WHY I GIVE
Finding Extraordinary Opportunity MATT DEFEO ’82 GIVES BACK TO THE PLACE THAT LAUNCHED HIS FUTURE
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ast fall, when delivery trucks arrived at Cushing Academy’s facilities department, Brandon Monat and his crew found boxes upon boxes of brand-new Milwaukee Tools. “We don’t often receive gifts like that,” says Monat, Cushing’s director of facilities. The generous donation came from Matt DeFeo ’82, an alumnus who wanted to give back to the people who keep Cushing running behind the scenes. DeFeo and his company Milwaukee Tool’s thoughtful gift reflects the same attention to detail that marked his successful business career. He asked the facilities team for a wishlist to ensure maximum impact. DeFeo’s desire to give stems from his own transformative experience at Cushing — one that began when he left Martha’s Vineyard as a 14-yearold to attend the Academy. “My mom was a single parent with four kids. We didn’t have much,” he says. “Cushing made it financially feasible for me to attend, and it changed everything.” With the help of scholarships and summer jobs, DeFeo earned money for part of his tuition. “It was $8,200 back then. My family paid $2,000 a year, and I paid half of that. It was a lot, but it was worth every penny.”
At Cushing, DeFeo found more than a strong academic foundation — he found mentors who saw potential in him and gave him the tools to thrive. “Coach Wayne Sanborn ’99 (Hon.), P’02 was one of those people,” DeFeo says. “He was a mentor, a leader. I’d hang out in his office between classes. He helped me become someone who believed in myself.” Paul Dowling ’15 (Hon.), P’99, his wrestling coach, also left a mark. “He was tough, but he taught us discipline, grit, and how to never quit,” DeFeo recalls. “He drove us hard, and we won Cushing’s first-ever New England Class A Championship in wrestling.” DeFeo took fourth in New England that year, captained the lacrosse team, and served as class president. Cushing, he says, wasn’t just about athletics — it was about inclusion. “I participated in drama. I had leadership roles,” he emphasizes. “At a bigger public school, I never would have had those chances. At Cushing, there was a place for everyone.” After graduating, DeFeo attended Northeastern University, where he worked his way through school via the co-op program. Coming from Cushing, it was a culture shock. “I was used to
unbelievable teachers, and I could get help at any time,” DeFeo says. “What Cushing helped me with is having a study hall every night for four years from 8 to 10 pm. It prepared me to know that I had to study at night.” DeFeo then went on to a successful career. He spent the last 18 years of his career at Techtronic Industries, ultimately serving as group president and helping grow the company from $2.2 billion to over $14 billion before retiring in 2024. He credits Cushing with teaching him how to lead. “When I retired, I had 2,300 employees, and I always tried to create a family culture — just like Cushing had,” he says. “I treated everyone with respect, from entry-level hires to senior executives. That’s what I learned there. Cushing had an incredible culture.” Giving back is personal for DeFeo, who serves on the Alumni Council. “I check the box every year to direct my gift to scholarships, because someone did that for me. There are so many kids like I was — full of potential but without means. If we don’t open that door, we might never see what they can become.” His message to fellow alumni? “If Cushing shaped you — even a little — give back.”
WINTER 2026
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