Notes from 75 days on the campaign trail

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!

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.

If Bedford Falls had community reinvestment…

New York was the first to pass a state-level Community Reinvestment Act. What would have happened to fictional Bedford Falls (many believe modeled after Seneca Falls, NY) if CRA had been in place in the post World War II era?

You know the Community Reinvestment Act. Signed into law in 1977 by President Jimmy Carter after being championed by Senator William Proxmire (D-Wisconsin), it became one of the last civil rights-era laws passed before the Reagan revolution upended modern politics. It followed on the footsteps of the Equal Credit Opportunity Act (1974) and Fair Housing Act (1968) and other measures designed to end discrimination and rollback policies like redlining. The law states simply that federal regulators “…shall assess the institution’s record of meeting the credit needs of its entire community, including low- and moderate-income neighborhoods, consistent with the safe and sound operation of such institution.”

And most of us know the timeless movie It’s A Wonderful Life starring Jimmy Stewart as everyman George Bailey and Lionel Barrymore as the evil banker, Mr. Potter. George as the head of the Bailey Building & Loan who has provided substantial opportunity to the town’s “rabble” in the form of home loans and personal loans presumably not available at the more traditional banking institutions in town. Potter runs an apparently unnamed bank in Bedford Falls and has designs on complete control of the local economy and sees the Bailey Building & Loan as an obstacle.

Let’s speculate a bit and put the Community Reinvestment Act in play here. When George needs help from the other banker in town, he might have offered Mr. Potter a deal that would have earned Potter’s bank considerable Community Reinvestment Act credit. The Bailey Building & Loan was serving the area’s low- to moderate-income residents. George helped the Italian immigrant Giuseppe Martini and his wife buy a home in Bailey Park at a time when Italian-American discrimination was still widespread. He lent George Bishop $5,000 to buy his home so he could “work and pay and live and die in a couple of decent rooms and a bath.”

Who knows? If the movie had continued, would it have been shocking to see Annie, the film’s only Black character with a speaking role, finance a home with a loan from the Bailey’s?

And those pesky bank examiners paying a visit to the Bailey Building & Loan on Christmas Eve? They would likely have been asking Mr. Potter what investments his bank had made in housing and financing the “lazy, discontented rabble” he liked to rail against.

George would have needed the capital that only Potter’s bank could have provided to build out Bailey Park and offer more homeownership opportunities to town residents. Bedford Falls might have welcomed a diverse group of WWII veterans returning home looking to join the growing ranks of the middle class and achieve the American Dream. A CRA in that era might have been just the ticket needed to redeem Mr. Potter and provide a model for those looking to create opportunities for the 1.2 million returning Black veterans that ended up being stymied by the racist implementation of the GI Bill.

Every movie needs a villain but our communities do not. It’s A Wonderful Life without the Potter-Bailey feud would likely make for a less memorable film. But set in the CRA-era, it would be truly wonderful to see what a partnership between George Bailey and Henry Potter could have meant for Bedford Falls. No angels needed.

Guilty!

It was a quiet summer in Milton. On Monday, MA Lieutenant Governor Kim Driscoll came to town for a groundbreaking of a 92 unit mixed income apartment building in a formerly under-utilized parcel behind the main business district in East Milton Square. I attended the groundbreaking and then later posted about it on the two main Facebook pages in town – Milton Neighbors and Everything Milton.

Oh boy. The comments flowed…illiberally.

“This is not progress at all, it is destruction of a wonderful neighborhood and it is wrong.”

“And up go the projects.”

“More migrants waited on hand and foot.”

“Can’t wait for the hookers and crack addicts..”

“Mr. Callahan is so happy to destroy a nice town.”

Guilty as charged?! I am happy that this development is moving forward. I’m also happy that the 52 unit Ice House condominiums on the other side (my side) of town are being sold and occupied. Thirteen of the homes will be sold to low-to moderate-income first-time buyers later this summer and fall. I’m happy that we are finally in compliance with the state laws on MBTA Communities and accessory dwelling units.

