headshot of candidate

Robert Winters

He/Him

Election history
6th time running (ran in the 90s)

More about Robert Winters

Robert Winters is perhaps best known in Cambridge for maintaining a blog, titled Cambridge Civic Journal, about Cambridge politics; his notes about City Council meetings going back to 2006 are still available at his website. He started including videos, often with guests, in 2014. And he puts together a page with straightforward, non-editorialized candidate information for every election.

A mathematics PhD, Winters has taught at several area schools, including BU, MIT, and Harvard. Beginning in the 1980s, Winters served in several civic capacities, including in early initiatives with Cambridge's nascent recycling and composting programs, and on several boards and committees.

He has also been active on Twitter for many years. He has a long history of posting, engaging with, and liking content there that other people and organizations classify as transphobic, racist, sexist, Islamophobic, and pro-retaliatory-violence. For instance, he followed the well-known far-right, anti-LGBT+ LibsofTikTok account, and drew their attention to a local drag queen event at the Cambridge Public Library. Since that account is notorious for inciting violence, the Cambridge Police ended up deploying to protect residents in response.

When questioned about this history at a candidate forum in 2023, he said he didn't remember or liked something he found funny.

A perennial challenger candidate, Winters first sought election in the 1990s.

Incumbent
No
Education
  • BS, Queens College
  • MIT
  • PhD, Boston University
Age
70 years, 5 months
Born in 1955
Voting
Reg. Feb. 2, 1980
History Updated soon, we hope!
  • 🗳️ 2024 Presidental Primary - Democratic
  • 🗳️ 2024 General Primary - Democratic
  • 🗳️ 2024 General
  • 🗳️ 2023 Municipal
  • 🗳️ 2022 General
  • 🗳️ 2022 General Primary - Democratic
  • 🗳️ 2021 Municipal
  • 🗳️ 2020 Presidental Primary - Democratic
  • 🗳️ 2020 General
  • 🗳️ 2020 General Primary - Democratic
  • 🗳️ 2019 Municipal
  • 🗳️ 2018 General Primary - Democratic
  • 🗳️ 2018 General
  • 🗳️ 2017 Municipal
  • 🗳️ 2016 Presidental Primary - Democratic
  • 🗳️ 2016 General
  • 🗳️ 2016 General Primary - Democratic
  • 🗳️ 2015 Municipal
  • 🗳️ 2014 General Primary - Democratic
  • 🗳️ 2014 General
  • 🗳️ 2013 Special Primary - Democratic
  • 🗳️ 2013 Special
  • 🗳️ 2013 Municipal
  • 🗳️ 2012 General
  • 🗳️ 2012 Presidental Primary - Democratic
  • 🗳️ 2012 General Primary - Democratic

Where Robert Lives

Address
Owns at 366 Broadway
Valued at approx. $1,675,000
Last sold Sept. 11, 1995 for $185,000
inflation adjusted approx. $391,000

Robert on Housing

Proposal Supported?
MFZ
AHO #3
AHO #2
AHO #1
Upzoning Central Square n/a

In general, Robert Winters does not support subsidized housing, nor many market-rate housing initiatives, nor increasing tenant protections.

He has spoken in favor of building taller along Mass Ave, but at lower heights than what CDD has recommended.

No. I didn’t support he original “Affordable Housing Overlay” as written or as originally proposed when I was a member of the Envision Cambridge Housing Working Group, and the current proposal is worse. There are far better and fairer ways to do this. It should not just be about maximizing the number of subsidized units.

Robert Winters , ABC Survey, 2023

Cambridge is already is one of the most densely populated cities in the state and the country. There are some opportunities for additional growth, but I would not support wholesale disruption to the residential character of Cambridge.

Robert on Other Issues

Proposal Supported?
CSO
Broadway
Garden Street

Then there’s The Bike People, their irrational beliefs, and their total disregard for any residents who travel on more than two wheels.

I just wish there was a clear “reasonable” political tent under which some of us could comfortably camp out.

