City councilor to mayor? In Boston, it’s typically an uphill climb for challengers

Boston City Councilors Andrea Campbell (left) and Michelle Wu. The Boston Globe

More than a decade later, the stories are still fresh for Michael F. Flaherty: in his bid to unseat the city’s definitive powerhouse incumbent, then-mayor Thomas M. Menino, the city councilor pulled out the stops, buying advertising atop every taxi in the city and even paying for a plane promoting his candidacy to fly over Fenway Park on Opening Day while his campaign handed out leaflets to Red Sox fans below.

It was not enough. Despite Flaherty raising and spending $1.4 million during the 2009 race, Menino garnered 57 percent of the vote compared to the South Boston challenger’s 42 percent in the general election. It was the stiffest election challenge Menino faced during his two decades as mayor.

Which is to say: It’s tough for a city councilor to take out an incumbent mayor here, the potential road ahead for candidates Michelle Wu and Andrea Campbell if Martin J. Walsh decides to try for a third term.

In Boston, mayors wield great institutional power. By comparison, city councilors have much less solo sway. Mayors can cite constituent services like snow removal as a product of their leadership, and Walsh, if he runs, would be able to point to various policy accomplishments as his own.

In the words of Flaherty, “Nothing happens in Boston unless he signs it or if he gives his assent to it."

“The successes that the Boston City Council have had on a number of legislative efforts is solely attributed to his willingness to work with us," he said.

For sure, campaigns are more than simply a comparison of accomplishments. Personal stories and policy differences matter. Whether they matter enough to the city’s voters for them to kick out a sitting mayor for the first time in 70-plus years could be the central question of next year’s race.

Today, with the intriguing mayoral contest unfolding in the city, the first thing Flaherty mentions when rattling off the challenges a councilor faces when they run for City Hall’s fifth-floor corner office is money. Mayoral challengers, he said, should be looking to convey their message across every medium: television, radio, print, online, billboards, bumper stickers.

Flaherty estimated that in order to have a competitive campaign for mayor a million dollar war chest is a minimum necessity. That would mean that his two council colleagues who have announced mayoral bids have their work cut out for them on the fund-raising circuit.

Both Wu and Campbell entered this month with campaign coffers exceeding $400,000. Ten months before next year’s preliminary mayoral election, some things are very much in flux. Walsh has more than $5.7 million in campaign funding at his disposal, but he has yet to say whether he will seek a third term. While recent campaign activity, including raising more than $300,000 in the month of October, could signal a ramp-up to a reelection bid for Walsh, the mayor’s name has also been floated for potential posts in President-elect Joe Biden’s administration.

Wilnelia Rivera, a Boston-based political consultant who is not working for any mayoral campaign currently, said many campaigns that aim to unseat an established politician wrestle with a crucial question: Can the candidate generate enough support and raise enough money to become viable?

“Your job is to identify and go to your early adopters before you even launch your campaign,” said Rivera, who was the chief strategist for Ayanna Pressley’s successful 2018 congressional campaign against entrenched incumbent Michael Capuano. “If you haven’t done that and you think you can cut through the incumbency power early, it’s not going to happen. People will stay with Marty.”

For Rivera looking for the media to tell the story that a challenger can beat an incumbent is a fool’s errand.

“You can’t give it that much of your energy,” she said.

Mayoral hopefuls should use their life stories as leverage for having “the policy conversations we haven’t had as a city,” said Rivera.

Those stories are compelling ones for both councilors. Wu is the daughter of Taiwanese immigrants. She studied at Harvard and became first Asian American and first woman of color to serve as city council president. Campbell’s upbringing was touched by poverty and laced with tragedy. She would go on to study at Princeton and become the first Black woman to serve as council president.

If Walsh does run, making the campaign about a contest of accomplishments would be ill-advised for any challengers, according to Rivera.

“You’re going to be grasping at straws,” she said.

Former councilor John R. Connolly ran against, and lost to, Walsh in the 2013 mayoral contest. When Connolly first declared his intentions to seek the post, Menino, who died in 2014, was still in charge and had yet to say he would not be seeking another term. Weeks after his announcement, Menino said he wasn’t running, flipping the dynamics of the race on its head, according to Connolly, who said he went from a 30-to-40 point underdog to the frontrunner overnight.

“The whole thing changed on a dime,” he said.

Challengers are not going to raise as much money as the mayor, but that’s not the point, according to Connolly. Those looking to unseat a sitting mayor should focus on raising “just enough to run your campaign and get your message out,” a proposition that has become less expensive with the saturation of social media in everyday life, he said.

Connolly also spoke of the “changing political dynamics of the city,” noting the successes of Pressley and Suffolk District Attorney Rachael Rollins, who rose from a relative unknown to win the election for the county’s top prosecutor. Both are the first Black women to serve in their respective positions in the state’s history. Such successes may signal “a different kind of mayor’s race,” he said.

“Mayor Walsh will tout his eight years in office and Councilors Wu and Campbell will, I think, try to convey a vision for a change that may resonate with the changing Boston,” he said.

He described Walsh as a dogged campaigner, someone who works the phones hard and is adept at one-on-one politicking.

“He’s incredibly shrewd, politically,” said Connolly, and tipped his hat to the citywide campaign infrastructure Walsh built in 2013.

Flaherty, the city councilor who lost to Menino in 2009, also mentioned the importance of a strong ground game when mounting an insurgent mayoral candidacy. For him, the heart and soul of a serious citywide campaign meant 22 ward coordinators and 255 precinct captains, one for every precinct in the city. It also helps if a candidate has “an army of volunteers that will help you get your message out to the neighborhoods,” he said.

“They’re both going to have challenges taking on a popular, well-financed incumbent who is guiding the city through the pandemic and doing a good job,” said Flaherty of Wu and Campbell.

Councilors have made the jump from the city’s legislative body to the mayor’s office in decades past.

Menino’s predecessor, Raymond L. Flynn, won the mayoralty as a city councilor in 1983. But that was an open seat, as the longtime incumbent, Kevin White, decided not to run for another term. Flynn would be succeeded by then-city council president Menino after Flynn took the ambassadorship to the Vatican in 1993. Menino first became acting mayor in the summer of that year and went on to win a term outright in that fall’s election. He would serve in that role for the next 20 years.

Joyce Ferriabough Bolling, a Roxbury resident and Boston political consultant who hasn’t decided whom she is supporting in next year’s race, remembers Menino’s first mayoral win. Her husband, then-city councilor Bruce Bolling, came in fifth in the preliminary mayoral election in September 1993. To this day, she thinks that Menino serving as acting mayor in the immediate run-up to the race gave him a name recognition and publicity advantage.

“Absolutely, it mattered,” she said.

It’s an advantage any challenger to a seated Boston mayor will have to reckon with today, although Ferriabough Bolling is quick to point out the city has changed, and become more diverse, since 1993. Still, she is among those to label the jump from city council to mayor as difficult.

“It’s hard to match the mayor’s power, it really is,” she said, “but it’s not impossible.”

Jeremiah Manion of the Globe staff contributed to this report.