What the haters fail to appreciate is that new homes will not destroy Milton but rather they will make us a better town. Milton is not on its way to becoming a “city” as many have voiced. But the next generation may have a chance to live in this “nice town” if we continue to add a diverse mix of homes at various price points.

I’m happy our young family chose to move to Milton thirty years ago. I’m happy that we have stayed long after our children have grown up and out. Milton is a nice town (those Facebook comments notwithstanding) and I’m happy that so many of our neighbors work so hard to make sure Milton welcomes neighbors, new and old alike. Find me guilty of that!

A consensus on housing in Milton?

Can we talk about another housing issue in Milton that has the potential to bring residents together. Town farm. In 1701, Royal Governor Stoughton deeded his 40 acre wood lot to benefit the town’s poor. Today, only 4 acres remain and many in town believe affordable housing is the best way to honor the will. In 2023, Governor Stoughton Trustees (who double as Select Board members) issued a request for proposals for thirty-five units of affordable housing on the site. But a change in control of the Select Board in spring 2024 meant the responses to that RFP were put on hold.

A Town Farm review committee was set up in July 2024 and didn’t meet until January 2025. When we did (yes, I managed to get appointed to this committee), we held a public forum to hear ideas for the site from residents.

While there is a wide range of opinions among committee members and town residents, I believe there is a strong consensus forming in town that the remaining four acres of one of the last remaining poor farms should include permanently affordable housing. What that housing looks like, how many units, and who should live there are all questions where there isn’t full agreement. But most residents seem to agree that housing for the “poor” is part of the history of the site dating back to 1805 and should be part of its future.

Our committee heard from many Milton residents who support that position. Fully forty of the fifty-five commenters supported some form of affordable housing on the site. Some said it should be senior housing. Some preferred rental housing while others pressed for homeownership. We heard from residents about a “Home Inc” style development featuring townhouses while many commented positively on the farmhouse style design reusing existing buildings featured in one of two RFP responses. A dozen commenters opposed affordable housing on the site and another three expressed other concerns.

We listened to several ideas about alternative uses and heard creative proposals around a public farm to support the Milton Food Pantry, a non-profit animal shelter for people that need to find a home for their pet while they work toward stable housing, an organic farm/beehive, and hybrid ideas such as a land trust or co-housing, food forest, environmental education park, childcare facility, nonprofit incubator, or veterans housing. We heard from some that the land should be sold, similar to the 30 acres on Woodlot Drive, to a developer to build market-rate homes and the interest on the proceeds used to increase support for the Food Pantry and Milton Residents Fund.

The Governor Stoughton Trustees should move swiftly to pursue a plan for the site that prioritizes the creation of affordable housing held in perpetuity. This site has been a political football for far too long. Serious debate about the future of Town Farm began over twenty years ago. In 2011, the town sold 30 acres to Pulte Homes but left the remaining four acres for future Trustees to decide.

We have a chance to save one of the last remaining poor farms in New England and now is the time to do it. Both neighbors, and the town as a whole, deserve certainty about the future of this historic piece of land. Governor Stoughton Trustees should open a conversation with the Milton-based development team that responded to the RFP to see what is possible on this important site. The Homes at Stoughton Farms, as Milton resident Ralph Parent has proposed, would honor the past and provide for a future of this site that would make Milton proud.

Deja vu? Non, merci!

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.

The Pope and the Plan

On May 8, 2025 two momentous events happened. In Rome, the College of Cardinals elected an American Pope. Minutes before the white smoke appeared Vatican experts were on television saying it would never happen. And then it did.

Later that evening in Milton, our Planning Board voted to advance a zoning plan that met the state’s requirements for our town after many of us saying that it would never happen. I believe I heard church bells ringing in town, perhaps celebrating both votes!

While Pope Leo XIV celebrates a week on the job, Milton’s compliant zoning plan didn’t make it that far. On May 13th, our Planning Board took a highly unusual step and rescinded its vote, deciding to advance another plan that is out of compliance with the state law and zones for 60% less housing than the state has required.

Pray for us.

