Who’s Afraid of Marty Walsh?

Walsh also makes sure to remain in the public eye, keeping a dogged pace of appearances—community meetings, lunches with the elderly, ribbon-cuttings—comparable to the indefatigable Menino’s. He tells me that by the end of this school year he will have visited every one of the city’s 128 public schools. He holds “Mondays with the Mayor” every other month to take public questions, and appears regularly on local radio programs. His staffers maintain a real-time map of Walsh’s sojourns to the neighborhoods to ensure that he’s hitting them all. According to Walsh’s chief of staff, Dan Koh, the mayor sends a personal note to everybody who hands him a business card. “I’m a workaholic,” Walsh says. “Boston is a working-class city, where people expect to see the mayor at a Little League game or at a senior luncheon.”

In addition, Walsh has made inroads with large special interests that might choose to back an opponent. That includes the city’s business leaders, who viewed Walsh warily in 2013 as the pro-union candidate. “Among businesspeople three or four years ago, some thought that if he’s mayor, he’ll give away the store,” says Lawrence DiCara, a former city councilor and a Boston political historian. “He hasn’t given away the store.” Instead, Connolly says, “The most effective part of his four years is how he’s advanced his housing and development agenda, which the union cares about and the business community cares about.”

On the always-combustible issue of additional charter schools, Walsh—usually a proponent—came out against the recent ballot Question 2, which sought to raise the cap on charters. Walsh may have believed in the idea, but he decided to play smart politics: By condemning the measure, he assuaged wary teachers union members who helped him in 2013 because of their greater antipathy toward the reform-minded Connolly. “Marty’s played it right,” says an elected official in Boston who wished to remain anonymous to avoid appearing to take sides in next year’s election. “He’s pro-charter but against Question 2. There’s not enough daylight” for someone to run against him on the issue.

Reelection Is Built Into the System

It’s an understatement to say that Walsh has history on his side. The last time an incumbent mayor lost a bid for reelection in Boston was 1949; James Michael Curley, approaching his 75th birthday, was coming off five months in prison for mail fraud and still only lost by 11,000 votes.

That was also the year Massachusetts changed Boston’s charter, establishing the preliminary election that narrows the field to two final choices. That made reelection more difficult—Curley had previously been able to squeeze through with pluralities against crowded fields—but also reaffirmed the strong-mayor government that many point to as a mayor’s ticket to reelection. In Boston, DiCara says, “The mayor controls the purse strings.”

Politically, Walsh understands that power. DiCara, for instance, points to the many different organizations that currently have contracts with Boston Public Schools. That translates into a lot of grateful employees and parents. Similar ripple effects can be found in healthcare, public safety, development, and many other fields. “It is virtually impossible to beat an incumbent mayor,” Connolly tells me. “Short of complete incompetence, they’re going to have key political factions in their favor.”

It’s also harder than ever for Boston politicians to build the type of citywide reputation needed to defeat a sitting mayor. When DiCara ran for the job in 1983, the city council was still a prominent platform for ambitious pols: Up until that point, members were elected citywide, a system being replaced that year, and a large City Hall press corps kept them in the news. Today, only four of the 13 councilors appear on ballots outside their neighborhoods, and the depleted local news industry barely takes notice of them.

There are other systemic reasons why so few have the status, the name recognition, and the nerve to emerge as a serious challenger to Walsh. In days gone by, the Boston School Committee served as a political steppingstone, but the 1992 change from elected to appointed positions has turned it into a cave of anonymity. For 20 years, Menino discouraged his top talent from gaining too much public credit—a self-defense strategy to protect himself that still contributes to the lack of local political stars willing to take aim at Walsh. Plus, in this Democratic Party–dominated state, a long-standing wait-your-turn ethos discourages any challenges from within. “The Massachusetts Democratic culture is ‘don’t rock the boat,’” Connolly says. Despite the occasional exception, such as Seth Moulton challenging and beating incumbent Congressman John Tierney in 2014, the prevailing attitude is that everyone should support the incumbent.

No Critics, No Worries

With few critics making daily headlines, there’s not much chipping away at Walsh’s image. This helps him maintain high polling numbers, which in turn makes it that much harder for others to take on the challenge of running against him. It’s no surprise, in other words, that the most effective thorn in Walsh’s side over the past three years was not some well-known politician but a cadre of no-name grassroots organizers under the banner of “No Boston Olympics.”

The lack of political detractors is further exacerbated, some say, by the age-old assumption, prominent during Menino’s days, that anyone criticizing the mayor of Boston will be stamped out. “I have a different approach,” Walsh tells me. “I don’t feel that the vindictive way is the way to govern.” Still, whether it’s true of Walsh’s administration or not, the perception might account for why certain potential critics are holding their tongues.

That might also help explain why Boston pols don’t see the value in a common political tactic: running against the incumbent to boost one’s political status and visibility, hoping to win now but with an eye toward running even stronger four years later. While insiders say that might be the thinking luring Tito Jackson into the race, “There’s no history of that” gambit working as a path to mayor in Boston, says DiCara—who never tried again after his own losing bid. John Powers, Louise Day Hicks, and Joe Timilty all lost and later tried a second time, without success. In Boston, there is a sense that one swing at the king is all you get.

Walsh Might Not Stay Long, Anyway

Walsh knows what it’s like to want to be mayor of Boston, uncertain of when the chance might come. In the city’s recent memory, mayors have tended to stay put for a long while: Prior to Walsh, there were only three in 45 years. “We were all kind of waiting,” Walsh says of himself and the other 11 candidates who ran in 2013 after Menino decided not to seek reelection. “If the mayor ran another term, my window might have closed.”

Now, Walsh knows he’s the one being watched. “There’s a lot of newer politicians out there,” he says. “They’re deciding, is this their time, or do they wait?” Insiders suspect that Walsh, though still shy of 50, might not have designs on a long-term lease at City Hall. Instead, he might follow in the footsteps of former Governor Deval Patrick, known for staying only two full terms despite the lack of term limits. “People assumed Tom Menino was going to be a 20-year mayor,” says City Councilor Matt O’Malley. “People may not expect Marty to serve 20 years the way Mayor Menino did.”

That could be a major reason why challengers aren’t lining up against Walsh. Why take on an incumbent when you can wait a few years and take a shot at an empty seat?

Walsh himself says they’re probably right—that he doesn’t see himself hunkering down for “many terms” as mayor. Still, the future is hardly set in stone. If Walsh settles in comfortably on the fifth floor, and other suitable opportunities fail to appear—Hillary Clinton’s loss, for example, likely erases the chance of a cabinet position any time soon—Boston’s ambitious pols might someday look back at 2017 with regret, wishing they’d tried to oust Walsh while they still had the chance.