Endorsements for Robert

Q&A

Interviews with Robert

Press

Articles about or by Robert

Cambridge Day Cambridge’s big influence groups draw scrutiny from City Council candidates at a pair of forums

Winters, who was not born in Cambridge but had even native son McGovern deferring to his encyclopedic knowledge of Cambridge political history, said the council could sometimes decide to pursue “the shiny new thing, and sometimes the shiny new thing is going to get tarnished pretty quickly.” He said it was important to bring in new perspectives.

Sept. 23, 2025 — Michael Fitzgerald
Cambridge Day Cambridge’s big influence groups draw scrutiny from City Council candidates at a pair of forums

Winters, who was not born in Cambridge but had even native son McGovern deferring to his encyclopedic knowledge of Cambridge political history, said the council could sometimes decide to pursue “the shiny new thing, and sometimes the shiny new thing is going to get tarnished pretty quickly.” He said it was important to bring in new perspectives.

Sept. 23, 2025 — Michael Fitzgerald
The Harvard Crimson Longtime Civic Blogger Robert Winters Is Running for Cambridge Council. Now, He’s Facing Political Scrutiny of His Own.

But the longtime Cantabrigian denied allegations that he is racist, transphobic, or Islamophobic, which he wrote in an Oct. 2 blog post are part of a “full-fledged campaign of harassment and intimidation.”

Still, Winters stood by his social media posts, including a post alerting the popular far-right TikTok account Libs of TikTok to a drag story hour at the Cambridge Public Library — which prompted the Cambridge Police to send an officer to the event — and a post where he wrote that “Islam and government don’t mix.”

“I’m sorry if anyone failed to appreciate my sense of humor (actually, I’m not really sorry) or failed to see either the irony or the absurdity of something I said over the last quarter-century,” he wrote in the Oct. 2 blog post, accusing his critics of using “the tactics of Joseph McCarthy.”

---

To Winters, a problem with BEUDO is the “obsession” with “requiring retrofits of buildings via mandate without any regard to practicality and expense.”

Winters said he does not support city funding for HEART, a local police response alternative, and that the criticism towards the Cambridge Police Department “is not fair.”

“I think we actually have a pretty good police force in Cambridge, when you compare it to almost anyplace else in Massachusetts, if not the whole country,” he said. “Does that preclude the possibility that maybe somebody could make an error? Of course not.”

Oct. 10, 2023 — Jina H. Choe
The Harvard Crimson Longtime Civic Blogger Robert Winters Is Running for Cambridge Council. Now, He’s Facing Political Scrutiny of His Own.

But the longtime Cantabrigian denied allegations that he is racist, transphobic, or Islamophobic, which he wrote in an Oct. 2 blog post are part of a “full-fledged campaign of harassment and intimidation.”

Still, Winters stood by his social media posts, including a post alerting the popular far-right TikTok account Libs of TikTok to a drag story hour at the Cambridge Public Library — which prompted the Cambridge Police to send an officer to the event — and a post where he wrote that “Islam and government don’t mix.”

“I’m sorry if anyone failed to appreciate my sense of humor (actually, I’m not really sorry) or failed to see either the irony or the absurdity of something I said over the last quarter-century,” he wrote in the Oct. 2 blog post, accusing his critics of using “the tactics of Joseph McCarthy.”

---

To Winters, a problem with BEUDO is the “obsession” with “requiring retrofits of buildings via mandate without any regard to practicality and expense.”

Winters said he does not support city funding for HEART, a local police response alternative, and that the criticism towards the Cambridge Police Department “is not fair.”

“I think we actually have a pretty good police force in Cambridge, when you compare it to almost anyplace else in Massachusetts, if not the whole country,” he said. “Does that preclude the possibility that maybe somebody could make an error? Of course not.”

Oct. 10, 2023 — Jina H. Choe
Loren Crowe's Medium How a City Council Candidate’s Online Bigotry Exposed Cambridge Children to Far Right Danger

In June 2022, Libs of TikTok was putting together one such harassment campaign by publicly building an online list of Pride events around the country that were being marketed as age-appropriate for children and families. Such events are common, a regular part of most cities’ Pride Month programming. After all, LBGTQ+ kids exist, most of your queer friends will confirm that they knew who they were before they turned 18, and children deserve to feel proud of and loved for who they are just as much as any adult.

