Harold (Harry) Edward Daly Jr., 89

Harold (“Harry”) Edward Daly, Jr., 89, husband, father, beloved “Fred” to his grandchildren, lifelong Marbleheader and Shipyard legend, peacefully passed away on July 31, 2026, surrounded by loving family. Harry was born at the Mary A. Alley hospital in Marblehead on October 19, 1936, son of Margaret (Cunningham) Daly and Harold E. Daly, Sr. He spent his first years at Allerton Place and then 21 Commercial St. along with his parents and beloved sisters Patsy and Reba. He and his friends, proud members of the “Wharf Rats” gang, roamed the town causing all manner of mischief that would later become memorialized in stories he told year after year to friends and family. Harry was an altar boy at the Star of the Sea church and was a Boy Scout in Dan Riorden’s Troop 32 receiving the Ad Altare Dei Medal, (a medal given to selected Catholic Boy Scouts) from Archbishop Richard J. Cushing in Boston. When Harry was in the ninth grade, he and Eric Nyberg, Jr. were credited with saving the life of Charles Gerlach, 69, who was drowning off Commercial Street Pier. They jumped in the water, retrieved Gerlach, and Harry administered CPR he learned in Boy Scouts until firemen arrived.

Harry played football for Marblehead High School and graduated from MHS in 1954. He attended Massachusetts College of Art (Class of 1958) and graduated with a Bachelor of Fine Arts. It was there he met the love of his life, Elaine Caliri. They were married for over 66 years and together raised four children, Gregg, Glenn, Dianna, and Harold (“Ned”) Edward Daly, III. While raising his family, Harry built a successful career in advertising. He landed his first job at Scott Advertising after being hired by an ad executive whose lawn he had mowed. This put him on a path that ultimately led to Hill, Holliday, Connors and Cosmopulos, where he served as Senior Vice President. In 1982, he established his own advertising agency, Cosmopulos, Crowley & Daly where he served as CEO, President and Chairman. He was a member of the Advertising Club of Greater Boston, the New England Broadcasting Association (director 1976), the USO of New England (director) and a guest lecturer at Simmons College, Bentley College, Salem State College, Harvard Business School, Boston University, and Northeastern University.

Harry served his town and country. He was a proud member of the Finance Committee of Marblehead, an active member of Ocean Park Civic League, and an active member of the Marblehead Jaycees (Junior Chamber of Congress) where he spent many Christmas seasons selling trees to benefit various charitable initiatives. Harry served his country as a member of the Naval Reserves.

At his core Harry was an outdoorsman and up for anything that took him outside, particularly to the mountains or to the sea. He could be found on the weekends in the trees of Marblehead working with former Marblehead Tree Warden Dick Farrar. He was an avid mountain climber who climbed most of the mountains in the New Hampshire White Mountain Presidential Range. Every year, he would convince family, neighbors and friends to travel up to the Chimney Pond campground in Baxter State Park in Northern Maine. There, he would lead climbs up Mt. Khatadin with an army of kids in tow, and at night, join his friend Eric Nyberg at the campfire in reciting “The Cremation of Sam McGee” and other poems by Robert Service. An avid skier, he had many skiing adventures at mountains throughout New England, Durango CO and the European Alps. He was a member of the Stonehutters and the Boggestow Ski Club where he led many a musical evening after long days on the slopes. Harry loved boating and was a member of the Boston Yacht Club for many years. He raced on Dick Welch’s Rhodes 19 “The Real Gusto” and Charlie Quigley Sr.’s Etchells 22 “Chancy Too.” He sailed throughout New England, the Virgin Islands and the Caribbean and would often reminisce about a 1979 family sailing trip to the Virgin Islands where, on the front edge of Hurricane David, they recorded the fastest time sailing from Virgin Gorda to St. Thomas, bringing the family to safely ride the storm out in a sand bagged beach house. When he wasn’t sailing, you’d find him with his grandchildren on his motorboat “Ripple”, named after his favorite Grateful Dead song. A consummate musician, he learned to play ukulele from his mother and then learned guitar. He was a member of the band “The Tumbleweeds” playing music by Hank Williams, Johnny Cash and other country artists of the 50s and 60s. Throughout his life, the Daly living room was filled with family, friends and music. With Harry on the guitar and Elaine on the washboard, all joined in with guitars, banjos, ukuleles, washtub bass and any other contraption that would make noise, singing along to country and western music, George M. Cohan medleys, classic folk tunes from the 60s and 70s, and Irish music.

Later in his life, Harry lived for golf and Starbucks. A member of the Galant Golf Players, he was known to play 36 holes in one day and for playing in any weather, once insisting on finishing a round in a raging storm while visiting Howth, Ireland. For many years he enjoyed going to Starbucks every Monday through Saturday morning to meet with “the guys” to opine on a multitude of topics over coffee and, in Harry’s case, a chocolate chip cookie. Wherever Harry went in his life and work, he connected with people, was remembered for his great sense of humor, and had a way of bringing people together. He will be greatly missed by his family and his friends.

He is survived by his loving wife Elaine Caliri Daly, his children Gregg and wife Kristen Daly, his son Glenn and wife Carol Maselli Daly, his daughter Dianna and husband Tony Blackman, his son Harold “Ned” E Daly III and wife Kristin Hoff and his seven grandchildren- Christopher Daly, Alex Vazquez and husband Carlos Vazquez, Danielle Daly, Elena Daly, Cara Blackman, Ryann Gonzales and husband Dylan Gonzales, and Ian Daly. Family and friends are warmly invited to attend a celebration of Harry’s life on August 30, 2026 from 1 p.m. -4 p.m. at the Hawthorne Hotel, 18 Washington Square West, Salem, MA to share memories, music and friendship. 

Donations in Harry’s memory may be made to the Marblehead Museum, Kaplan Family Hospice House or other charity of your choice. For more information and online guestbook, please call Murphy Funeral Home at 978-744-0497 or visit www.MurphyFuneralHome.com.