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.
