This fall, some Bostonians will pretend that holding office isn’t always the best way to win elections around here.

They must be stuck in 2013, the only time in decades that the big office in City Hall was really up for grabs.

Four years ago, longtime Dorchester state representative Marty Walsh weathered a 12-way race to win the open mayor’s seat. This time around, he’s an incumbent, with thousands of city employees to enlist as campaign operatives and way more money than all three of his challengers combined.

Walsh served for 17 years in the state legislature before becoming mayor. He’s the product of Boston’s old-school labor tradition, and his victory relied upon his ability to bridge the gap between that base and the city’s newer trend toward progressive politics.

Much like any incumbent, his first advantage is that he has concrete accomplishments he can point to when making his case to voters. According to the sheet of talking points his campaign gives to canvassers, the Walsh administration has overseen the construction of 19,000 homes, increased the BPS budget by hundreds of millions of dollars, and launched a $1 billion capital plan to renovate deteriorating school buildings.

Walsh also packs additional bona fides: He says he led police to favor an intervention approach, thereby reducing “unnecessary arrests” by 25 percent, while on the transportation front, his administration demonstrably created more bike lanes and improved crosswalks throughout Boston.

On the flip side of his record, however, is Walsh’s willingness to sell the city out to an attempted Boston 2024 Olympics bid, as well as the botched Seaport Indy Car Race that took similar liberties and could have also wound up on the backs of residents who got no substantial voice in the matter until shit hit the fan, spurring activists to intervene and bad actors to back out. On top of those blunders, it doesn’t look good that Walsh had to put his tourism chief, Ken Brissette, on administrative leave for allegedly extorting the organizers of Boston Calling to hire union labor, and get rid of his chief of health and human services, Felix Arroyo, for alleged sexual harassment.

Despite all that, and the deluge of concern about affordable housing coming from all angles, the incumbent has an advantage that a challenger can only dream about—the kind of leg up that, when removed from the equation like it was four years ago, drew more than dozen wannabe mayors into a dogfight. Holding the office that he’s running for, Walsh maintains a steady schedule of public appearances throughout Boston, for everything from special events to sporadic appearances at ceremonies celebrating city improvements. Plus the built-in legion of supporters that comes with the job.  

***

Walsh has roughly 18,000 city employees, many of whom are likely to see the benefits of maintaining the status quo.  

City employees are legally forbidden from using city resources, such as email accounts, to promote any political activity. But when a major component to serving as mayor is making public appearances, the line between official duties and campaigning can be blurred.

In January, right after Boston City Councilor Tito Jackson announced his intent to run against Walsh, the city’s attorney sent out an email to all employees with guidelines about campaign law. Employees were specifically instructed to refrain from using city resources for campaign purposes and were told that any volunteering must be done at night and on weekends—basically whenever they are not officially on city time and the taxpayer’s dime.

Despite such warnings, records obtained for this story show that in March, Walsh’s then-chief of staff Daniel Koh sent out a mass email to city employees urging them to march with the mayor in Boston’s annual LGBTQ Pride Parade.

Asked about a potential conflict of interest, a spokesperson for the mayor’s office explained that Koh’s email was on the level because he was only asking for city employees to march alongside Walsh toward the front of the parade, while his campaign was officially marching toward the rear of the parade.

In other words, Koh was only asking employees to march with the mayor. If they happen to hold campaign signs while walking alongside Walsh—which photos from that day show some of them did—that is their own prerogative, because Koh did not specifically ask for the signs.

Permitted to round up the troops through municipal channels, in a June email to city employees Koh asked for volunteers to accompany Walsh on his Mayor on Main trolley tour. This time, the email specifically asked that city employees who wish to join the mayor at his neighborhood stops do so after work hours or on the weekend—a distinction that ensures that the employees are following campaign law.

Herein lies the Walsh advantage, which often seems to occupy the gray between legitimate campaign activity and city events. If it looks like a duck and sounds like a duck, that’s fine. Just as long as nobody calls it a duck. Or admits that such behavior is potentially unethical.

At the time of this writing, according to the mayor’s office, no one has been formally disciplined for the emails we brought to the attention of administration spokespeople.

***

Jackson, who has served as the District 7 councilor for Roxbury since 2011, is Walsh’s chief rival. He chairs the council’s education committee, and he’s championing his work on the education front while also speaking out about the city’s lack of affordable housing.

