Robert Winters Is ‘Willing To Serve’ on Cambridge City Council. Will Voters Take Him Up On It?

Robert Winters has no campaign staff. He has raised less than $600, spent none of it, and refuses donations. He does not have a flashy campaign website, and his campaign does not have a social media presence.

But if elected to the Cambridge City Council, Winters insists, he is “serious about my willingness to serve” — and Cambridge voters can decide for themselves whether they’d like to see him in City Hall.

“The entire theme of my candidacy is, ‘Robert is willing to serve,’” Winter said in an interview last week, sitting in the Smith Campus Center. “And if you want that, that’s great. I’m available. If not, that’s fine too.”

Winters, a Cambridge resident since 1978, primarily works as a math instructor at the Harvard Extension School. But he has made a name for himself in the city as a blogger: Since 1997, Winters has run the Cambridge Civic Journal — an Internet-age equivalent to a paper of record, with regular updates on the City Council, local politics, and hot-button municipal issues.

He ran unsuccessfully for City Council in 1993, 1995, 1997, and 1999, though he never came close to Sullivan Chamber. (In an email, Winters wrote that, after 1993, he ran just “to help shape the debate.”) A comeback attempt in 2023 crashed amid scrutiny over controversial tweets by Winters — including one writing that “Islam and government don’t mix” — and heated opposition to him from the city’s Democratic Socialists of America branch.

Still, Winters shrugs off questions about whether his sixth campaign can succeed.

“To me, being an elected official is just another level of citizenship. You want to do that because you’re willing to make yourself available to do so,” he said. “Will my heart be broken? Will I weep uncontrollably if I’m not elected? Not at all.”

“That is fundamentally different than a lot of the candidates,” Winters added. “Their goal is to win at all costs, even if it means making shit up.”

Winters maintains a page on his blog dedicated to his candidacy instead of a formal campaign website, and he lists housing affordability as a top issue to tackle should he win a seat on the City Council.

Cambridge has “plenty of room for developing more housing, especially if you do it thoughtfully,” Winters said. But he added the caveat that surrounding municipalities should invest in housing as well.

“Cambridge doesn’t solve these problems unilaterally,” he said.

Winters is also a vocal opponent of Cambridge’s recent zoning overhaul, which saw the City Council end single-family zoning citywide and open up all of Cambridge to four-story buildings in a bid to lower housing costs by dramatically increasing Cambridge’s supply of homes.

He labeled the overlay a “Gargantuan Upzoning Amendment” in a February blog post, writing that the move poses fire safety risks and will fail to lower rents.

“Sometimes I think some of our city councillors are just robots created as part of an MIT project – programmed to solve some maximum-packing problem set with no sense of aesthetics, liveability, or community,” Winters wrote.

Winters has also used his blog to criticize the city’s attempts to expand bike lanes through a 25-mile separated network, which he labeled a “sacred cow” in 2024.

In an interview, he supported the City Council’s decision last October to push implementation of the bike lane network to 2027.

“I think there were good reasons for delaying it,” Winters said, adding that some existing bike lanes in the city resembled “hostile design” and have made driving in Cambridge much more difficult.

“Some of the designs of these bike lanes are ridiculous, really ridiculous,” he said.

Bike lanes and housing are just some of the many issues that Winters has spilled ink over for years. But his run for City Council — a job which Winters admits he would do even for free — is “just one more level of involvement” in local affairs.

“Maybe it’s possible to have more and more people who are more level-headed start to take interest in public service,” Winters said. “I like to believe that we can get better people to be serving in these positions.”

“I just think I would be one of them,” he added.

—Staff writer Matan H. Josephy can be reached at matan.josephy@thecrimson.com. Follow him on X @matanjosephy.