scorecardresearch Skip to main content

In a storied sideline run, Milton Academy’s Kevin MacDonald has put present and future of his players first

Entering his 27th and final season, Kevin MacDonald is 138-60-3 at Milton Academy, but 237-101-5 overall including his 14 seasons as head coach at Archbishop Williams.Jim Davis/Globe Staff

When Kevin MacDonald walks the sideline Saturday in the first game of his final season at Milton Academy, the players and coaches beside him will serve as a testament to his commitment.

The veteran football coach and teacher — who was at Archbishop Williams for 19 years (14 as the helm) and the last 26 years as the head coach at Milton Academy — has helped countless student-athletes reach their goals on and off the field over those 45 years. He’s impacted so many lives that nearly his entire coaching staff is comprised of former players from those two stops, including his successor, Mike Mason, who has spent the past 33 years as his assistant after playing linebacker for MacDonald at Archies from 1982-86.


Playing for Coach Mac in his final season means everything for us

“The coaching staff has been around for years, and that’s a testament to [MacDonald],” said Mason, a Milton police officer, who has been the Mustangs defensive coordinator the past 15 years.

“He’s just so committed to the kids, and he’s been a huge influence in my life. I’ve been with him since I was 14, so he’s almost like a second father to me.”

With a career record of 237-101-5 (138-60-3 at Milton Academy), MacDonald has the sixth-most wins among active coaches in Massachusetts. The English and physical education teacher has led Milton Academy to seven Independent School League titles, including undefeated ISL seasons in 2019 and 2021. He also directed Archies to seven Catholic Central League titles, three Super Bowl appearances, and a state title, earning an induction into the Massachusetts High School Football Coaches Association Hall of Fame in 2013.

Senior quarterback Jake Holtschlag will be one of 13 starters returning from last year's Milton Academy football team.Jim Davis/Globe Staff

This season, the Mustangs return 13 starters, led by senior quarterback Jake Holtschlag, Penn State-bound tight end Andrew Rappleyea, defensive end Jack Crowley, and wide receiver Ben Waterman. They open Saturday night at 7 under the lights at Milton High against a powerhouse BB&N program.


The 67-year-old MacDonald has seen the ISL change drastically in 26 years, with former BB&N coach John Papas spearheading an aggressive recruitment campaign that raised the level of play in the private school league, eventually generating more interest from Power Five colleges.

“The whole complexion of the ISL has changed,” said MacDonald. “It used to be a good league, and now it’s a really good league with a lot of great players. John Papas had a lot to do with that. He really recruited hard and forced everybody else to follow suit if they wanted to compete.”

“When I first came here you’d see maybe 15 college coaches in the course of a year. Now we’re seeing over 200 coaches visit in a season.”

While he plans to step down due to health issues (he was diagnosed with Parkinson’s disease three years ago), MacDonald will remain committed throughout the college placement process for each of his current players.

After living on campus for over two decades, he will retire to his Cape Cod home along with his wife, Tracy, who has taught at Silver Lake for 20-plus years. His daughters, Jacquie (a three-sport coach at Chauncey Hall), Molly (a lacrosse and field hockey coach at Lawrence Academy), and Amy (JV girls’ basketball coach at Dartmouth High) will continue his coaching legacy.

The football lifer — who once played at Wellesley and Holy Cross — plans to stay involved with his sport as a local assistant coach, or by working independently with student-athletes in their college placement process.


“Coach Mac is the best at the whole recruiting process,” said former Milton Academy quarterback Jake Willcox, who passed for 356 yards and three touchdowns in his first start at Brown last Saturday.

“The guy knows everybody, and he doesn’t hesitate to get on the phone. He’s very sincere, and he pours everything he has into it. He loves teaching, loves football, and he really does give it 100 percent.”

Since MacDonald is admittedly not technologically intuitive, he gets help with some of his younger assistants — led by JV basketball coach and assistant Scott Prince — when it comes to the social media aspects of the recruitment process.

And MacDonald handles the more interpersonal aspects of recruiting in a “perfect blend of old school and new school,” Willcox added.

“I’ve found over the years that we can find a college for everybody,” MacDonald said. “They don’t have to be superstar players. It might not be Notre Dame or Michigan, but if you work hard with academics, we can definitely find a fit.”

As he prepares to leave his position, MacDonald said he’s extremely relieved that the school hired Mason, keeping his familiar staff in place instead of opening up a nationwide search for a new coach.

Members of his coaching tree have branched out to their own gigs, such as current Hanover coach Chris Landolfi, his brother Matt Landolfi (Duxbury), Stephen Aborn (Pembroke), and former Silver Lake coach Chris DiGiacomo.


Archies graduate Paul Healey (’77), who died three years ago, was another mainstay on MacDonald’s staffs for 31 years.

Many more assistants have stayed on with “Coach Mac,” a sign of encouragement for the players who are preparing for the upcoming varsity season, and those who are just beginning their journey at Milton Academy.

“Playing for Coach Mac in his final season means everything for us,” said Holtschlag, a 6-foot-4-inch, 210-pound passer headed for Georgetown.

“He’s worked so hard, and cares so deeply about every Milton Academy player past and present, which shows in the fact that a lot of his players come back to coach with him. The program is in excellent hands with coach Mason and I firmly believe he’ll continue the legacy that Coach Mac established.”

Milton Academy’s head football coach Kevin MacDonald, 67, will be retiring at season's end. But his impact on the program and his players will be his lasting legacy. "Playing for Coach Mac in his final season means everything for us,” said quarterback Jake Holtschlag, a 6-foot-4-inch, 210-pounder headed for Georgetown.Jim Davis/Globe Staff