Some advice for Boston mayoral campaigns 

Lessons from the last open race for the city’s top job 

AN OPEN BOSTON mayoral campaign is often called a once-in-a-generation event. In fact, we had such a race only eight years ago, when Tom Menino retired after a record-setting 20 years in office. In 2013, a crowded field of 12 candidates vied in the September preliminary election, with the two top finishers, John Connolly and Marty Walsh, going on to compete in the November final election won by Walsh.   

I was the communications director for the campaign of one of those 12 — then-City Councilor Mike Ross. As this year’s race takes shape, I’ve been reflecting on what I learned through that experience, both the mistakes we made and the things we did well. So here is some unsolicited advice for current or prospective candidates looking to succeed Walsh as the city’s next mayor and those who work on their campaigns. 

Messaging Advice

  • Be able to explain your winning math. At the end of the day, a campaign is a math problem. How will you get to 50 percent of the vote + 1 (or the equivalent in a multi-party race)? In the upcoming race, you’ll need to explain two math problems: how do you win in a multi-candidate preliminary (by being one of the two top finishers) and how do you win in the head-to-head final election. Reporters, donors, and savvy political activists will not take you seriously if you can’t answer the question, “How will you win?” In 2013, I couldn’t really explain where our votes were going to come from (there was a plan, I was just bad at explaining it) and it hurt us. Every member of the campaign senior staff needs to be able to easily rattle off your winning path (e.g., door-knocking will bring out 40 percent of the vote in Mission Hill, mail will get us 5 percent in Southie). It can be aspirational, but it has to be specific and you have to know it cold. 
  • Don’t be afraid of attacking other candidates. In every election I’ve ever been in, we got the most attention when we criticized other candidates. In a multi-party field, conventional wisdom often says it’s bad to attack another candidate because, while you may drive voters away from that candidate, you don’t know for sure that those votes will go to you and you may end up driving voters turned off by the attacks to support other candidates. We thought this in 2013, and I’ve come to realize that we were being too clever. Don’t worry about votes moving in that way unless you are doing sustained negative mailers or negative TV (which you won’t have the money for). Attacking other candidates via a press conference is mostly a way to get you in the headlines. In a multi-candidate race, it’s also a way to try and define the campaign narrative as between you and someone else. Pick a target that would contrast well with you. There’s no real front-runner yet, or else I would say go after them. In 2013, a veteran campaign communications operative advised me that in a 12-person field we should be going after Marty Walsh because the contrast of Mike Ross and Marty Walsh worked in our favor. He was right, but I didn’t listen. The two press conferences we did have to call attention to aspects of then-state rep Walsh’s record were front-page news.
  • Single-issue candidate? One strategy in a broad field is to tie yourself to a single issue. It brands you in the minds of the voters as “The [insert issue here] candidate.” It’s frustrating to consider, as there are a ton of issues and candidates are a complicated and multifaceted human (like all of us). But it can really work. Make yourself the health care candidate, and relate every answer back to that issue — “Great question about education. Kids can’t learn if they are sick, so here’s my health care plan.” The challenge will come in the two-person final election, when you will need to pivot from your single issue to talk about things more broadly in order to capture the 50 percent + 1 needed to win. In 2013, John Connolly ran primarily on schools in the preliminary, and it seemed like he struggled to broaden his message in the general (which might be why he came up short). 
Meet the Author
Media Relations / Digital Communications Advice

  • Get over the lack of coverage. The big media, (the Globe, TV, et al) is not going to cover the race as much as you want — or as much as they should. When they do, it will be in big roundups. Probably each candidate will get a profile. There are not a lot of great ways to break out of this, so don’t beat yourself (or your press team) up. 
  • Focus on smaller outlets and online communities. Good media relations people will tell you to focus on local papers. There are weeklies and community papers across the city. Make sure they are part of your regular outreach. However, people are increasingly getting local news from online sources. Look for local blogs. Reach out to the admins of neighborhood Facebook groups to see if they will let you do virtual Q & As. Do an AMA (ask me anything) on God help you, think about how you can engage on Nextdoor.
  • Don’t be afraid of gimmicks. The Mike Ross campaign got a lot of great coverage by doing 24-hour campaign marathons, campaigning only via public transit for a week, and other things you could call gimmicks. If they are grounded in real issues, it’s nothing to be embarrassed about and can get you noticed. I was teased mercilessly for having a press conference featuring Mike standing next to a giant thermometer (on the hottest day of the year), but I’m proud we were talking about how poorer parts of the city are physically hotter than richer ones.
  • Make your own content. In 2020, Bernie Sanders had his staff making serious media products. They had podcasts, newsletters, and other substantial content. Much of it wasn’t even starring the candidate himself but rather his senior advisors. More campaigns need to do this. Great content will engage your supporters and introduce you to voters on an ongoing basis. In the digital age, content is how people know you! Start with a weekly newsletter about the week in the news and some campaign details sprinkled in. Create a video series explaining a different issue facing Boston. Or start a podcast interview series with a mover and shaker about the future of the city. There are a million ideas. Hire people who can make great content and let them do their thing. With the limits of engagement imposed by COVID, spending one day a week making your own media that is more interesting and in-depth than a generic press release will pay better dividends than a million calls to the Globe
Mayoral races in Boston are not really once-in-a-generation events anymore. But I’ve worked on all sorts of campaigns, and those for mayor are some of the most fun. The combination of local issues and a compact geographic area makes them feel more intimate and urgent. You’ll work alongside (and against) people who are as passionate about the future of your city as you are. You’ll visit parts of the city you never would have gone to in your regular life. You’ll subsist primarily on Dunkies and Simco’s while insisting that it’s fine, it’s fine. To all of you, good luck!

Josh Gee was communications director for Mike Ross’s 2013 campaign for mayor of Boston. He’s served as a digital and communications consultant for campaigns, nonprofits, and Fortune 500 companies and currently lives and works in New York City.