Joseph Martin Phelan died on June 22, 2025, at Christopher House in Worcester. He is survived by his wife, Lynn (O’Connor Barrette).
Joe was born in Flushing, NY, on November 11, 1949, the first of seven children brought into this world by James and Margaret O’Connell Phelan. He moved with his parents and three younger siblings to Kings Park, NY in June 1955 and then with the whole clan to Clark, NJ, in 1964. His siblings included his youngest brother Gerard, who predeceased Joe. Gerard and Joe were true friends, and although separated by miles, spoke on the phone daily. Joe leaves behind 5 siblings, James Phelan (Betty), Mary Ellen Phelan (John), Betsy Phelan (Paul), Terry Bogsted (Roger), and Peggy Phelan. He also leaves children, Luke and Rachael Phelan.
Joe leaves many lifelong friends: Bob Kissane (Jeanne), who he met his first week at Holy Cross, as well as Tommie George (Linda), Danny Cotton (Gerrie) and Roger Challen (Karen), friends met from the Crompton Park basketball league. Joe treasured these friendships.
As the oldest, Joe was the family trailblazer in his second-generation Irish Catholic family: the first to go to college, the first to go to Europe — the Role Model. He graduated from Union Catholic High School in 1967 and attended the College of the Holy Cross, where he majored in history and played on the basketball team. He loved basketball and worked tirelessly to improve his skills. He turned down a basketball scholarship at Stonehill College in favor of attending what he regarded as the more academically challenging school, Holy Cross, where he “walked on” to varsity and eventually became a reliable sixth man. After graduating in 1971, Joe played professional basketball for two years in Essen, Germany. He spoke no German when he landed in Essen but soon became fluent.
Joe returned to Worcester in 1973, where he began teaching at North High School, combining teaching with coaching basketball while pursuing his Ed.D at the University of Connecticut. He had a long career in education, creating and directing the Alternative Education program at Auburn High School. However, Joe would be first to tell you, “Work is overrated.” He embraced life with passion and cherished time outdoors, running in a park or sitting on the beach. He was an avid reader, often devouring several books a week. He remained a committed athlete and fan, following the successes of local football, baseball and basketball teams, as well as track and field. Joe loved Patriots Day and the Boston Marathon. He enjoyed traveling. A trip of special significance was with Lynn to Europe in 2013. The trip included traveling back to Essen to share where he lived and played ball.
Joe was a collector, and drinker, of fine wines, enjoying Friday night tastings hosted by Jim at O’Haras. He loved attending the Kevin and Erla hosted 4th of July parties. Post-stroke, Joe really enjoyed sitting at a bar having dinner with Lynn, and made many new friends. His favorite spots and people were: The Mill, Uxlocale (especially Chad), and Quaker Tavern in Uxbridge. Until very recently, Lynn and Joe continued to enjoy Friday night dates, and enjoyed the special attention provided to them by Quaker Tavern proprietors, Mike and Nancy Bogan, bartender Felicia, and buddy Darren.
Joe’s combined natural charisma with genuine care for others made him not only an inspirational teacher but a beloved husband, stepfather, brother, and friend. His greatest gift was his ability to connect with other people. He had a quick wit that was often on display in sardonic, even withering takes on everything from politics to education to Boston sports teams. But his more-cynical-than-thou exterior masked a more-loving-than-anyone interior. This combination worked wonders for countless Auburn students who went through the Alternative program under his direction. The combination also made him wonderful company, someone who exudes cool, someone you could laugh with and know that the laughter was deepening your mutual connection. Joe’s love for Lynn and her love for him were boundless; all who knew them found their love awe-inspiring.
Joe’s life changed significantly after suffering his first major stroke in 2016. He experienced serious aphasia, making language difficult. He had deep respect and affection for those who hung in with him as he struggled with language expression. He always appreciated the kindness and dignity shown by his stepchildren, Michaela Hayston and Kevin (Buzz) Barrette and Buzz's wife Jen, as well as Lynn's siblings and spouses, Cynthia and Lou Ciavarra, Caryn O'Connor and Mike Holden, Matt and Tracy O'Connor, and Lynn’s former husband and spouse, Kevin Barrette and Belinda Melanson. Joe’s deep bonds of friendship were evident in the outpouring of love and support after his strokes. So many people helped with Joe's care. Friends Karyn, Annette, Jen O. and Brian, CNA Sarah-Beautiful, Lynn’s family members and Joe’s friends, especially Danny, always jumped in to lend a hand. Joe formed new bonds with all who cared for him at Christopher House, especially Jeny, Nash, Nora, Jenna, Lynn, Isaac and Pius, whose care showed compassion far beyond a work commitment. His grandchildren, Addie and Bo Barrette, and Isla and Barrette Hayston always brought a smile to Joe’s face.
Joe will be remembered during a Celebration of Life on Sunday, July 20th at Cyprian Keyes, 284 E Temple St, Boylston, MA 01505 from 2:00p.m. until 5:00p.m. Joe, being Joe, would like people to dismiss thoughts of mourning clothes, and dress in anything festive. Lynn would love any “Joe inspired” choices. O’CONNOR BROTHERS FUNERAL HOME, 592 Park Avenue is assisting the family with arrangements. To leave a memory or message of condolence, please visit www.oconnorbrothers.com.