Libs of TikTok disagrees, and put out a call for its followers to add events in their own communities to a running public list. Robert Winters quickly complied and provided the Libs of TikTok list with a date, time, location, and link for a Drag Queen Story Hour event for LGBTQ+ children and families being hosted by the Cambridge Public Library during the first week of Pride Month.

Oct. 4, 2023 — Loren Crowe
Loren Crowe's Medium How a City Council Candidate’s Online Bigotry Exposed Cambridge Children to Far Right Danger

In June 2022, Libs of TikTok was putting together one such harassment campaign by publicly building an online list of Pride events around the country that were being marketed as age-appropriate for children and families. Such events are common, a regular part of most cities’ Pride Month programming. After all, LBGTQ+ kids exist, most of your queer friends will confirm that they knew who they were before they turned 18, and children deserve to feel proud of and loved for who they are just as much as any adult.

Libs of TikTok disagrees, and put out a call for its followers to add events in their own communities to a running public list. Robert Winters quickly complied and provided the Libs of TikTok list with a date, time, location, and link for a Drag Queen Story Hour event for LGBTQ+ children and families being hosted by the Cambridge Public Library during the first week of Pride Month.

Oct. 4, 2023 — Loren Crowe
The Harvard Crimson Cambridge Activists Protest Council Candidates After Racist, Transphobic Social Media Activity Comes To Light

In one such tweet, Winters is quoted as writing, “Keep the chains on the protestors. They’ll go well with the leg irons #StupidLivesMatter.” The flier also includes Pasquarello’s liked tweets, one of which includes the statement, “We’ve been told that teachers talking to kids about sex (fantasies, orientation) doesn’t lead to grooming!”

...

In a Thursday interview, Winters called the accusations against him “completely uncalled for and unfair,” adding that they were “clearly motivated by hostility.”

“Sometimes I think things are funny, no matter where they come from,” he said. “I don’t think anybody should be censoring my right to laugh at what I think is funny.”

Oct. 2, 2023 — Muskaan Arshad, Julian J. Giordano
The Harvard Crimson Cambridge Activists Protest Council Candidates After Racist, Transphobic Social Media Activity Comes To Light

In one such tweet, Winters is quoted as writing, “Keep the chains on the protestors. They’ll go well with the leg irons #StupidLivesMatter.” The flier also includes Pasquarello’s liked tweets, one of which includes the statement, “We’ve been told that teachers talking to kids about sex (fantasies, orientation) doesn’t lead to grooming!”

...

In a Thursday interview, Winters called the accusations against him “completely uncalled for and unfair,” adding that they were “clearly motivated by hostility.”

“Sometimes I think things are funny, no matter where they come from,” he said. “I don’t think anybody should be censoring my right to laugh at what I think is funny.”

Oct. 2, 2023 — Muskaan Arshad, Julian J. Giordano
Robert Winters' Blog Now It’s My Turn To Speak

I was surprised to learn that in some public libraries there were “drag time story hour” events taking place that were publicly funded. On that same day I saw that one was taking place in Cambridge and simply made a note of this fact – and for this I was called a transphobe.

Fact: I really had never heard of such a thing – even though people apparently argue about this all the time now. In case you actually care what I think, I don’t believe it is age appropriate to subject young children to things that are either sexually provocative or overtly political. I understand that some people in Cambridge have a different point of view on such matters, but I daresay that my point of view is quite mainstream and I don’t even see it as either conservative or controversial. I don’t care what adults or even adolescents choose to see or do, but I do think that young children should be shielded from most of this.

Oct. 2, 2023 — Robert Winters
Robert Winters' Blog Now It’s My Turn To Speak

I was surprised to learn that in some public libraries there were “drag time story hour” events taking place that were publicly funded. On that same day I saw that one was taking place in Cambridge and simply made a note of this fact – and for this I was called a transphobe.

Fact: I really had never heard of such a thing – even though people apparently argue about this all the time now. In case you actually care what I think, I don’t believe it is age appropriate to subject young children to things that are either sexually provocative or overtly political. I understand that some people in Cambridge have a different point of view on such matters, but I daresay that my point of view is quite mainstream and I don’t even see it as either conservative or controversial. I don’t care what adults or even adolescents choose to see or do, but I do think that young children should be shielded from most of this.

