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The Select Board has finished interviewing three law firms vying to become Winchester’s next town counsel, with members weighing cost control, accessibility and experience as they move toward a decision.
The finalists — KP Law, Harrington Heep LLP, and Murphy, Hesse, Toomey & Lehane — each presented detailed proposals in late September and early October. Board members questioned them on how they would manage the town’s busy legal calendar, support volunteer committees, and provide guidance on complicated land-use and housing matters.
KP Law: scale and statewide experience
KP Law, the largest municipal law firm in Massachusetts, pointed in its cover letter to its roster of more than 120 cities and towns as clients. The firm described itself as “the most experienced municipal law practice in the Commonwealth,” citing a deep bench of attorneys specializing in everything from zoning and procurement to labor law and litigation.
“Municipalities today face an ever-growing array of legal challenges, and our team has the capacity to handle them efficiently and responsively,” the firm wrote.
During their Oct. 6 interview, KP Law attorneys emphasized the advantage of size, saying it allows them to provide quick, authoritative answers by drawing on subject-matter specialists. They acknowledged Winchester is sensitive to billing, but argued expertise can shorten the time needed to resolve questions.
Board members pressed them on communication, noting dozens of volunteer boards and committees often seek guidance simultaneously.
KP Law representatives said they typically work through town managers to filter requests, which keeps costs predictable and avoids duplicative work. They also offered to provide regular training sessions for boards on open meeting rules, ethics and public records law.
Harrington Heep: accessibility and land-use expertise
Harrington Heep LLP described its philosophy in its cover letter as “accessible, efficient, and practical.” Donna Brewer, who has practiced municipal law since 1998, wrote that her firm focuses on staying within budget while remaining available to both staff and board members.
The firm told the board it currently represents 17 towns and often holds weekly office hours at town halls. Brewer said such sessions allow staff and committee members to raise day-to-day legal questions without triggering multiple new billing entries.
“When we offer office hours, there is never a question those hours are well used,” she said.
Harrington Heep also stressed its land-use experience. Brewer noted recent work before the Housing Appeals Committee in contested Chapter 40B housing cases and warned that state law increasingly limits local authority.
“What we’re noticing with land use is that at the state level, the sense that it should be locally controlled is slipping,” she told the board. “We are seeing more and more statutes that reduce local authority.”
With Winchester facing several active “friendly 40B” developments, the firm said it would prioritize early staff-level coordination with developers to keep projects on track and avoid costly litigation.
Murphy, Hesse, Toomey & Lehane: labor and Town Meeting focus
Murphy, Hesse, Toomey & Lehane (MHTL) emphasized its breadth of practice and decades of experience representing municipalities across Massachusetts.
In its cover letter, the firm highlighted its strong background in labor and employment law, an area of recurring complexity for towns. It also cited experience guiding school committees and town managers through negotiations and contract disputes.
During its Oct. 6 interview, MHTL attorneys said their approach blends specialized expertise with proactive communication. They pledged to maintain close coordination with the town manager’s office to ensure requests are streamlined and costs remain manageable.
MHTL also stressed Town Meeting preparation, saying they have steered communities through difficult sessions by anticipating procedural hurdles, drafting clear motions and working closely with moderators.
What the board wants
Throughout both rounds of interviews, board members returned to the same themes: financial discipline, accessibility for staff and volunteers and the ability to guide Winchester through increasingly complex legal landscapes.
Chair Michelle Prior said she hopes to have a new counsel in place before Town Meeting begins on Nov. 3.
“We want them to be able to see how our Town Meeting operates,” she said, adding that early involvement would help build familiarity with Winchester’s legislative process.
Vice Chair Anthea Brady noted Winchester’s volunteer culture brings both opportunities and challenges.
“The town is full of volunteers who are very smart. Many of them are lawyers,” Brady said during the interviews. “We need a town counsel who can provide clear answers, keep us on budget, and help us do the people’s business effectively.”
Next steps
With the interviews and cover letter reviews complete, the Select Board will deliberate in the coming weeks. Members indicated they want a decision finalized before November Town Meeting, giving the new firm a chance to observe the proceedings before assuming full responsibilities.
For Winchester, the appointment will mark the town’s second major transition in legal representation in less than a decade. Board members said their goal is to select a counsel who can combine fiscal responsibility with the expertise needed to support a highly engaged community.
Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He previously co-founded the Marblehead Current and now runs The Marblehead Independent, a reader-funded digital newsroom.
