James Richard Regan “Jim“ left this world peacefully at the age of 94 on June 18, 2026, following complications from hip surgery. He was surrounded by family in the days prior to his passing.

Jim was born on September 22, 1931, in Boston, Massachusetts, to James and Katherine Regan. He was a proud graduate of Boston Latin School, earned his bachelor’s degree from Boston College, and went on to receive a master’s degree from Dartmouth’s Tuck School of Business. He served as a corporal in the United States Army from 1952 to 1955, during which time he studied Russian at the Army Language School in California and was stationed in Japan.

Jim taught business classes at both Concord High School and Manchester High School in New Hampshire, serving some of that time as department chair, and then retiring in 1993. During the summer months, he worked a wide variety of jobs, from driving an ice cream truck to managing books for a motel, and he served for many years as the maître d’ at The Moors, a prominent Portuguese restaurant in Provincetown. Upon retirement, he moved to Provincetown, Massachusetts, and later to Fort Lauderdale and Boca Raton, Florida. More recently, Jim moved to Standish Village in Dorchester, Massachusetts, to be closer to family.

Jim was a stickler for propriety and a deeply social person. Those who met him often described him as “such a gentleman.” His eclectic circle of friends, wherever he lived, gave him the opportunity to share in a wealth and variety of experiences and travel, which he truly enjoyed. He often shared memories of traveling in Europe, sailing the Caribbean on a friend’s sailboat, crossing the country by train to tour the National Parks, and sailing aboard the Queen Mary II. He was especially fond of his annual trips to Tanglewood with his friend Harry, who shared Jim’s love of classical music. Jim also was able to collect many types of art during his travels, though works by local Provincetown artists had a special place in his heart.

Jim was predeceased by his sister, Alice R. Daly, and her husband, Paul D. Daly; and by his close cousins, John and Roger O’Donnell, and Mary (O’Donnell) O’Meara. He is survived by Alice and Paul’s eight children: Kathy Daly and Doreen Quintiliani of Shirley, Massachusetts; Paul D. Daly and Lila (George) Daly of Woodstock, Georgia; Susan and Jim Curley of Milton, Massachusetts; John Daly and Kathy (Lake) Daly of Milton, Massachusetts; Michael Daly of Milton, Massachusetts; James Daly and Sue (Tagliareni) Daly of Melrose, Massachusetts; Gerard Daly of Scarborough, Maine; and Liz and Flip Rosenberry of Amherst, Massachusetts. He is also survived by the many children of Roger, John, and Mary, as well as numerous great-nieces, great-nephews, grandnieces, and grandnephews.

A Mass of Christian Burial will be celebrated at Our Lady of the Visitation Parish, Saint Elizabeth Church, 350 Reedsdale Road, Milton, Monday June 29 at 10:00 AM. Family and friends invited. Burial will follow in St. Joseph’s Cemetery in West Roxbury, MA.

In lieu of flowers, donations may be made to Sisters of Charity of Saint Elizabeth, P.O. Box 476, Convent Station, NJ 07961 or to the Fine Arts Work Center, 24 Pearl Street Provincetown, MA 02657 https://fawc.org/.