Richard Nevin “Deej” Webb, Jr., a cherished historian, dedicated educator, author, and community volunteer, passed away on December 21, 2025, at the age of 63. Born on December 29, 1961, in Rio de Janeiro, Brazil, Deej moved to Westport, Connecticut, with his family in 1967.
Deej was a product of Westport’s educational system, attending Saugatuck Elementary, Bedford Junior High, Staples High School and Pomfret Academy. He was a graduate of Vanderbilt University and went on to become a long-time teacher at New Canaan High School as well as the Head of the History Department.
Once retired, Deej dedicated his time as a docent and volunteer at multiple local institutions, including the Fairfield Museum and History Center, the Westport Museum for History and Culture, the Sasquanaug Association and the Lockwood-Mathews Mansion. Deej also enjoyed giving walking tours of Southport Harbor and around Longshore for his Gatsby tour. He served on several nonprofit boards such as Pequot Library, tirelessly working to enhance the appreciation of history and culture in his community.
Deej authored “Boats Against the Current: The Honeymoon Summer of Scott and Zelda,” where he meticulously chronicled F. Scott and Zelda Fitzgerald’s influential time in Westport. His groundbreaking work proposed that Westport, rather than Long Island, served as the inspiration for “The Great Gatsby”. In collaboration with Robert Steven Williams, Deej also co-produced the acclaimed documentary “Gatsby in Connecticut: The Untold Story,” further solidifying his legacy as a passionate advocate for local history.
He is survived by his former wife, Deborah Webb, his sister, Christy Webb Gibson, and twin nieces living in Canada, as well as the Webb and Payne families in the US and Canada and friends both near and far. Deej’s infectious enthusiasm for history, life and sport (Mets, Giants and Jets) touched many. He will be remembered as the life of the party, very often the smartest man in the room and certainly the funniest.
Service information is forthcoming.
For service updates, please visit www.LeskoFuneralHome.com.
Sometimes you meet someone in your lifetime who moves your heart and soul in a way that is inexplicable… a palpable pull… an invincible string… a gravitational orbit… a life force that supersedes earthly understanding… and so it is… so it grows… and so it eternally exists despite realities’ counter voices and life’s conflicting truths, … I will forever miss and deeply love and sky you Richard Nevin Webb Jr. I always did. Do. I Always will … meet me in the Field. 12/21/2025. 🤏🏻❤️🐦⬛🪽♾️😘
I am incredibly sad to read this news. I worked with Deej at New Canaan High School from 2000-2004. We bonded over both growing up in Westport and as proud Vanderbilt graduates. Deej was an AMAZING teacher-the students absolutely loved him, even though his AP US History class that he co-taught with Bob Gardner was famously the hardest class at NCHS! He was warm, funny, intelligent, and very kind to me. He was a big brother of sorts during the time we worked together. I send my heartfelt condolences to his family and friends. May his memory be a blessing.
Deej was a fun presence and a positive intellectual force. I am sorry for his premature demise.