Cynthia Delores Webb

November 01, 1956 ~ June 19, 2023

Cynthia Delores Webb, a dedicated educator passionate about teaching and inspiring young minds, passed away on June 19, 2023, at the age of 66. Cynthia was born on November 1, 1956, in Virginia. She was the daughter of Mary Dolly Webb and Captain William Nathaniel Webb.

Throughout her remarkable career of 45 years with the Boston Public Schools, the last eleven of which she was an Assistant Head of School at Boston Latin School, she touched the lives of countless students. She made a profound impact on the field of education. Her insights and guidance were instrumental in creating a supportive and inclusive learning environment that nurtured both students and staff.

As an educator, Cynthia Webb imparted knowledge and instilled important life values in her students. She believed in fostering a love for lifelong learning, encouraging critical thinking, and promoting empathy and respect among her students. Many former students fondly recall Cynthia’s kindness, patience, and dedication, which left an indelible mark on their lives.

Outside of work, Cynthia enjoyed spending time with her friends. She cherished moments of laughter, shared meals, and created lasting memories. Her warm and compassionate nature made her a beloved presence in the lives of those who knew Cynthia.  

Cynthia Webb leaves behind a legacy that will continue to shape the lives of generations to come. Her passion for education, unwavering dedication, and profound impact on students’ lives will be forever remembered. She will be deeply missed by her family, friends, colleagues, and the countless lives she touched during her extraordinary career as an educator.

Cynthia leaves behind a companion, James Dickey, a brother and sister-in-law, Harry and Glady’s Boger, and many relatives. In lieu of flowers, the family and friends request donations be made to Boston Latin School Association in memory of Cynthia Webb. May Cynthia Webb’s spirit and commitment to education inspire us all to continue her legacy of nurturing young minds and making a positive difference in the world.

Rest in peace, our dear friend “Cindy”. You will be remembered always.

A memorial service to honor and celebrate the life of Cynthia Webb will be held on Thursday, July 27th from 1:00pm-3:00pm at Boston Cremation at 287 Main Street Malden, MA 02148.   


Let the family know you care by sharing this tribute.

2 Condolences

  1. Chris Grammer (BLS 2011-2023) on July 20, 2023 at 1:13 pm

    Ms. Webb is the epitome of the perfect Leader. She NEVER missed the opportunity to greet anyone collegially as well as engage in a friendly, energetic conversation. Any student-centered interactions I had with Ms. Webb she followed up on immediately for the benefit of our kids at BLS. Ms. Webb was always very diligent in assisting with the cleaning up of the Dining Hall between lunches……we made a nice tag team!!! ;-). Cynthia was definitely one of my “go to’s”! Such a positive spirit!!! Cynthia is. and will be missed dearly.

  2. Beverly Faison sneed on July 27, 2023 at 6:27 pm

    So sorry I missed service. Rest in peace Cynthia 💐

Leave a Condolence