Politics

Notes from 75 days on the campaign trail

/ thomascallahan / Leave a comment

We decided on Friday, February 13th to pull papers to run for a seat on Milton’s Board of Assessors. Seventy-five days later we had a result. Our campaign received 2,742 votes compared to 2,095 votes for our competitor. CallahanCan turned into CallahanDid!

We pledged to have some fun with the campaign and we definitely did. What follows are notes from the campaign trail.

Stories from the doors. We hit the doors and met our neighbors all across town. Door knocking can be a grind, lots of people not home and many others not coming to the door. But the people who did answer were universally nice and we definitely received votes from neighbors who appreciated us taking the time to introduce our campaign to them. We spent plenty of time in the precincts near our home but also made a point to door knock in precincts 6, 7, 8, and 9 where we were less known. It paid off, we lost all four of those precincts but narrowly in three of the four.

Our kids. Brenna and Devan were home for the final weekend and door knocked and held signs at standouts for their dad. It was fun for me (and hopefully them) and brought me back to my first campaign for town meeting 26 years ago when they helped me win by being a cute image on a campaign flyer. This time around, they convinced neighbors to vote for me, suggested social media strategies and provided a boost in the home stretch. How great is that?

Campaign soundtrack. Brenna and Devan also suggested at least one song to our quirky campaign soundtrack – You’ll Always Find Your Way Back Home by Hannah Montana, which evidently is having a moment 17 years after its release. We also featured the offbeat – songs like “I’m a Good Dog”, staying focused on “Happy Wednesday”, “Mail Carrier March” (when our mailer hit) but used classics from Sheryl Crow, Bruce Springsteen, Queen, Sabrina Carpenter, Bachman-Turner Overdrive and others. Stay tuned for the campaign soundtrack release.

Surrounded by women. Women power political campaigns, at least the winning campaigns! And from our campaign manager, Carolyn Cahill, and campaign treasurer, Niki Boyson, to our volunteers like Katie Conlon, Sheila Dunphy and Deborah Felton, to Eileen and our daughters, women helped me win this campaign. We had our share of men too (looking at you Mike Zullas, Chris Hart, Winston Daley, and Matt Morong) but women always power our campaigns thanks to the indefatigable efforts of Judy White-Orlando, Luisa Pena-Lyons, Meghan Haggerty, Janet Ferone and so many others.

Forums. It was great to have an opportunity to reach voters in a variety of forums that took place during the campaign. A highlight was the MiltonSpeaks forum produced by Milton Access TV and featuring the Milton High School Debate Team and Milton Times. There was a forum at Fuller Village and one sponsored by the West Milton Neighborhood Association as well as the annual meet and greet at the Council on Aging. We are enormously grateful for these organizations and appreciate each of the events where we made our case directly to voters.

Endorsements. Do endorsements matter in local elections? I’m not completely sure but when you pull in support from Maritta Manning Cronin (65 years and running as town meeting member from P4); Carolyn Cahill (P1 TMM, local realtor and friend); Joe Reardon (P7 TMM and friend); and Jim Henderson (former assessor) it sure doesn’t hurt your chances. We built a campaign from the beginning that was determined to compete in every corner of Milton and the results show that we did that. Each of these endorsers put their name next to mine when they didn’t have to and I am grateful and humbled by their support.

Eileen. You can’t run a campaign alone and when you have a life partner (and secret weapon) like my wife, Eileen O’Connor Callahan, you have a invaluable campaign asset. She wouldn’t let me lose. When we were both tired, she pushed me to do a few more doors. She did all of our campaign signs and ads. She advised me on strategy and she kept me steady when a few cranks on social media took their shots (we got called a “mortgage grifter” and a “real f*cking tool”). I told people on the doors that she should be on the ballot instead of me! Thank you, Eileen.

Campaigns for these townwide positions are hard. We raised $6,600 in the most expensive race for Board of Assessors in town history, breaking the record from the 2012 race. Thank you, donors. We knocked on 750 doors personally and the campaign reached double that. Thank you, volunteers. Our mailer went to every Milton household. We lost five pounds with hundreds of thousands of steps. Thank you, doorknocking. All for the privilege of being a member of the Board of Assessors and a $125 per month stipend! Thank you, Milton.

“A republic, if you can keep it.” This Benjamin Franklin response to Elizabeth Willing Powel’s question: “Well, Doctor, what have we got, a republic or a monarchy?” resonates today. We run these local campaigns to control what we can control. At a time when our national politics are unhinged, driven by an authoritarian wannabe, we want to serve our town and our Commonwealth and move our democracy forward. Talking to neighbors, building community and encouraging everyone to vote – young and old, townie and newcomer, immigrant or native-born – is one small way we can do that.

