It is with deep sadness that we announce the sudden passing of Jonathan Charles Cunningham, who died peacefully in his sleep on August 12, 2025 in Chatham, MA, at the age of 65.

Jon was born on February 10, 1960 in Boston, MA. He grew up in Lincoln, MA with his parents, Robert and Margaret. Jon graduated from Lincoln Sudbury High School and earned his Bachelor of Business Administration from Babson College. A standout lacrosse player nicknamed "Bama," Jon was proud to be part of Lincoln Sudbury's 1978 state championship team and cherished the lifelong friendships he built with his teammates and coaches.

After graduation, Jon joined his father in the family wholesale hardware business, C.A. Cunningham Company. He greatly admired his father's work ethic and compassion, which he sought to emulate when he assumed the role of company president. Later, Jon became a sales representative, enjoying the relationships he built in the industry.

Jon met his wife, Kathy Dempsey, on a blind date. They married in 1990 and raised three daughters in Wayland, MA. Jon never hesitated to offer advice to his daughters, host a gathering of their friends, and was a loud cheerleader at all games. After the kids moved out, Jon and Kathy enjoyed many wonderful trips together. They also loved playing cards and backgammon, sharing both laughter and friendly competition while listening to their favorite songs. Jon brought his quick wit and sense of humor to his role as a grandfather, always finding a way to add in some extra fun.

Jon loved spending summers in Chatham, MA, where he developed a lifelong love for the water. His happiest days were those filled with sun and salt air, gathered around the grill with family and friends. He was also a member of the Chatham Beach and Tennis Club, a place that held countless treasured memories, including his daughter Susan's wedding.

Jon had a rare gift for making people feel seen and valued, and his easy laugh and thoughtful nature left an impression wherever he went. He will be missed greatly.

Jon is survived by his wife of 34 years, Kathryn Cunningham, their three daughters Susan (Shawn) Kelly of Concord, MA, Michelle Cunningham (Casey O'Brien) of New York, NY, and Amy (Jack) Maguire of Washington, D.C., and his two grandsons, Connor and Griffin Kelly. He was predeceased by his parents, Robert and Margaret Cunningham, and his in-laws Jack and Marie Dempsey. He also leaves behind many other extended family members in the Cunningham and Dempsey families.

Visiting hours will be held on Thursday, August 21 from 4:00 to 7:00pm at Dee Funeral Home, 27 Bedford Street, Concord, MA. A graveside service will be held on Friday, August 22 at 11am in Lincoln Cemetery, 44 Lexington Road, Lincoln, MA, with a reception to follow. Friends and family are welcome to attend and celebrate Jon's life.

Over the past six years Jon relentlessly supported his wife, Kathy, in her ongoing battle against pancreatic cancer. In lieu of flowers, please consider donating to Dana Farber Cancer Institute. To give by mail, send a check payable to Dana-Farber Cancer Institute and remit to: Dana-Farber Cancer Institute and the Jimmy Fund, 10 Brookline Place West, 6th Floor, Brookline, MA 02445. Please note your gift is intended for Dr. Ben Schlechter's research (Kathy's doctor) and made in memory of Jon Cunningham on the memo line. Gifts can also be made online: https://danafarber.jimmyfund.org/goto/benschlechter .

Arrangements are entrusted to Dee Funeral Home & Cremation Service of Concord.