The now-rescinded plan would have brought us into compliance, sparing East Milton residents who voted overwhelmingly against the previous plan in 2024, and creating multi-family zoning districts in more neighborhoods in West Milton. It is not a perfect plan but it is a good, thoughtful plan crafted by Planning Board member Cheryl Tougias (the lone voice of compliance on our Planning Board) and the town’s expert consultants from Utile.

What comes next is anyone’s guess. Milton is at risk of missing yet another state deadline. And being sued once again. And continuing to lose out on state grants, the latest being the loss of a grant for a van for our Council on Aging. Outgoing Select Board member Erin Bradley tallied the total cost to Milton so far as over $1.1 million in legal fees and lost grants.

Pray for us now.

There is hope beyond the prayers. While two incumbents were returned to the Planning Board, two new members were elected to the Select Board and a new Town Moderator was elected as well. Town Meeting is strongly in favor of following the law. But zoning articles must pass through the Planning Board and four of the five members seem to be doing everything in their power to avoid our responsibility to follow a state mandate.

Pray for us.

Pray for a kind and benevolent special master appointed by the Attorney General if we continue to resist. Pray for state officials with short memories when we do eventually comply and the state evaluates funding requests from Milton for vans, schools, public safety, and more. And pray for our neighbors who need more housing options in a town that hasn’t grown in over fifty years. Our population in 1970 was 27,190; today it is 28,811 – a 0.1% annual growth rate. For comparison, neighboring Canton has grown by over 7,000 residents in that time; Sharon over 6,000.

An American Pope and a compliant zoning plan turned out to be too much to expect in one day. But Rome wasn’t built in a day. Milton will be in compliance, consistent with being a rapid transit community. It will be a day in the future. And it will be a day!

Send it back

Two nights of town meeting and two nights of dysfunction. Milton has been renamed Dysfunction Junction (with several rapid transit stations naturally!).

Last night, we sent two articles back to the Planning Board for more work including one on Accessory Dwelling Units. State law mandates ADUs in single-family districts now but towns can place “reasonable” restrictions on them. Town meeting determined that the article before us was not reasonable, including requiring more of those who wish to add a 900 square foot ADU than those wanting to build a 5,000 square foot McMansion. It was sent back for more work.

A site plan review article was sent back to the Planning Board. Two other articles were sent back to the Select Board. Town meeting members sent back 4 of 13 articles that were initiated by town bodies.

We did close town meeting with a bang however. Debate on Articles 14 and 15 came late, going until 11:15pm. Article 14 was a citizens petition to transfer $24.61 (a penny for every zoned unit called for by the MBTA CA) from the town’s legal budget to the schools. A symbolic shot across the bow of a town that is paying lawyers $940 per hour to defend us against the Attorney General. Article 15 was a non-binding citizens petition signed by over 200 residents that asked for the Planning Board to do its job and comply with the MBTA Communities Act.

The debate was fiery. Sad. Disquieting. Three leaders of the “no” campaign took to the floor to double-down. The loss for the town in the Supreme Judicial Court was actually a win. Their greatest hits were played again. The no side really does want more affordable housing. The yes side doesn’t listen. Rapid transit is not rapid enough. It was angry, rambling and at times unhinged. Our moderator interrupted a town meeting member and reminded him to “not cast aspersions” but relented when the speaker told him he was casting aspersions on state government. That’s okay I guess. A heckler saying the “whole game is rigged” in a Trump-like rant from the cheap seats. The lead “no” organizer doing a commercial for her political operation. And the advertising executive turned affordable housing expert railing away and lying to the body by saying, three times for effect, “there is no provision for affordable housing in the MBTA Communities Act.” There is.

Not a great night. One hopeful sign was the overwhelming support for our public schools over the two nights. Both articles addressing our school overcrowding passed with huge majorities. We will need that unity this spring as Milton will vote on an override to stave off job cuts for our teachers and public safety personnel. Our divide on housing is real and deep. Our next test is to come together in support of a yes for our schools and town government services amidst the national anti-government environment. Godspeed, Milton.