I’m running!

/ thomascallahan / Leave a comment

Callahan for Assessor. Two months ago, I made a decision to run town-wide for the first time after thirty-one years in Milton and twenty-six years as an elected town meeting member.

The seat is open with the incumbent deciding that he would not seek reelection after twelve years of service to the Board. But it is a contested race, with another candidate having jumped in.

Why run for a seat on the Board of Assessors? The idea first came to me when I was elected to serve as a Trustee of The Appraisal Foundation, where I served from 2010-2015. I currently volunteer as a representative to the Foundation’s Council to Advance Residential Equity (CARE). The Foundation is congressionally authorized to enact standards and qualifications for real property appraisers in the United States, and CARE provides input to its boards through a fair housing, consumer advocacy and civil rights lens.

Milton employs two professional appraisers and my experience with The Appraisal Foundation over the last fifteen years gives me a unique understanding of the standards, practices, and responsibilities that underpin this work. That experience has prepared me well to serve effectively on the Board of Assessors.

I briefly consider a race two years ago and again last year when a friend challenged a longtime incumbent and narrowly lost. This time, the open seat was too attractive to pass up. I’m in the race.

While I’ve run issue campaigns before in Boston and in Milton and assisted many friends who have run for office, running townwide is different. It takes a higher level of energy and resources. I have been truly humbled with the number of family and friends, inside and outside of Milton, who have donated, taken a lawn sign and offered to doorknock with me. Regardless of outcome, I am grateful that so many people have joined the effort.

Boards of Assessors have a serious responsibility to ensure that properties in town are assessed fairly and equitably. Fairness and equity have been at the center of my career. They hear requests from residents for tax abatements and hardship deferrals. It is an important role, and if elected, I will focus on increasing transparency, modernizing processes, and improving communication with taxpayers and other town departments. We will actively connect older adults with tax-saving programs that help them remain in Milton.

I will draw on my experience in Milton’s town government, including my service on the Affordable Housing Trust and as Chair of the Community Preservation Committee, to help residents better understand the role the Assessing Department plays in our community. I will draw on my role volunteering as a coach, PTO member, parishioner, and neighbor.

If you’re able, please help us reach the voters we will need to win this race. With Election Day less than 20 days away, I’m grateful to everyone helping us sprint to the finish line. Visit our website to read more and make a donation.

Donate to Callahan for Assessor

Deja vu? Non, merci!

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Yogi Berra famously said, it’s like “deja vu all over again”. Yes, I’m a Yankee fan but even diehard Red Sox fans can agree that deja vu all over again befits the situation in Milton perfectly.

It has been eighteen months to the day since Milton’s town clerk certified signatures to place a question on the ballot seeking to overturn a town meeting vote for the first time in over 50 years. That effort succeeded after a brutal campaign featuring outrageous claims by the forces of “no”. Those claims –from the state won’t sue Milton to we won’t lose any state grants – have proven to be false.

Our intrepid band of NIMBYs kept battling against the odds. Like a gambler at a casino who keeps thinking the next hand will turn the tide, they keep losing and losing big. Today, they lost again…big. Sixteen residents filed suit challenging Milton’s designation as a rapid transit community and, by extension, our requirement to zone for 2,461 units. Just a week ago, they said this was their big chance. A favorable judge, they said. A first chance at “adjudicating” the trolley as rapid transit argument, they said.

“Nope” said the court. The courts have said no all along the way. The legislature has refused to consider amendments to water down the law. The state’s Executive Office of Housing and Livable Communities has been steadfast. A local attorney that wanted the town to file a similar claim declined to take on the case after realizing the Select Board intended to follow the law and the lead of town meeting and submit the newly passed zoning plan to the state for approval.

Milton’s new zoning amendment fully complies with state law. And leaves East Milton, the neighborhood which voted in large majorities to reject the 2023 zoning, largely out of the plan. It is, in many respects, a better plan. A better plan from a planning perspective and a better plan politically.

But Denny Swenson and her acolytes began gathering signatures in earnest on Monday in another attempt to repeal the latest compliant zoning plan passed by town meeting. Deja vu. They can’t win in a forum made up of 279 elected town meeting representatives dominated by well-informed residents. But they proved last February they can win with a well-funded campaign featuring lies, fear and exaggeration. So they attempted to try again.

