Sam Winickoff sat in his room, watching local politicians on a screen. It was June 2020, and Brookline was holding the first of its bi-annual Town Meetings. As he watched, the recent high school graduate could not help but notice a glaring paradox. At a time when the country was rapidly dealing with a global pandemic, a major presidential election and protests against police brutality, Brookline’s representative body was still operating slowly.
To Winickoff, the system seemed “super weird and inefficient.” Town Meeting was cumbersome; it convened only twice yearly and had so many members that most residents did not know who was who—or what was happening.
He then spoke with a friend, and they decided to take action. They built a campaign: A Better Brookline. By petitioning for a commission to create a charter—a written document that defines the government structure of a city or town—the students pushed to reexamine Brookline’s government.
Brookline’s government operates via Town Meeting, a legislative body of 255 volunteer members (TMM)—15 from each of the town’s 17 precincts. It convenes twice yearly to vote on legislation called Warrant Articles (WA), and each May, five members are elected to three-year terms.
Most Massachusetts cities elect a full-time legislative body of 7-15 councilors and a mayor. They meet much more frequently than Town Meeting.
According to Winickoff, smaller city governments are far more efficient than Town Meeting, which he said is slow and unorganized. He said city governments have a greater capacity to respond to pressing issues such as COVID-19.
Winickoff said A Better Brookline folded its efforts due to the difficulties of collecting petition signatures and the busy post-pandemic life. A similar campaign, City Charter, chaired by Precinct 3 TMM Rebecca Stone, is now reviving the students’ mission.
Stone said the campaign believes that Brookline’s size, complexity and “enormous, enormous annual budget” should raise questions about the effectiveness of its government structure. She said formal discussion is necessary to find the best path forward.
For a question of forming a charter commission to be put on the ballot, 15 percent of the town’s registered voters (approximately 6,000 people) must sign the City Charter petition.
If a vote in the May 2025 election to create a charter commission passes, the commission will develop a charter and propose it to voters in 2027. This “local constitution,” according to Stone, would propose any changes to the town government structure. By early 2028, Brookline may have a new system of government.
Brookline has never had a charter. Numerous committees have examined its government and proposed changes and bylaws, but the City Charter website notes that no “major change” has been made since Town Meeting was conceived in 1915—before women had the right to vote.
With 63,000 residents as of the 2020 Census, Brookline is the most populous town in Massachusetts. Winickoff said A Better Brookline researched surrounding municipalities and decided a more concentrated city government would better suit the town.
Precinct 7 TMM John Margolis does not support a smaller government. Margolis co-sponsored WA 18, which requested a moderator’s committee to examine Brookline’s government—a process that Stone said “doesn’t lead to a charter proposal.”
“We would have a lot fewer people directly involved in town government or city government, and it would be much less open than the process is now,” Margolis said. “People complain that the process now is not clear and open, and there’s some validity to that. A city will be much less so—much more will be done behind closed doors.”
Stone said she was frustrated by Town Meeting’s infrequent assemblies and lack of central debate. She said the slow system obstructs essential policies, and a small system would increase accountability.
Brookline’s budget for the 2025 fiscal year is $440 million, and Town Meeting is responsible for setting it. Stone said it cannot handle major decisions like budgeting and significant policies.
“Many Town Meeting members are not involved beyond being in Town Meeting. And there is no structure other than coming together as Town Meeting members to vote,” Stone said. “All of the information gathering or the research that any individual Town Meeting member does is completely voluntary.”
Town Meeting has also been criticized for its demographic, which mainly consists of older homeowners. Winickoff said a smaller structure would be more accessible to underrepresented groups. Margolis, however, said representation would not improve in a city.
“You would replace the 255-member Town Meeting with a city council of what—five, eight, nine members and a mayor?” Margolis said. “It’s just a lot fewer people. It’s going to be a lot less close to the community than what we have now. It’s just inevitable that that’s going to happen.”
In its most recent assembly, Town Meeting met three weeknights for an average of three hours a night. Another recent meeting lasted eight nights. Winickoff said the lengthy meetings and the large number of TMMs isolated Brookline politics from its voters.
“The reality is that for a lot of types of constituencies in Brookline, the people don’t have the capacity to [be involved],” Winickoff said. “If you are a single parent, if you’re working full-time, if you’re a renter, if you’re a student—these types of people are busy, and they can’t necessarily invest the time to know who those five names are on their ballot every year in May.”
City Charter continues its hunt for petition signatures, the first of many steps in a journey to change Brookline. Winickoff and Stone believe a smaller government would benefit the town by professionalizing policymaking. For Margolis, though, a city would undo the community system that has served Brookline for so long.
Winickoff said that though he sometimes felt “fatalistic” during the campaign process, the high school students, renters and long-time residents who were passionate about change fueled his efforts.
“I was really heartened by the amount of engagement that we got with our effort,” Winickoff said. “I think it sort of surprised us how many people from different walks of life – people who had never really been involved in town politics or were feeling really left out by that process – were actually interested and willing to get involved in this.”
