Events St. Patricks Day

Michael MacDonald, Esq., Recipient of Hillcrest Educational Foundation’s 2019 “Judge John A. Barry Community Service Award”

Name: Michael “Mike” MacDonald, Esq.
Award: Judge John A. Barry Community Service Award
Occupation: Attorney
Other Positions: Member of the Windsor Finance Committee; Past President of the Berkshire Theatre Group; Vice President Board of Trustees for the Colonial Theatre Association; Past; President and Board Member of Downtown Pittsfield, Inc.; President of Downtown Investment Company, Inc.; Community Turf Field Committee; Past Chair Windsor Planning Board, Co-Founder and Assistant Coach, Pittsfield Lacrosse Club

When Michael “Mike” MacDonald started to hit his stride in his career as an attorney in his 40s, he questioned whether to continue living in Berkshire County.

“When I hit 40…North Street was dead. You could roll a bowling ball down North Street at 5 o’clock,” Mike said. “And I really considered, you know, I’m coming into my top earning years as a lawyer, maybe this isn’t the place for me to be. Maybe I should move back down towards Springfield or Boston. Or someplace like that.”

He continued, “And then as I thought about it more, I [realized] I could go to those places, I could start over in terms of reputation…and I can’t have the impact there that I might be able to have here. And I didn’t know what that meant in terms of the kinds of things I’d be involved in, but I made the conscious choice to stay here and be involved.”

Downtown Pittsfield & The Colonial Theater
Berkshire County is lucky he did! At this point, Mike was already involved in Downtown, Inc., which he joined in 1984 and would remain a part of until 2010, spending 3 or 4 years of that time as president.

From there, Mike’s volunteer work continued to grow. He says it’s the link that got him involved in the Colonial Theater, Central Block, Beacon Theater, and Capitol Square. Referencing the work he did to negotiate and lead the merger of the Colonial Theatre Association with the Berkshire Theatre Festival, he says it was a “monster of a project.”

“When we started, and as I said this was a team effort, we hired some folks to come, some professional fundraisers, who said, ‘You might be able to raise 6, maybe 8 million dollars.’ And we knew that wasn’t going to be near enough to do the whole project. Then just a whole lot of lucky breaks, really,” he said, describing the creation of historic state tax credits, the creation of Federal New Market Tax Credits, and buying the warehouse that is now the lobby on back of house from the Raser family.

“It was a $23 million project. …[I]f you told me in the beginning that it would be $23 million, I would have said, ‘I’m out of here. I’m wasting my time.’ But by then we were in so far that there was just no giving up.”

Turf Field
At the moment, Mike’s finishing up the turf field project he and the rest of the Community Turf Field Committee have been working on for the past 7 years.

He describes a lot of obstacles that turned what he believed to be a 6-month project into a 7-year project, but the results have made the hard work worth it as the field has quickly become a staple in the community. “Virtually, from the day we opened on Labor Day weekend to the day the snow blew in in mid-November, it was used most days on multiple occasions, and on every day but three.”

There are a few finishing touches the team wants to implement, including larger ADA-compliant stadium seats, concession stands, and drainage on the sidewalks. Mike adds, “We’d like to also do some ticket booths, which we hadn’t thought of, but watching the poor mothers and volunteers at the games sitting at a fold-out table…we thought ‘Oh we better…’”

Remembering his Mentors
Though he’s been involved in a number of big projects over the years, Mike doesn’t forget about the people who inspired him to get involved and pay it forward. He’s been fortunate enough to have not one, but several extremely influential people in his life who have helped and inspired him to get where he is today.

“There was a very important lady in my life growing up who was doctor when women weren’t doctors. We mowed her lawn and took care of her house. She was never married. And she encouraged me to go to school and gave me a bit of financial help,” Mike said. “[She] told me a story about how…a woman in her town in Amherst had encouraged her to to go school and helped her financially with the promise that she’d pay it forward. So I’ve made [the] same promise, which I’ve kept in terms of helping people with school, but also was just the idea of recognizing when you’ve been lucky and being willing to give back.”

In 1981, he began working for Jeff Cook, an attorney “involved in just about everything.” Jeff quickly became Mike’s mentor and encouraged him along with his young colleagues to similarly be involved. Jeff’s example as a community servant inspired Mike to get involved and make a difference.

For the Future
In terms of the future for the Berkshires, Mike would love to see it continue on the path that it’s been on. Pittsfield used to be referred to as the “the hole in the doughnut. You go to South County for cultural events, go to North County for cultural events. Drive through Pittsfield.”

Now, he’s thrilled to see the kind of activity commonly seen on North Street.  “I think back to when I first got involved in downtown Pittsfield. If you had told me that we would have as many liquor licenses and restaurants [as we do], two live performing arts venues, a multiplex movie theater, I’d have said, ‘You’re crazy.’”

When he first got started in 1982, they were knocking on landlord’s doors asking them to spruce up the appearance of the ground floor by painting window sills and picking up garbage. The landlords told them that rent barely covered mortgage and insurance, never mind cosmetic fixes.

Looking back at where he started, he’s thrilled with Pittsfield’s current “hustle and bustle” and hopes to see the same kind of economic growth in the coming years. And with the people we have here in the Berkshires, he’s confident that growth will continue.

“Every one of these projects, it takes a lot of people, a lot of perseverance, and in the Berkshires…there’s [an] incredible generosity of spirit. An incredible volunteerism. A lot of time you see the same faces, but they don’t give up. So it’s a cool place to be.”


Mike’s dedication to Berkshire County is inspiring to all of us here at Hillcrest Educational Foundation. We could not be more honored to be present him with our “Judge John A. Barry Community Service” award.  

Please join us in celebrating Mike on March 27, 2019, at our Robert “Bees” Prendergast St. Patrick’s Reception. We’ll enjoy cocktails, heavy hors d’oeuvres, a full online auction with bidding through text messages, and live music.

RSVP here by March 21, 2019. See you there!

1 comment on “Michael MacDonald, Esq., Recipient of Hillcrest Educational Foundation’s 2019 “Judge John A. Barry Community Service Award”

  1. Pingback: Hillcrest Educational Foundation Raises $$$$ at the 2019 Robert “Bees” Prendergast St. Patrick’s Reception – Hillcrest Educational Foundation

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: