Greg Michael Flaherty

Woolwich - Greg Michael Flaherty, 74, passed away peacefully on December 12, 2025, after a 5 month battle with cancer.

A lifelong Mainer, Greg grew up in Westbrook, graduating with the WHS class of '69. Throughout his life, involvement in organized sports was a constant, playing football and baseball in high school. This was followed by a post-grad year at Bridgton Academy where he was a member of their first and only undefeated football season, for which he was inducted into the BA Sports Hall of Fame in 2010.

Greg went on to attend the University of Maine at Orono where, as a freshman, he played football, joined Sigma Chi Fraternity and met the love of his life, Jeannie. They married in 1973, settling in Portland. During those early years Greg continued his studies at UMPG (now USM), working a couple of summers as a stern man on his friend, Lyman's, lobster boat. He also played competitive touch football on the Hank's Cookies and Forest Gardens teams. Greg always said that those years were "the best of times with the best of friends". Football and his "frat brothers" provided him with a lifetime of memories and friendships that he cherished always. When he finally hung up his cleats, he became a longtime member of the Southern Maine Board of Football Officials, serving as a Board President at both the state and local level, pouring countless hours into the sport he loved. He shared his passion with his daughters, working chains with Jill at the annual Turkey Day games and Carla at the State Championship games.

In 1984, Greg & Jeannie built their dream home in Gorham where for 30 years the Fort Hill Farm neighborhood provided the BEST and most treasured community in which to raise their family. Moving to Woolwich in the pandemic, Greg (Cap'n McGregor) bought his first boat, which he and Jeannie loved to share with family & friends, while enjoying the changing seasons and endless sunsets overlooking the Kennebec River.

Greg had a long and respected career at Unum, retiring as Director of Global and Computer Risk Compliance in 2015. On retirement he was recognized for his "knowledge, experience, business savvy, executive presence, quick wit, and sense of humor".

Foremost, family was at the center of Greg's world. He was a devoted, loving husband and the best "girl dad" ever. His heart expanded with each new member welcomed into the family, from "West" Virginia to Ireland.

Greg was predeceased by his beloved daughter, Robin Flaherty. He is survived by his wife of 52 years, Jeannie (Wilson); his daughters Jill (partner Ken Lynam), Carla Flaherty (husband Neil Miller); and his cherished granddaughter, Ember, who brought him immense joy.

A Celebration of Life will be held on Saturday, December 20th, from 2–4 PM at the Maine Irish Heritage Center. Family and friends are invited to gather, share memories, and honor Greg's remarkable life. As a tribute to Greg's love of family ancestry research, donations can be made to the Maine Irish Heritage Center, 34 Gray St, Portland, ME 04102