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Kevin Macdonald, Athletic Department, 1996–2023

Kevin Macdonald, Athletic Department, 1996–2023

During the fall season, as the early morning sun rises over the Quad on any given Saturday, you could always see Kevin Macdonald’s minivan parked in its usual spot on Chapel Hill. It was game day, and if you were looking for Coach Mac, you would not find him in his office or in the film room. You would most likely find him in the basement of the RSG filling up 50 water bottles in preparation for the game.

One might ask, why didn’t he save this task for his managers, or assistant coaches? Why is the head football coach, who has won nine ISL Championships, three New England Championships—including six undefeated seasons—filling up his team’s water bottles on game day? The answer is that this is one of the many rituals, or some might say superstitions, that Kevin would perform every game day. Other superstitions included wearing the same faded tight blue t-shirt every Saturday during a win streak, or when he would not allow Coach Rebuck to ride the team bus to any away games, because the last time he did, the team lost.

Like most coaches, his game-day superstitions and routines have not changed during his amazing 42-year coaching career. At the young age of 22, Kevin started his coaching journey at Archbishop Williams where he amassed an incredible 99-41-2 record, which included seven Catholic Central League Championships, a Super Bowl Championship and numerous Boston Globe and Massachusetts State Coach Of The Year Awards. While at Archies, he also taught English, where he met a particular colleague who became his best friend and his future wife, Tracy.

Soon after their marriage, their three daughters, Jackie, Molly and Amy, were born. Not only were the athletic genes passed down to all three, but also the teaching and coaching genes are now fully engaged as they are all currently, or recently, teaching and coaching at the secondary school level. Clearly, the next generation of the Macdonald Coaching Alliance is strong.

In 1996, Kevin decided to pursue a new position and in August he was hired as the new head football coach at Milton Academy. Along with his coaching duties, he taught a variety of Physical Education classes and also coached hockey and baseball. Later, he was able to also teach one of his favorite subjects, Expository Writing, known for many years as “Expo.” Although Kevin had some trouble adapting to new technology during his later years (just ask Mark Connolly), his love for the subject and his passion to help his students grow and learn were witnessed by those who sat around the Harkness Table.

In 1997, Kevin and his family moved into Goodwin House. Long time Goodwin House Head Ned Bean welcomed them to the Goodwin family and Kevin began his long journey as a member of the boarding community. Moving into a dorm did not seem like a daunting task for Kevin. Since he was a successful football coach, how difficult could it be to lead students and motivate them to make smart choices? But he soon learned it wasn’t going to be as easy as he expected.

During his first night of duty he met a charming student, who, like Kevin, was a new member of the dorm. He wanted to sign out to Burger King with a day student. This seemed reasonable, so Kevin signed the card and off they went. To make a long story short, after many hours went by without the student returning back to the dorm, the student had failed to mention that he was signing out to a Burger King in California. This incident taught Kevin to question all details whenever a student is filling out their blue card. During his time in the boarding community, Kevin performed dorm duty in six other dorms including a long career in Hallowell House.

And despite the unfortunate Burger King incident, he became a tremendous mentor, leader, and role model in each dorm that he was connected to.
Although his impact in the boarding community was tremendous, it has been his role as the head football coach that has shaped his legacy the most. Former players, coaches, colleagues and parents, will always remember the many football victories during his time with us, 242 to be exact, with a winning percentage of 70 percent. But it is likely that what will be most remembered is Coach Mac’s passion, determination, motivational speeches and the overall positive energy that he displayed each day on and off the field.

One of Kevin’s greatest strengths was building positive and caring relationships with everyone.

Many of his former players have shared stories about Kevin’s care, loyalty and support. He is known for creating an environment that builds confidence within his players, as well as humility; celebrating their successes with positivity, and helping them to learn and grow when mistakes were made. Drew Jacobs, a co-captain on the 2013 New England Championship Team, and now an assistant coach for the Harvard football program, called Coach Mac an “authentic leader.” He has shared that Coach Mac looks to “build strong relationships by opening himself up while seeking to create genuine connections with others.”

Mac’s unmatched ability to build and sustain such strong relationships is also evident in his coaching staff as well, several of whom are former players, such as Mike Mason. Mike played for Kevin nearly 40 years ago and has been by his side as an assistant coach for the past 27 seasons. Mike will be taking over as head football coach next fall and I know Kevin couldn’t be happier to see Mike continue to lead the Milton football program into the next generation.

In 2013, Kevin was inducted into the Massachusetts Football Coaches Hall of Fame and in 2023, he will also be inducted into the New England Prep School Athletic Hall of Fame. Both are tremendous and well-deserved honors, with his overall winning record placing him in the top 10 winningest coaches in the state of Massachusetts. Many believe that if Kevin had stayed at Archies for his entire career, where they typically have more games per season than Milton, he would have risen to the very top of that list. Although that would have been a tremendous accomplishment for Mac, we are all so glad that he chose to come to Milton.

Recently I was at a strength and conditioning seminar, and the speaker used the following metaphor: “always check to see if your buckets are full” when he spoke about designing training programs. The buckets represent important components such as speed, strength, power, conditioning, etc. If only a few buckets are full, you are not meeting the entire needs of your athletes.

I feel this same metaphor can be used for all coaches, with buckets representing many important elements that Coach Mac consistently demonstrates: the ability to lead, respect for others, compassion, loyalty, knowledge of the game, energy, devotion, care, and so much more. Looking back on Coach Mac’s career, one can say, without a doubt, that not only were his water bottles always full, but more importantly, all of his coaching buckets were filled to the top. In fact, they were overflowing.

Thank you Coach Mac for everything you have done for the Milton community and we wish you and your family wonderful days and years ahead in your retirement. And please know from our “toes through our souls,” we will always have PRIDE because of you!

Steven C. Darling
Head Strength and Conditioning Coach

The Community Issue

What do we owe to one another, our communities, and the world? In this issue, we take a look at what “community” means to Milton and the ways in which the school goes beyond the jargon to create genuine, mutually beneficial, lasting connections.