James A. Cunningham

1943 - 2025

James A. Cunningham
01/20/1943 - 12/29/2025
James A. Cunningham, 82, of Wolcott, entered into the gates of heaven on Monday, December 29, 2025, at his home in Wolcott, surrounded by his loving family. He was the beloved husband of Maureen (Ward) Cunningham of over fifty-nine years.
James was born on January 20, 1943, in Malone, New York, to the late Allen E. and Alice (Stark) Cunningham. He grew up on the family farm and graduated from Franklin Academy in 1960, where he was a member of the football and track teams. During his junior year, he earned Football All-American honors.
He went on to attend the State University of New York at Brockport, where he met his wife, Maureen. A 1964 graduate, James earned a Bachelor of Science degree in Health and Physical Education and was an active member of the football and track teams. In 1962, he was one of the founders of the Brockport Lacrosse Club. He later earned his Master of Science degree in Health and Physical Education from SUNY Brockport in 1968.
James began his teaching and coaching career in 1964 at Cardinal Mooney High School in Rochester, New York. There, he taught Physical Science, Biology, and Physical Education, served as assistant football coach (later junior varsity coach), and was head track coach. He also established the school's first-ever wrestling program.
In 1971, James moved to Wolcott, Connecticut, where he accepted the position of Athletic Director at Holy Cross High School. In addition to his director duties, he taught Physical Education and served as assistant football and track coach. Continuing his legacy of program building, he established Holy Cross High School's first wrestling program.
In 1989, James retired as wrestling coach but continued coaching field events in both winter and spring track. After 40 years in education, he retired from Holy Cross High School in 2004, yet remained active by continuing to coach field events in spring track. From 2005 to 2014, he served as an assistant wrestling coach at Xavier High School in Middletown, Connecticut.
Throughout his career, James received numerous honors, including CIAC Wrestling Coach of the Year, CAS Athletic Director of the Year, and the Olympian Award. In 2010, he was inducted into the National Wrestling Hall of Fame. He was also a member of the Holy Cross Hall of Honor.
During retirement, Jim and Maureen greatly enjoyed traveling to their grandchildren's athletic events, visiting friends, making yearly trips to Florida, and traveling throughout the United States and around the world. River cruises were a particular favorite.
Jim was also an avid gun and knife collector and a dedicated woodworker. He especially enjoyed spending time in his basement "shop," where he took pride in making and repairing anything and everything.
James was a member of the Bristol Fish and Game Club and the National Rifle Association.
His lifelong dedication to education, athletics, craftsmanship, and family left a lasting impact on the many lives he touched.
Besides his beloved wife Maureen, Jim leaves behind to cherish his memory his two sons, Michael Cunningham and his wife Kira of East Berlin, CT, and Thomas Cunningham and his wife Janeen of Poughquag, NY. He also leaves behind his four grandchildren, Tyler Cunningham and his wife Meghan, Colin Cunningham and his wife Sarah, Courtney Cunningham, Shannon Cunningham, his great-grandson, John "Jack" Cunningham, as well as many nieces, nephews, great nieces, and great nephews. He was predeceased by his siblings, Robert Cunningham, William Cunningham, and Bertha Gallagher.
Arrangements: A funeral service will be held on Saturday, January 3, 2026, at 10:00 a.m. at Chase Parkway Memorial, the Albini Family Funeral Home, 430 Chase Parkway, Waterbury. Burial will follow at Edgewood Cemetery in Wolcott. Calling hours for Jim will be held Friday evening from 4:00 – 7:00 p.m. at Chase Parkway Memorial.
In lieu of flowers, memorial contributions can be made in Jim's memory to:
Holy Cross High School's:
James Cunningham Athletic Complex Fund
Or
James Cunningham Scholarship Fund
587 Oronoke Road
Waterbury, CT 06708
For more info or to send e-condolences visit: www.chaseparkwaymemorial.com