Oct. 2, 2023 — Robert Winters
Cambridge Day Two candidates for City Council in Cambridge named as the focus of rally to ‘oppose bigotry’

“These are some pretty virulently Islamophobic, racist, transphobic tweets and likes that these candidates have put out, and the public deserves to be aware of it so that they can make an informed choice,” said DSA organizer Willow Carretero Chavez, a resident of Somerville and an undergraduate at the Massachusetts Institute of Technology.

A letter to Cambridge Day received Saturday from resident Ari Ofsevit went over much the same ground about Pasquarello and Winters, which Winters believed was a “parallel email campaign initiated by Totten to disparage me.” Carretero Chavez said the DSA had no public-facing email campaign on the topic. Separately, Totten also said he was unaware of any letter-writing campaign.

Sept. 30, 2023 — Marc Levy
Cambridge Day Two candidates for City Council in Cambridge named as the focus of rally to ‘oppose bigotry’

“These are some pretty virulently Islamophobic, racist, transphobic tweets and likes that these candidates have put out, and the public deserves to be aware of it so that they can make an informed choice,” said DSA organizer Willow Carretero Chavez, a resident of Somerville and an undergraduate at the Massachusetts Institute of Technology.

A letter to Cambridge Day received Saturday from resident Ari Ofsevit went over much the same ground about Pasquarello and Winters, which Winters believed was a “parallel email campaign initiated by Totten to disparage me.” Carretero Chavez said the DSA had no public-facing email campaign on the topic. Separately, Totten also said he was unaware of any letter-writing campaign.

Sept. 30, 2023 — Marc Levy
Cambridge Day Group should look closely at endorsed candidates and consider the company that they are keeping

[Winter's] Twitter account is a compendium of far-right ideology. None of this is a mistake, he’s liked and tweeted hundreds of racist, transphobic, anti-immigrant, anti-abortion and other vile posts over the years. (I don’t have links to every post because he seems to have scrubbed his Twitter account of some tweets.) He says he’s a registered Democrat but proudly supported Charlie Baker.

Sept. 30, 2023 — Ari Ofsevit
Cambridge Day Group should look closely at endorsed candidates and consider the company that they are keeping

[Winter's] Twitter account is a compendium of far-right ideology. None of this is a mistake, he’s liked and tweeted hundreds of racist, transphobic, anti-immigrant, anti-abortion and other vile posts over the years. (I don’t have links to every post because he seems to have scrubbed his Twitter account of some tweets.) He says he’s a registered Democrat but proudly supported Charlie Baker.

Sept. 30, 2023 — Ari Ofsevit
The Harvard Crimson Cambridge Council Candidates Clash at Forum Hosted by Harvard Grad Student Union

About halfway through the event, Aanchal Manuja, a Tufts graduate student, asked Cambridge blogger Robert Winters about several transphobic tweets he had liked.

“You have posts on Twitter that oppose trans rights, including one that calls transgenderism like a pedophilic ideology,” Manuja said.

“I actually don’t remember if I put a like or something on something I thought was funny or something,” Winters said. “That is certainly possible, but I certainly don’t remember doing anything particularly controversial in that regard.”

Manuja replied that it wasn’t just one liked tweet.

“I don’t agree with that,” said Winters.

Sept. 27, 2023 — Muskaan Arshad, Julian J. Giordano
The Harvard Crimson Cambridge Council Candidates Clash at Forum Hosted by Harvard Grad Student Union

About halfway through the event, Aanchal Manuja, a Tufts graduate student, asked Cambridge blogger Robert Winters about several transphobic tweets he had liked.

“You have posts on Twitter that oppose trans rights, including one that calls transgenderism like a pedophilic ideology,” Manuja said.

“I actually don’t remember if I put a like or something on something I thought was funny or something,” Winters said. “That is certainly possible, but I certainly don’t remember doing anything particularly controversial in that regard.”

Manuja replied that it wasn’t just one liked tweet.

“I don’t agree with that,” said Winters.

Sept. 27, 2023 — Muskaan Arshad, Julian J. Giordano

Campaign finance

See Cambridge Review for detailed information about Robert's fundraising

TBD
Raised in 2025