But you can never exactly recreate the same political environment. Many voters move on. Anger subsides. And towns do face real consequences for ignoring a state law.

Today’s 5pm deadline for signatures came and went and no signatures were filed. Organizers haven’t made a public statement yet but they undoubtedly struggled to reach the required 1,100 signatures need to put this before voters. They definitely had less volunteers this time around. There is anecdotal evidence of better-informed voters declining to sign the petition.

Whatever the reason, the outcome is good for Milton. Inclusivity won. Milton becomes community #139 to comply with a state upzoning law that will not solve our housing crisis, but will become part of a long-term strategy to make our all of our communities a bit more welcoming.

Yogi might say, “it ain’t over ’til it’s over.” Last ditch legal strategies will continue. Political posturing will continue.

But, it is over.

Friday Night News Dump

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News out of Milton tonight is that a local elected official has filed public comments on the MBTA Communities Act regulations. Ok, that elected official is me! What else would one do on a Friday night in between snow events?

As a Milton resident and elected town meeting member for the past twenty-five years, I write to offer the following comments on MBTA Communities Act regulations.

The updated definition of “Subway station” to include any of the stops along the MBTA Red Line, Green Line, Orange Line, or Blue Line, including but not limited to the Mattapan High Speed Line and any extensions to such lines is a welcome clarification. Our Mattapan trolley fits any reasonable definition of rapid transit because it runs on a frequent and regular schedule and operates on an exclusive right-of-way. Nevertheless, it has been the target of many opponents of this law, drawing much scorn and ridicule as a broken down relic.

Most of those critics in our town don’t ride the trolley. As an occasional rider on the Mattapan trolley, I am able to commute from Milton to downtown Boston in less time than it takes embarking from some of the stops on the Green Line. This dedicated transit line is a valuable resource to Milton residents (as well as Mattapan and Dorchester residents) and clearly qualifies as a subway station for the purposes of this law which is designed to create multi-family housing opportunities close to jobs and transit. The trolley is old and occasionally cranky but it is notable that the MBTA has clear plans to upgrade the trolleys and the line in the coming years. According to the MBTA’s website, over the next eight to 10 years, they will modernize stations and improve infrastructure throughout the Mattapan Line. This includes introducing the next generation of vehicles to the line, the Type 9 light rail vehicles used on the Green Line. Milton is a rapid transit community now and will remain one in the future and should be treated as such under these regulations.

The requirement that Milton and other rapid transit communities create a zoning plan allowing for Multi-family unit capacity equal to or greater than 25% of total housing units is reasonable, especially when you consider that build-out will take many decades and towns may never reach the upper limit of that zoning capacity. Milton must do its part to create housing opportunities in a state where it is increasing hard to afford rents or home prices. Housing supply is vital to our economic health as a town, region and state.

I applaud the provision of the regulations that permits the Executive Office of Housing and Livable Communities, in its discretion, to allow towns to approve a greater percentage of affordable units, or deeper affordability for some or all of the affordable units, if it meets certain conditions. Those conditions are necessary so that so that towns don’t attempt to “game” the system by requiring an affordability percentage that ensures no multi-family housing gets built. But it also allows towns like Milton, where the market is strong, to exceed the 10% affordability requirement and provide more opportunities to low- to moderate-income residents. In fact, this was one of the few areas of agreement between the “yes” and “no” campaigns during last year’s town-wide referendum on the zoning plan passed by Milton town meeting in December 2023. Thank you for providing this important flexibility in the regulations.

Additional flexibility is shown in the regulations by allowing certain communities, including Milton, to craft a Multi-family zoning district with at least 50 percent of the district’s minimum Multi-family unit capacity located within the Transit station area while the remaining capacity can be elsewhere in town. As you know, this was a crucial nod to the Town of Milton since our trolley line is adjacent to Boston and much of our zoning capacity would otherwise be in Boston and not eligible for rezoning by the Town of Milton. I appreciate the state listening to town officials and incorporating this flexibility into the regulations. One size does not fit all and this flexibility is a necessary and welcome relief to communities that have unique circumstances like a trolley line on the town’s border.

My final comment concerns the deadlines that apply to Milton. February 13, 2025 is Milton’s deadline to submit an action plan and July 14, 2025 is our deadline to submit a District Compliance Application. Our town has had several years to comply. Some of our elected officials have not used that time wisely. Certain elected officials in Milton have chosen to litigate instead of legislate. Other communities (117 as of this writing) have chosen to comply and the state should not allow Milton to further delay full compliance. Milton has had enough time to come up with a plan. Now Milton needs to be compelled to do so.