The hours were excruciating, but the money generous for a new attorney, more than $100,000, Connolly said.
“He was learning his trade as a business lawyer,” said Mark V. Nuccio, a partner at the firm, who mentored Connolly. “The stuff he did was pretty vanilla stuff that any young business lawyer would do.”
Michael T. Marcucci, a friend of Connolly’s who graduated from Boston College with him and sent a letter endorsing his application to the Massachusetts bar, later joined him at Ropes & Gray.
“When you’re a junior associate at a place like that, you do the work that you’re assigned,” said Marcucci. “I think it’s a regular, normal career path for a young lawyer.”
Neither Connolly nor Ropes & Gray would release a list of his clients, but an online biography describes some of the work he did during his 2½ years there. It said he was involved in “representing an investor syndicate in a leveraged buyout of a large, privately held publishing company.”
Connolly said he was one of the junior lawyers on the project, tasked with due diligence: going through “boxes and boxes and boxes” of the company’s paperwork and summarizing it for senior lawyers at the firm.
He said he was more directly involved with the firm’s representation of the original owners of an air freight company, taking the lead on negotiations when they bought back the business from a publicly traded parent organization.
He also engaged in pro bono work, helping a private school, for example, obtain nonprofit status.
The grueling 80-hour weeks wore on the recently married lawyer, just 30 years old at time. “I was never seeing my wife because I was always at the firm,” he recalls.
In April, 2004, Connolly left Ropes and began working for the midsized law firm then known as Hanify & King,telling lawyers there he was interested in doing more litigation work.
“This young guy shows up with these natural gifts and talents and says I want to do more advocacy on my feet,” said John Hanify. “I want to learn the skills of a trial lawyer, so throw me into it.”
As at Ropes & Gray, Connolly said, his salary at Hanify & King “hover[ed] around a little over” $100,000.
To help him earn litigation experience, Hanify said, the firm assigned Connolly to bankruptcy work. He recalled the new hire assisting on several cases, including one that involved researching Slovakian business law.
But by then, Connolly was already seriously considering a move to politics. Ultimately, by his own admission, he “didn’t really do litigation.” In his entire careeer, he said, he argued just one motion in front of a judge.
By 2005, the year after he joined Hanify & King, he took a leave of absence to make what would be an unsuccessful run for City Council.
“I insisted it be only a leave,” Hanify said, “because I wanted him to come back.”
But he would not be back for long. By April 2007, Connolly parted ways with the firm and made his second bid for the City Council, that one successful.
The next month, he joined two other lawyers as the third partner at what became Schofield, Campbell & Connolly, joining a general practitioner, Tim Schofield, and Cathleen Campbell, who practiced mostly criminal law.
“He left because he wanted to do more work for public service, so I think he created more of an option, which was to have a small professional organization where he could practice law part time,” Hanify said. “We wanted lawyers full time.”
In many ways, that City Council election marked a delineation in his legal career. No longer was he working long hours and collecting a large legal salary. His $87,500-a-year city duties became his priority. Legal work took on a secondary role. In some years, it appears to have played almost no role at all, according to public filings.
Connolly said he has represented only about 30 clients since he became a city councilor in January 2008, doing mostlybusiness transactions. His contention on the campaign trailthat his legal practice has played a small part in his professional life in recent years is backed up by the financial disclosure forms he is required to file as a city councilor.
Those disclosures show that in 2008, his highest-earning year since he took office, Connolly’s legal income was between $40,001 and $60,000, though he said the money was derived from the way his partnership in the law firm was structured and ultimately he had to pay “a good chunk of that back.”
In 2009, he reported earning $5,000 or less from his private practice. In 2010 and 2011, he made $20,000 or less, the disclosures show, while last year, he took in $5,000 or less. Connolly says he did only about 10 hours of legal work in 2012.
Tim Schofield, Connolly’s former partner and the cochair of his campaign, would not comment on the nature of Connolly’s cases at their firm, but said that each of the firm’s partners performed separate work and had their own unrelated clients. Connolly, he said, had the fewest.
“We were sort of a bread-and-butter law firm, we all had our own practices, we did our own thing, and we basically shared space and expenses,” Schofield said, adding that Connolly, “didn’t practice a whole lot of law in the time he was with us. Between the campaign and being a city councilor, he really spent a vast majority of time out of the office.”
By October 2012, four months before Connolly announced his mayoral campaign, the firm split up. Connolly’s bar license now lists his home address.
Although Connolly has given a few examples of the work he did at that firm — helping a Web start-up develop a confidentiality policy, advising a community theater on how to structure its business — he has refused to identify any of his clients over the five years he was a partner, citing attorney-client privilege.
In a variety of interviews over the last week, Connolly denied the Globe’s requests to release a full roster of his clients, despite repeated questions.
Legal analysts agree that the ethical code prohibits Connolly from identifying those who he has represented. But there are exceptions. If a lawyer represents someone in open court, or signs his name to a public legal document, for example, his connection to his client would already be in the public domain.
Connolly could also ask his clients to release him from confidentiality. For example, Schofield, who ran unsuccessfully for a state Senate seat two years ago, lists on his firm’s website 58 clients the firm has represented.
Connolly has refused any such disclosure.
“I’m under an ethical canon that says client confidentiality is above all else,” he said.
His mayoral opponent, Martin J. Walsh, has made Connolly’s lack of transparency about his career a campaign issue and has called upon Connolly to “open up his law practice.”
Connolly has also faced questions about his firm’s involvement in eviction proceedings. In one case, Connolly’s legal associate represented a housing management company that was moving to evict tenants, including a woman who said she could not pay her rent because she was on dialysis.
Connolly has acknowledged the law firm represented landlords, but has said that he was never involved in such cases.
A labor group supporting Walsh knocked Connolly in a recent flier for being “a corporate lawyer,” adding that one of Connolly’s former firms trumpeted its work defending employers against discrimination claims.
Connolly strenuously denies ever doing that kind of work.
“I was a business transactional lawyer; I never did anything remotely involving that type of law,” he said. “That’s not what my practice was.”Joshua Miller can be reached at email@example.com. Follow him on Twitter @jm_bos. Milton J. Valencia can be reached firstname.lastname@example.org. Follow him on Twitter @miltonvalencia.