James William Dempsey

James William “Jim” Dempsey, age 82, of Edgewood, Maryland, passed away peacefully on November 20, 2025, surrounded by the love of his family.

Born and raised in Middle River, Maryland, Jim was the son of the late James and Eva Dempsey (Abell), and brother to Edwin and Regina (Wilcox), who also preceded him in death. He was a proud graduate of Towson State College , where he earned his Bachelor’s degree in Education, and later completed his Master’s degree at Morgan State University.

Jim dedicated 38 years of his life to teaching mathematics at the middle school, high school, and community college levels. He was a gifted educator whose patience, wit, and ability to simplify complex ideas changed the lives of thousands of students.

A lifelong member of St. Stephen’s Catholic Parish, Jim lived his faith quietly and through his actions — with kindness, humility, and service.

Jim was also a deeply passionate supporter and builder of local soccer in Harford County. He helped establish recreational leagues, supported travel programs such as ROX Soccer, and was instrumental in developing the soccer program at St. Stephen’s School, passing the love of the game on to countless young players. He also volunteered at Harford Community College’s summer soccer camps, helping introduce the sport to new generations. His influence continues today through the families, coaches, and players he inspired — including his own sons and grandchildren who inherited his love for the game.

Beyond teaching and soccer, Jim was known for his sharp mind and love of strategy. He was an avid chess player and as a young man was a rated player with the American Chess Federation. He was active in local clubs, and cherished time spent reading, learning, and writing letters to the editor of the Baltimore Sun and debating ideas. His humor, stubborn Irish streak, and deep loyalty made him unforgettable to everyone who knew him.

Jim is survived by his loving wife of 57 years, Carolyn Dempsey (Cherry), and their five sons: James and wife Nancy, Michael and wife Jenny, Shawn and wife Kara, Patrick, and Timothy and wife Shannon. He was an exceptional grandfather to his ten grandchildren, whom he adored and supported in every way: Jeremiah, Jack, Shane, Liam, Colin, Christian, Kyle, CJ, Nate, and Leila. Beloved Sister-in-law Nancy Cherry (Canfield). He was also a proud and loving uncle to his Wilcox nieces and nephew Wendy, Eva, Terri and Peter, as well as his Cherry nieces and nephews Kristina, David, Stewart, Greg, Barbara, Kimberly, Karen, and Erika.

Though he was a man who didn’t often express emotion with words, Jim showed his love through action — always helping, always supporting, always showing up. He was a pillar for his family, a steady presence, and a source of quiet wisdom and strength. He loved watching his grandkids play sports, following the Ravens and Orioles, and staying connected to local soccer and the Harford Tech teams he enjoyed cheering for.

Jim will be remembered as a kind, loving, devoted husband, father, grandfather, and uncle who believed in working hard, doing what’s right, and taking care of the people you love. His legacy lives on in his family, his students, and the generations of young athletes he inspired.

A funeral Mass to celebrate his life will be held at St. Stephen’s Church in Bradshaw Maryland on Saturday January 10th at 11AM. In lieu of flowers the family kindly asks that you donate to a local food bank for those in need.

We know this is not goodbye forever — only “see you again.” Jim will be watching over his family, cheering them on as he always did, and waiting to welcome them home when the time comes.

To send flowers to the family, please visit our floral store.