Milton and smallpox

A break, of sorts, from housing politics (although more coming on that soon). I learned this morning from Milton Historical Commission members Meredith Hall and Steve O’Donnell that the town of Milton became part of the first municipal effort in the United States to offer free vaccination to residents as part of the early efforts to eradicate smallpox. This excellent article on the website of the National Museum of American History details the role of Milton and its residents.

“Over three hundred persons were inoculated during a three-day campaign in July. Following this program, the town leaders took an unusual step—they decided to hold a public demonstration to prove without a doubt that cowpox vaccine offered protection from smallpox. On October 9, 1809, twelve children, selected from those vaccinated in July, were inoculated with fresh, virulent smallpox matter by Dr. Amos Holbrook and witnessed by eighteen town members. The children were confined to a single home for fifteen days and on October 25 were discharged with no sign of smallpox infection.”

“In 1810 the State of Massachusetts passed the Cow Pox Act directing every town, district, or plantation, within the Commonwealth, to provide for the vaccination of their inhabitants. The world is now free of small pox—a remarkable global achievement that owes a small debt to the citizens in a little town in New England in the early years of our republic.”

Why were we talking about smallpox this morning? It came up on a site walk organized by the Town Farm review committee charged with making a recommendation for the future use of the historic poor farm deeded to the town in 1701 by Royal Governor William Stoughton. We walked past the 1888 “pest house” which was used to quarantine people with infectious diseases. Pest houses were alternately called plague houses, fever sheds, or pestilence houses.

About twenty-five Milton residents braved the cold temperatures this morning to learn more about the site and its history of providing housing for the town’s poor. Three structures from the 19th century – the main almshouse, men’s almshouse along with the pest house – still remain although in very bad condition. Two developers have responded to the town’s Request for Proposals with plans to build 35 units of affordable housing on the site respecting the historic nature of the site. I did say a break, of sorts!

Tired

“I get up in the evenin’
And I ain’t got nothin’ to say
I come home in the mornin’
I go to bed feelin’ the same way
I ain’t nothin’ but tired
Man, I’m just tired and bored with myself…”
– Bruce Springsteen, Dancing in the Dark lyrics

Tired. Last night, Milton’s Select Board voted 3-2 (sound familiar?) to submit a tired letter to the state commenting on the new MBTA Communities Act regulations. Four years after its passage and after two full years of vigorous debate and opposition to this “massive state overreach”, our Select Board filed a letter taking exception to exactly one provision of this state law – our trolley is not rapid transit, they said.

The letter conveniently ignores that Chelsea, served by no subway lines but rather Silver Line dedicated bus route, is also considered rapid transit. The letter also cites the “abandonment” of a project in 1968 that would have extended the Ashmont branch to Mattapan using the trolley right-of-way and Red Line subway cars. That project was, of course, abandoned after vigorous protests from Milton residents.

Our current Select Board majority is “tired”, even “sick and tired”, of hearing about how we were “classist and racist”. We should stick to history and fact, they say.

Here are some facts and some history. 177 communities have been asked to comply with a 2021 upzoning mandate by the state with one of the worst housing affordability problems in the nation. 118 have submitted compliant zoning plans in good faith; 26 of 30 communities submitted action plans by February 13 stating an intention to comply with the revised state deadline of July 14, 2025 (the remaining small towns under 7,000 people have until Dec 31, 2025 to submit plans).

Four communities, Milton included, decided to remain in the increasingly lonely space of non-compliance. Defiantly non-compliant. And tired. Milton’s opposition is increasingly tired after each successive loss we endure. Losing at the game of “she won’t sue us”. Losing state grants. Losing legal fees. Losing at the state Supreme Judicial Court. And now losing with the vast majority of our peers who are complying with the law.

Milton has a long history suing the state. Milton vs. MBTA in 1968 tried to stop the replacement of the trolleys with subway cars. Milton residents at the time argued that there was “no apparent transportation benefit to the proposal” to replace the trolley with subway cars. Now, we argue that the trolleys are so inferior to other transit options that our zoning requirement should be slashed by 60% or even 80%. Our “unique” town is on an unenviable, and costly, losing streak. And that is tiring.