Eileen Cunningham, the heart and soul of St. Ann’s Color Guard of Neponset, Massachusetts, passed away on August 30, 2025, after a lifetime devoted to young people, color guard, and her beloved community of Dorchester. She was 72.
In 1965, Eileen walked into the Victory Road Armory for what was supposed to be her first—and perhaps only—St. Ann’s color guard practice. Instead, that day marked the beginning of a journey that spanned six decades. What started as a teenager’s unexpected rehearsal grew into a calling that shaped thousands of young lives and transformed St. Ann’s into one of the most successful and respected color guard organizations in the world.
Eileen taught the joy of color guard to generations of young people. She marched alongside her sisters, became captain, and turned her energy to teaching, mentoring, and leading. In 1992, she became Director of St. Ann’s, a role she held for 32 years, creating what many call a dynasty in winter guard.
Under her leadership, St. Ann’s earned 24 WGI finals appearances, including 12 medals (5 Gold, 6 Silver, 1 Bronze). The organization became a laboratory for innovation, introducing iconic tosses and routines that spread across the activity and remain staples to this day. In 1999, St. Ann’s World Guard became the first winter guard ever to perform two completely different programs from Act One in prelims and Act Two in finals. In 2002, St. Ann’s made history again by fielding two Independent World Class teams that advanced to WGI Finals.
Beyond accolades, Eileen’s greatest impact was personal, as evidenced by the outpouring of love on social media after her passing. Former students remember her as a mentor, a second mother, and a constant source of strength.
In 2014, Eileen was inducted into the Massachusetts Drum Corps and Music Educators Hall of Fame, and in 2019, she received one of the activity’s highest honors: induction into the WGI Hall of Fame.
But her proudest achievement was always her students. Generations of families performed and grew under her care. Once you joined St. Ann’s, you became part of what she called a “forever family.” As one student said, “Everyone knows Eileen, and everyone loves her with all their heart. If any of us becomes half the woman she is, the world will surely change.”
Eileen leaves behind not just her family, but the countless members of her St. Ann’s family—spanning decades, states, and even countries—who will forever carry her lessons of discipline, grace, and love.
She lived her life believing that the little things are the big things. And for all those who were lucky enough to learn from her, those little things will echo for generations.
Sleep well, Dollface.
Funeral Mass in St. Ann’s Church, 243 Neponset Ave., Dorchester on Friday, September 19, 2025 at 11:00 AM
Interment will be private
In lieu of flowers, please consider making a donation in her memory to St. Ann’s Colorguard
St. Ann’s Colorguard
c/o Marry Rutter
35 Majorie Road
Braintree, MA 02184
