Obituary published on Legacy.com by Casper Funeral & Cremation Services on Mar. 16, 2026.
Dan McCole, a beloved South Boston artist, newspaperman, and larger-than-life personality widely known as “Southie’s oldest teenager,” passed away peacefully on March 12, 2026, at the age of 96. Over the course of a long and colorful life, he was many things: a newspaperman, painter, writer, singer, teacher, mentor, uncle, friend, grandfather, great-grandfather, and father; but above all, he was a man who embraced life with creativity, humor, and an open heart.
Born in 1929 in South Boston to Philip and Margaret (McGonagle) McCole, who had immigrated from County Donegal, Ireland, a few years earlier with three of his older siblings, Dan grew up deeply proud of his Irish heritage and his South Boston roots.
At just sixteen years old, shortly after the end of World War II, he enlisted in the United States Army and spent much of his service stationed in Panama. After returning home, he attended the Vesper George School of Art, where he first learned to channel his creative instincts into painting. Though a newspaper career and raising a family would put his artistic ambitions on hold for several decades, the seeds of the artist he would later become were planted there.
Dan joined the Boston Herald Traveler as a part-time editorial artist and gradually built a full career in the newspaper business. His entrepreneurial spirit soon led him to found the Weymouth News, a weekly newspaper, where he filled nearly every role imaginable: publisher, editor, reporter, photographer, ad salesman, circulation manager, and bookkeeper.
After ten years, he sold the Weymouth News but remained involved with several local publications before returning to the Boston Herald, where he served as production news editor, late news deskman, and occasional feature writer. During his newspaper career, he received a first-place award for Best Column from the New England Press Association.
In November of 2000, he experienced a moment every newspaperman dreams about. The Boston Herald had just finalized its front page declaring Al Gore the winner of the presidential election when events suddenly became uncertain. Dan was the one who got to run into the pressroom and shout the legendary words: “Stop the presses!”
In the early 1990s, as family responsibilities eased, Dan returned to the artistic passion he had set aside decades earlier. He enrolled in a watercolor refresher course as a way of forcing himself back into painting and soon began entering his work in local art shows. When one of his paintings won a ribbon at the South Shore Art Show, the encouragement convinced him to devote more time to painting.
His art quickly gained a devoted following. A media story once noted that nearly every home in South Boston seemed to have a Dan McCole painting on its wall. His work appeared on a book cover, in movie sets, and even on an ornament for the White House Christmas tree. His painting of Ted Williams once became part of a friendly baseball wager between the mayors of Boston and another city whose team Red Sox fans prefer not to mention; the painting ended up hanging in New York’s City Hall for a year.
His artistic contributions were widely recognized in exhibitions and by civic leaders. The City of Boston proclaimed May 11, 2011, as Dan McCole Day in recognition of his impact on the community and the arts. A South Boston restaurant even created a signature drink in his honor (a wee bit stronger than a Shirley Temple/Bobby Orr). He was also particularly proud to be included in a coffee-table book celebrating Boston’s Irish Americans, and was delighted to see his page appear ahead of Conan O’Brien, the Dropkick Murphys, Tom Brady, and several members of the Kennedy family.
Beyond his accomplishments as a newspaperman and artist, what people remember most about Dan McCole was the genuine way he lived. He had a magnetic personality: engaging, charismatic, and full of laughter. Music, conversation, and storytelling seemed to follow him wherever he went. A proud son of South Boston with a deep Irish spirit, he had an enormous circle of friends and acquaintances who were drawn to his warmth and authenticity.
Even at 95, as a huge crowd gathered in South Boston to celebrate his birthday, he happily took the microphone and entertained the gathering by singing Irish favorites and standards from the American Songbook, an image that perfectly captured the joyful, larger-than-life presence that so many people knew and loved.
Family was always at the center of his world. Though he maintained a long career, his children remember that he somehow managed to be present in their lives. As his family grew, he became a beloved patriarch who delighted in bringing generations of friends and family together. To his grandchildren, he was affectionately known as “Cousin Papa,” a nickname earned one summer day when he spent hours jumping off a pool diving board and splashing around with the kids until they decided he behaved more like one of the cousins than a grandfather. Whether cracking jokes, setting up elaborate pranks, or filling a room with song and laughter, he never lost his playful spirit.
Behind the joy and humor was also a generous mentor who believed deeply in the power of creativity. Dan encouraged everyone around him to find and express their artistic voice. He mentored young artists, supported teens through art and service projects, and reminded us all that life itself becomes the raw material for art. His own life reflected that philosophy: fearless, curious, and open to the world. To many he was an artist, to others a teacher or mentor, but to all who knew him, he was a kind and genuine man whose warmth, creativity, and boundless charisma made him unforgettable.
Dan is survived by his four children: Carole Ann Wool (Jon) of Western Springs, IL; Christina Johnson (Rick) of Hollis, ME; Catherine McMahon (the late Dan) of Weymouth, MA; and Dan McCole (Jill) of Okemos, MI. He is also survived by longtime friend Nancy Powderly, seven grandchildren, four great-grandchildren, and many cousins, nieces, and nephews.
In addition to his wife, Carole, Dan was predeceased by his brothers John J., Thomas P., Philip J., Michael Leo, and Robert C., McCole, and by his sisters Mary Ann Bergin and Margaret “Peg” Reardon.
Visiting hours will be held at Casper Funeral Home, 187 Dorchester Avenue, South Boston, on Wednesday, March 18 from 4:00 p.m. to 7:00 p.m., and Thursday, March 19 from 11:00 a.m. to 12:00 p.m. A Funeral Mass will be celebrated at St. Brigid’s Church, 845 East Broadway, South Boston, on Thursday, March 19 at 12:30 p.m., followed by burial at Cedar Grove Cemetery.
Due to the Lenten season, the church is unable to display flowers. In lieu of flowers, donations may be made to St. Brigid’s Parish.