“This is a mayor who signs off on the Boston Olympics and never read the full documentation,” Jackson told DigBoston for this article. “This is the same mayor who brags about the AAA bond rating that the city of Boston has, and was going to give it all away for a one-month party.”

The City Council often serves as little more than a bully pulpit, which means Jackson will not have the same luxury of pointing to his record that the mayor has. Any substantive ordinance from the council must be approved by the mayor, meaning he is able to take credit for most actions. At the same time, Jackson’s position to oversee budgets and the time that councilors spend in hearings learning the ins and outs of municipal government minutiae enable Jackson to make nuanced attacks.

“People are being pushed out of the city at a faster rate than I’ve ever seen in my lifetime,” he said. “About 87 percent of the housing is being built for the top 20 percent. Who is Mayor Walsh building for? Is he building for the people that live in Boston right now?”

***

John Hynes was the last person to defeat a sitting mayor. That was in 1949, and only after Hynes spent five months as acting mayor while the “Rascal King” James Michael Curley sat in prison on mail fraud charges.

Since then, voluntary resignation is the only thing that has been able to remove a Boston mayor from office. In part, that’s because regardless of whether or not City Hall employees volunteer in the campaign, Walsh can still expect to get a few votes out of each employee, including friends and family.

Cash flow always favors incumbency. The Walsh campaign keeps pulling in more money, maintaining a bank balance above $2 million for all of 2017, despite reporting spending an average of $159,000 each month. After getting used to the constant stream of polls in national politics, which are not as plentiful on the municipal level, campaign finances are an easy way to compare candidates with numbers. Jackson dismissed this metric.

“The mainstream reporting has only been on the piggy bank versus their actions or lack thereof. The reporting has been on fundraising, not people raising, not family raising,” said Jackson, who spun his comparative lack of funding as a positive.

“You won’t have to worry about those hooks being in my back because we are a grassroots campaign,” he said. “We are not beholden to the big dollars that this administration is beholden to.”

Nevertheless, it is hard to defeat an opponent who can outspend your campaign in a blink.

***

The last person who tried to beat a sitting mayor was then- and current City Councilor Michael Flaherty when, in 2009, he masochistically ran against Thomas Menino.

Flaherty said that a mayor running for re-election has a major advantage in terms of available resources. From money that’s been raised over the course of a four-year term to having plenty of city employees who are able to take administrative leaves in order to work for the campaign and the ability to turn every city improvement, large or small, into a promotion.

“Citywide campaigns are difficult, and they are increasingly expensive,” said Flaherty. “You’re running to be the CEO of Boston. With that comes significant effort and significant responsibility. You’ve got to scratch and claw and meet as many voters as you can. You need to be meeting people in volume.”

By the end of the 2009 election, Menino won with 57 percent of the vote. It was the closest race he ran in his 20 years in office.

“Tito has a heavy task in front of him,” said Flaherty. “It’s not completely insurmountable, but several factors will have to break his way in order for him to remain competitive.”

Larry DiCara, a former city councilor, mayoral candidate, and longtime Boston politics historian, was more dismissive of Jackson’s chances.

“This is a nonevent,” he said. The closest that DiCara’s seen a candidate come to unseating an incumbent mayor was in 1975 when Joe Timilty challenged Mayor Kevin White, an anomaly that he says had much more to do with the state of the city than the quality of either campaign.

“The city was on its knees financially, and we were in the middle of a desegregation order,” DiCara said. At the end, White held on with 52 percent of the vote, and he then defeated Timilty again in 1979 with 54 percent.

“I expect that Marty will win and win handily,” added DiCara, who himself made a go for the corner office in an open race in 1983. “I expect he’ll do well in most every neighborhood in the city … Tito will try to make some points, but I think it’s a very tough argument because times are about as good as I’ve seen.”

***

This year’s race for mayor also includes two candidates who are less established than Jackson and Walsh. Both are running their own DIY campaigns, so there was no organization or office to visit.

Lifelong East Boston resident Bob Cappucci, 72, served as a police officer for 15 years, a Boston Public Schools substitute teacher for six years, and as a member of the Boston School Committee for four years during the 1980s, when the committee was still an elected position. He also worked as a vice president for the East Boston Community Development Corporation, which promotes and creates affordable housing in the neighborhood, so despite being a dark horse, the candidate is well-equipped to debate housing and schools.  

