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Need a precedent for what’s going on in Boston politics? Look to 1993

Raymond L. Flynn’s resignation 28 years ago triggered a fierce contest to become the next mayor.

Boston mayoral candidates John Nucci, Tom Menino, Bruce Bolling, Rosaria Salerno, Bob Rufo, and James Brett joined hands during a mayoral forum at the Seaport World Trade Center on May 5, 1993.Wendy Maeda/Globe Staff

After intense speculation, a 53-year-old Irish-American mayor from a working-class neighborhood is tapped by a Democratic leader for a federal post, shaking up the city’s politics.

Boston has seen this movie before.

President-elect Joe Biden choosing Mayor Martin J. Walsh to be his labor secretary has a striking precedent. In 1993, Raymond L. Flynn was tapped by President Bill Clinton to become ambassador to the Vatican, setting up an open election to become the next mayor.

Mayoral transitions in Boston are relatively rare. And incumbents are notoriously difficult to beat: The last time it happened was in 1949. Even then, it only happened after James Michael Curley served time in federal prison earlier in his term.


So, 1993 sticks out in the city’s political history. Flynn’s departure triggered a series of events that led to the mayoral reign of Thomas M. Menino, who would become the longest-serving mayor in city history (1993-2014).

Flynn said Friday he took the ambassadorship because he thought “the Vatican could play an important role in [helping bring] peace and justice” in the world. And he suspects Walsh may have agreed to join the Biden administration for similar reasons.

“There are parallels, I think, with the reasons why Marty would want to serve in the Biden Cabinet, because he could make a contribution toward stability and bring people together,” he said.

Flynn’s departure also attracted a crowded field of candidates to replace him — something those with a front-row seat to the 1993 race expect to be repeated in coming months.

Joyce Ferriabough Bolling, a Boston political consultant whose late husband, Bruce, was the city’s first Black City Council president and a mayoral candidate in 1993, expects more people to enter this year’s contest. Anyone who enters the race now has “to have something that you can hold up to show that you’ve worked for the city in some way,” she said.


Sam Tyler, who was president of the city watchdog Boston Municipal Research Bureau in 1993, said he also expects “several quality candidates” will run for the mayor’s office.

“This opportunity doesn’t come up frequently,” Tyler said.

How large the mayoral field becomes when Walsh leaves for Washington, D.C., is an open question. Already, more than a half-dozen Boston politicos are said to be mulling it over, in addition to the two city councilors — Andrea Campbell and Michelle Wu — who already have announced their candidacies. Current council President Kim Janey, who would become acting mayor if Walsh is confirmed by the Senate, is among those thought to be considering entering the race. Political observers say that could give her an enormous advantage, as evidenced by what happened in 1993.

As council president at the time of Flynn’s leaving for the Holy See, Menino became acting mayor. That post gave him a wave of positive publicity as he represented the city, and helped catapult him to victory on Election Day

Menino was the top vote-getter in an eight-way preliminary contest in September 1993, then won a head-to-head with James T. Brett that November. At the time of the latter victory, he had been acting mayor for nearly four months. He cruised to reelection four years later, running unopposed.

Tom Menino went through paperwork after being sworn in as acting mayor as Ray Flynn departed for Rome on July 12, 1993.Pam Berry/Globe Staff/file

John Nucci, a former city councilor who ran for mayor in 1993, dropped out after Menino became acting mayor on July 12, realizing Menino immediately gained the upper hand. Nucci said last week that he needed to rely on Italian-American voters to a great degree to be successful at the polls in that race, and once Menino, a fellow Italian-American, was acting mayor, he knew he did not have a shot.


“Being acting mayor during the mayoral campaign is like being able to start the Marathon in Kenmore Square,” said Nucci. “It brings a huge advantage.”

Ferriabough Bolling thought Menino benefited immensely from serving as acting mayor in 1993.

“You can say, ‘I’m doing the job,’” she said. “That’s why you have an advantage.”

The city charter does place limitations on the acting mayor, stating the person “shall have no power to make permanent appointments.” Ferriabough Bolling, who thought much of Flynn’s power base went to Menino in 1993, said she wasn’t sure where Walsh’s army of supporters will go when he steps down.

The transition from Flynn to Menino was not without hiccups. Menino was infuriated by what he saw as Flynn’s lack of communication and cooperation during the transition, charges Flynn batted away at the time. On Friday, Flynn acknowledged that he and Menino had “different philosophies.”

Janey, in a statement last week, said she was looking forward to working with the Walsh administration and her council colleagues “to ensure a smooth transition” if the mayor is confirmed as labor secretary. At his State of the City address last week, Walsh said the transition to an acting Janey mayoralty has already begun and will continue smoothly.


In 1993, political adversaries took shots at Menino, saying that as acting mayor he should do little more than keep the city chugging along the path set by Flynn. The rationale from the critics was that since Menino was not elected by the people to city hall’s corner office, he was not entitled to make long-term decisions.

One rival mayoral candidate even filed a lawsuit in an attempt to impose severe restrictions on Menino’s powers. Some accused Menino of stealing their ideas as acting mayor. Whether Janey would face similar resistance if she were to run in the election remains to be seen.

To be sure, the political parallels between 1993 and today can be stretched only so far. Boston — and its politics — have changed in ways large and small. The city is more diverse now, for one. And neighborhood demographics and voter patterns have shifted, Nucci said.

Nucci said if Janey, who is Black, proves to be a dynamic leader as acting mayor, she could have an advantage in a mayoral contest in attracting voters who think the mayor of Boston — which is majority nonwhite — should be a person of color. Like Janey, the two city councilors who have publicly announced they will run for mayor, Campbell and Wu, are both women of color. By contrast, every Boston mayor so far has been a white man.


Timing is another difference. Walsh would leave with less than a year left in his term and months away from a regularly scheduled mayoral election. When Flynn left in 1993, his term was not slated to end for another two years. Nucci also remembered that the speculation regarding Flynn landing a Clinton administration post being much more prolonged than the recent round of Walsh-for-labor rumors.

Still, as in 1993, observers say Walsh’s exit is certain to attract a bigger field of candidates — including those who would never challenge an incumbent Boston mayor. In some ways, that is also like 2013, when Menino’s decision not to seek a sixth term sparked a dozen candidates to run. Walsh ultimately won that contest.

“It’ll be good for the city,” Flynn said. “It’ll bring people out.”

Jeremiah Manion of the Globe staff contributed to this report.

Danny McDonald can be reached at daniel.mcdonald@globe.com. Follow him on Twitter @Danny__McDonald.