The Island is reeling after the passing of Oak Bluffs icon Dennis daRosa at age 71, whose love for his town had him involved in every facet of the community.
At age 12, daRosa was busy setting type and running the printing press for his father, who started daRosa’s in 1935 on Circuit Avenue. DaRosa joined his father’s company full-time in 1971, and in 1978, daRosa’s became one of the first businesses on the Island to use computers. They paid almost $80,000 for the first computer, which they needed because they could no longer manually handle billing. To offset the cost, they began offering the computer system to other Island businesses, to help with their accounting and payroll.
And with that, daRosa’s began to establish itself as the premier store to purchase hardware, office supplies, and technology of the highest caliber.
But the lifeblood of the business is the family that owns it, and daRosa knew that showing his customers how much he cared was the most important thing. Apart from being a businessman and philanthropist, daRosa was a fixture of life in Oak Bluffs, and was heavily involved with all aspects of the town. DaRosa was the head planner for Tivoli Day, a celebration of all the hard work during the summer, and a welcoming of fall.
While daRosa was the Oak Bluffs Association board president, he spent time with Christine Todd, who was the executive director of the association. Todd told The Times how much daRosa loved the Island, and how his extreme affinity for Oak Bluffs encouraged him to constantly try and make the town the best it could be. “He never gave up; he didn’t let things hold him back, and really kept his eye on the future,” Todd said.
Todd said she would visit daRosa frequently in his store to receive guidance, have a laugh, or hear words of kindness during tough times. “I wore a tread in that carpet walking into that store every day. He was always there to encourage me and lend a sympathetic ear,” Todd said. “He will be greatly missed by all, and will be remembered as a light of positivity and a major part of our community.”
Brian Packish said daRosa’s passing has left a void in Oak Bluffs and on-Island, as his role as a community leader was so strong. “I knew [daRosa] for a really long time, ever since I was little,” Packish said. “I grew up in Oak Bluffs, and that’s where you always went to get school supplies, over at daRosa’s. That’s where everything happened.”
In all the years of knowing him, Packish said, daRosa always stood for what makes the Island great, and helped forge a tight-knit community in Oak Bluffs. “He was definitely a pillar in our community. Just an all-around great guy who was really passionate about everything he did,” Packish said.
Bob Johnston, who worked with daRosa on the Martha’s Vineyard Futureworks organization, said, “The Vineyard lost some of its aura with the passing of Dennis daRosa.”
Johnston said daRosa was a close friend of his for over 20 years, and exuded the spirit of the Island in everything he touched. “It was Dennis’ curiosity and wonder about what an infusion of collaborative innovation might mean for the Vineyard and Vineyard community,” Johnston said. “This inspired a series of grassroots meetings in 2018 that gave birth to Vineyard Futureworks. A year ago at the new M.V. Museum, this organization, with Dennis’ leadership, hosted Making Tomorrow’s History Together, a Vineyard leadership forum envisioning a preferred future for the Island and Island community out 150 years,” Johnston said. “Who else on the Island could have brought leaders from our six towns together in this way?”
Attorney Ron Rappaport said daRosa and he were “best buddies” since they were 3 years old. They were elementary school classmates, and Little League teammates. “When we were growing up, there were three Little League teams: the Oak Bluffs Red Sox, the Tisbury Tigers, and the Edgartown Braves. And, as we remember it, Oak Bluffs was always the champion,” Rappaport said.
Rappaport said daRosa was always “the same wonderful person throughout his life — upbeat, mischievous, loyal, fun, and kind.”
“His family gave him his greatest joy. He was a wonderful son, husband, father, grandfather, sibling, uncle, in-law — just an all-around great person,” Rappaport said. “He would brighten your day with his presence. I will forever miss him.”
Ron Borges,now a Boston sportswriter, said he was best friends with daRosa since the two were 12 years old. They formed a strong bond while playing Little League baseball on rival teams.
“I didn’t talk much to Dennis, since he was the best pitcher in the league, and regularly sent me dragging my bat back to the bench after another futile attempt to get a hit,” Borges said. “I did occasionally manage to get on base, however, and once in a tight game came barreling toward home plate after a pass ball. Dennis was covering the plate, and we collided hard enough that the ball, and both of us, went flying in a pile of dust.”
As both boys lay on the ground, they could hear two women in the stands hollering at each other. “Dennis looked over and said, ‘Is your mother as crazy as mine?’ I affirmed that she was. We’ve been friends ever since,” Borges said.
In high school, daRosa was the quarterback, and Borges was his center. “There’s a lot of trust right there, at least on my end,” Borges said.
Borges called daRosa “the most positive-thinking person you could ever meet,” and said that
one summer, he came up with an idea to promote a concert on the Vineyard featuring Tom Rush, who was a hot artist in the folk world at the time.
“He ground the numbers, rented the Tabernacle, and had it all figured out, until Rush demanded to do two shows, not one, on the same night. I suggested even in the summer this seemed a bit much. Dennis said it would be great,” Borges said. “Dennis lost some bucks at a time when neither of us had any. I was distraught and more than a little peeved. Dennis just laughed with that snort he sometimes had, and told me, ‘It was a good plan. It just didn’t work out.’ Unconvinced, I said, ‘If they said that at Normandy, we’d be speaking German today.’ What did he say back? ‘Nein!’ Cracked us both up. That was Dennis.”
Borges said when daRosa got bad news a year ago from doctors at Massachusetts General that they’d found a cancerous brain tumor that was a serious problem, he was in the middle of eating breakfast. “He listened, knew it wasn’t good, and after a few seconds looked around and said to his family, ‘Can someone pass the jelly?’ That was the kid I barreled into at the age of 12, and am proud to say remained my friend for nearly 60 years: the unflappable Dennis daRosa.”
Allen Look said daRosa has been a dear friend, and his physical departure “leaves a deep sadness, yet a sadness mitigated by the great joy and gratitude I feel for having him and the entirety of his family as such an integral part of my life for these many years. The D-man is the truest of friends — a man of flawless integrity, unfailing good humor, and an inspiring, intelligent empathy for all humanity. I miss him as a brother, and look forward to our paths crossing again downstream. It’ll be a lovely day.”
Attorney Jim Reynolds said daRosa was his first friend on Martha’s Vineyard, and his warm and welcoming nature was unwavering throughout his life. “He remained as true a friend as I have ever had in my life, always available in good times and bad,” Reynolds said. “He had a positive take on whatever and whoever crossed his path. It was always such a simple pleasure to come into and share his company, even while he suffered with his illness.”
Reynolds said he will forever remember the warmth of daRosa’s friendship, and the devotion he had for his family.
Jim Spiro said he met daRosa 65 years ago, and they got to know each other through attending Grace Church, and through Island sports. Even when the two went off to college, they still saw each other regularly. “We were in each other’s weddings. Our relationship endured my leaving the Island for a career path and Denny returning to the Vineyard to the family business,” Spiro said. “At a distance, we had our children to raise and our lives to lead, and we still continued to be the closest of friends.”
Spiro said he will miss daRosa, but feels fortunate to have so many precious memories of their time together.
Friend Joan Rice said, “Dennis was always someone who could make you feel better. He always had a compliment, a wonderful laugh, and a ‘How are you?’ with genuine care and interest. He was always ready to plan dinner and spend time with friends. If he made a commitment, it was solid, always dependable. He loved his life.”