Much like every other challenger, Cappucci is quick to criticize the city’s lack of affordable residences. Unlike his fellow candidates, he has vowed to place a moratorium on all real estate development.  

“I think there’s much more interest in building as opposed to the people,” said Cappucci.

“You get out there and you listen to people. Someone has to help them, and I don’t think they’re being helped.”

Cappucci is also leaning on his education experience as a former member of the school committee. He plans to make the city’s exam schools more accessible, and he would like to reorganize all of the public schools into four tiers, ostensibly different than today’s four-tier system.

Unlike Walsh and Jackson, Cappucci is running an extremely small operation. In three months of fundraising, he brought in $15,500, with $13,000 of it coming from himself. That money has primarily gone toward 200,000 advertisement cards, with the rest of his campaign work focused on door knocking and pressing the flesh.

“Incumbency always has the advantage,” he said. “Any candidate, if you make the decision to run, you just have to work harder than the incumbent. I’m campaigning 20 hours a day. I only get four hours of sleep. It’s an awful lot of work.”

Aside from cash, Cappucci may also struggle among the city’s many progressive voters. Among his campaign pledges is to do away with Boston’s status as a sanctuary city.

“There are an awful lot of people that disagree with the sanctuary city. I personally don’t feel that the voice of the citizens of Boston has been heard. They do not want a sanctuary city.”

Cappucci is also the only anti-abortion candidate in the race. He told the host of a BNN anti-abortion show that he suspected that politicians who adopt a pro-choice stance often do so to access campaign financing from national pro-choice organizations.

“Am I the perfect candidate?” he asked. “Nobody is, but I would love to be a decent mayor.”

***

Joseph Wiley, who also hails from East Boston, is running perhaps the most quixotic campaign.

Sixty-eight years old, Wiley is originally from Roxbury and spent time living in San Francisco and New York City before returning to Boston about two decades ago. He says that he came of age in the 1960s, which fuels his idealism about public service, and that it was President Barack Obama’s call to action in his farewell address that inspired Wiley to try politics.

“I’ve seen how effective an activist government can be if you actually have an activist leader,” Wiley said. “The purpose of holding political office is to actually do something about the problems a majority of your constituents face.”

The sorry states of affordable housing and the city’s school system inspired him to go for the top office in Boston. Wiley argues that even though the city requires 13 percent of the units in every development to be designated as “affordable,” those homes still often remain out of reach for most residents.

“Half of the city makes $35,000 or less,” said Wiley. “It’s certainly not affordable to them.”

Wiley also said that he would like to improve the homelessness situation in Boston.

“There are 3,000 Boston school students who are homeless,” he said, citing a figure that was widely reported last spring.  

Wiley is candid about his lack of campaign funds. So far, he’s only spent about $9,000 on a professional signature gatherer just to get on the ballot, and a few hundred more on a website, leaving about $300 in the bank.

“I don’t have any money, so you aren’t going to see any flyers,” he said. Instead, he said he hopes to get as much free press and publicity as possible.

In Boston, even before anyone decides to go head-to-head with monolith incumbency, the credibility of every candidate is determined and driven by media assumptions. In this case, it was decided almost a year ago that the race for City Hall was between Marty and Tito, two men on a first-name basis with Boston.

So stuck are these foregone conclusions that, according to Wiley, some reporters have assumed he has an ulterior motive for running and have asked if he is a clandestine ringer who was encouraged to join the fray to undercut Jackson. But while the theory of Wiley as a candidate-operative may look interesting or even politically sexy on paper, it doesn’t makes much sense. For starters, before the general election in November, there is a preliminary on Tuesday, Sept 26, after which the field of candidates will narrow down to two. So unless Wiley finishes second, this is still by all means a race between Jackson and Walsh. Even if you buy the story that the purpose is to force Jackson to spend more campaign dollars, why would the Walsh machine leave Wiley so pitifully understaffed?

Wiley, and Cappucci for that matter, seem to be involved in this race because they believe that they have something to add to the political conversation and because they both want to talk about housing and schools without worrying about burning any potential donors.  

That’s probably why, in this election and innumerable others, the incumbent refuses to take part in debates before the preliminary. Who wants to be challenged by someone without much to lose?