John Malachy Dooley of Wellfleet, a bagpipe player, avid fisherman, and former Provincetown High School guidance counselor, died of congestive heart failure on June 17, 2025 at the Liberty Commons long-term care facility in Chatham. He was 82.
“He was known for his big laugh, generous heart, and the unmistakable twinkle in his eye that made others feel like they had known him forever,” said Jack’s daughter Nora.
Jack was born on June 10, 1943 in New York City to James Dooley, an Irish immigrant who worked as a signal operator for the New York Transit Authority and as an ad runner for the Daily News, and Elizabeth, a homemaker. He grew up in the Bronx, where he played football at Mount Saint Michael Academy before transferring to Rice High School, which stoked an early interest in music.
He went on to earn a B.A. in history and political science from Iona University in New Rochelle, N.Y. — where he played the bagpipes and co-founded the Iona University Pipe Band, which still exists. Jack continued to play the bagpipes off and on for the rest of his life, including as president and pipe major of the Cape and Islands Police and Fire Emerald Society Pipes and Drums.
Jack met his future wife, Mary Ann Barrett, at an Iona-Hunter College mixer, and they married in 1967 — on his birthday, so he “would always remember the date,” Nora said he quipped.
He earned an M.S. in counseling and guidance in 1970 at Fordham University, then became a doctoral candidate at the UMass Amherst School of Education, where he pursued a degree in mental health and human systems design and administration.
Jack and Mary Ann left the Bronx and resettled several times — first in Tarrytown, N.Y., where both worked at the Institutes of Applied Human Dynamics; Jack became director of the pre-vocational and recreational program for neurodivergent and intellectually disabled youth.
Next, they lived in Western Massachusetts. In 1977, after falling in love with Cape Cod on a family vacation, the family moved to Eastham, where Jack coached Little League for a time.
Jack became a guidance counselor at Provincetown High School, where he stayed for 10 years — and, in perhaps his most popular role, coached the boys basketball teams and founded and directed the Provincetown-Truro Little League co-ed basketball program.
“We would go out to eat or shop in Provincetown and my dad was like this rock star,” said his daughter Jessica. “All these kids would be like, ‘Hey, Coach Dooley!’ It seemed like he was beloved.”
“He was known not just for his passion for the game,” added Nora, “but for the kindness and integrity he modeled with every practice and post-game chat.”
Jack left his guidance counselor job in the 1980s and became a real estate agent, first with Ireland’s Real Estate in Orleans and then for his own company, Seashore Realty, in Eastham.
“I think he wanted to just try different things,” said Jessica, who recalled him having summer stints landscaping, running a lawn-mowing business, and fishing and shellfishing on boats that he owned. “He was the embodiment of the jack of all trades and liked changing things up.”
Later, he joined the Orleans Police Dept. as a radio dispatcher and started his own Seashore Livery service, ferrying clients to and from the airport and doctor appointments.
Once their kids were grown and on their own, Jack and Mary Ann moved to South Wellfleet, where Jack juggled various volunteer jobs — for Meals on Wheels, for the Cape Cod National Seashore’s over-sand permit office and bike-trail patrol, and for the Wellfleet Adult Community Center, providing rides to seniors. Driving people with cancer to medical appointments was a calling for him, having learned the importance of it when Mary Ann went through breast cancer treatment in her 30s and again when the cancer returned in her 60s.
When she died of the disease in 2011, Jack’s heart “broke to pieces,” said Nora.
In his grief, he sought change, which included attending services at Grace Chapel in Wellfleet and joining a ukulele class taught by McNeely Myers in Orleans.
“He loved to sing and make joyful noise,” said McNeely. They became friends and eventually housemates when Jack told her he had room at his place and could use the company.
“We were buddies through the pandemic,” she said, adding that among Jack’s favorite songs were “Keep on the Sunny Side” and “Everyday” by Buddy Holly. “He was such a dear man and just so cheerful.”
Jack also purchased a classic Volkswagen Karmann Ghia convertible and drove it to visit his son in New Mexico, where he lived for two winters, joining ukulele jam sessions with the Las Cruces Ukes.
As a final passion project in 2015, Jack founded the Wellfleet PorchFest, part of a national network of music events in which musicians perform on porches for the local community — a fitting legacy for a musical man known for his generosity of spirit, said Jessica.
Jack is survived by his son, Christopher Dooley, and wife Kelly of Las Cruces, N.Mex.; daughter Nora Moreno and husband Allen of Los Angeles; daughter Jessica Rempel and husband Dave of Wellfleet; sister Betty Lind of Southold, N.Y.; sister Marian Dooley of Somers, N.Y.; sister Geri Conklin and husband Tom of Castleton on Hudson, N.Y. and their daughters, Kris Conklin of Chatham, N.Y. and Jen Russo of Phoenix, Ariz.; and four grandchildren.
There will be no funeral service, as was Jack’s wish, but those wanting to honor and remember him are encouraged to attend or otherwise support Wellfleet PorchFest.
