Category Archives: History

Richard “Deej” Webb, Jr. — a Westport native, teacher and historian who grew up near Longshore, then turned a fascination with F. Scott Fitzgerald’s summer here into a book and documentary that claimed this area inspired “The Great Gatsby” — died on December 21. He was 63.

Deej was born in Rio de Janeiro, Brazil, but moved with his family to Westport at 6. He attended Saugatuck Elementary, Bedford Junior High and Staples High Schools, and Pomfret Academy.

After graduating from Vanderbilt University, he taught social studies — and then headed the department — at New Canaan High School.

Richard “Deej” Webb

Though the Westport of Deej’s youth looked quite a bit different from that of the several months that F. Scott and Zelda Fitzgerald spent in Westport, the area around Longshore and Long Island Sound were recognizable.

The couple rented a home — still standing — on Compo Road South, just north of what is now the Longshore entrance drive.

Deej meticulously researched the real estate and topography of the town-owned club, which in 1920 was the personal estate of the very wealthy Frederick E. Lewis.

Believing that Fitzgerald’s view of the estate, and the Sound beyond it, influenced the author’s view of protagonist Jay Gatsby, and his lifestyle — not, as traditionalists believed, Long Island — Deej pored over newspaper and magazine stories, other historical documents, and Fitzgerald’s own writing, to prove his point.

Deej then collaborated with Robert Steven Williams. They co-produced a documentary: “Gatsby in Connecticut: The Untold Story.” It used Deej’s findings — and archival photos — to make the same claim about Westport’s role.

The pair also published a companion book: “Boats Against the Current: The Honeymoon Summer of Scott and Zelda.”

Celebrating “Gatsby Day” in Westport in 2019 at the Fitzgerald house on Compo Road South are (from left) Robert Steven Williams, 1st Selectman Jim Marpe, Deej Webb, and Westport Museum of History & Culture executive director Ramin Ganeshram. (Photo/Dave Matlow)

After retiring from teaching, Deej served as a docent and volunteer at the Westport Museum for History & Culture, Fairfield Museum & History Center, the Sasquanaug Association and Lockwood-Mathews Mansion. 

He gave walking tours of Longshore and Southport Harbor. He also served on nonprofit boards, including the Pequot Library.  

Deej was also an avid New York Mets, Jets and Giants fan.

He is survived by his former wife, Deborah Webb; his sister Christy Webb Gibson; twin nieces in Canada, as well as the Webb and Payne families in the US and Canada. 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.

Information on services will announced soon.

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In 2018, “06880” profiled Deej Webb’s work on F. Scott Fitzgerald and “The Great Gatsby.” We wrote:

When Richard “Deej” Webb was 14, he read “The Great Gatsby.”

Through his bedroom window across from the Minute Man monument, he could see the house that — decades earlier — F. Scott and Zelda Fitzgerald once rented.

In between was Longshore. Deej caddied, biked and ran there. He knew every inch of the property well.

In 1996, when Barbara Probst Solomon wrote a New Yorker story claiming that Westport — not Great Neck, Long Island — was the inspiration for Gatsby’s “West Egg,” Webb was fascinated.

By then he was teaching US history at New Canaan High School. But the 1980 Staples graduate’s heart — and home — remained here.

Webb studied Solomon’s theories. He researched Longshore, and environs. Convinced she was right — and that Westport, in fact, influenced both Fitzgerald and his wife far more than anyone realized — Webb spoke to whomever he could.

Many Fitzgerald scholars and fans were interested. Most Westporters, he says, were not.

In 2013 Webb participated in a Westport Historical Society roundtable examining the town’s literary past. Organizer Robert Steven Williams — a novelist — asked Webb if he’d like to collaborate on a documentary about Fitzgerald’s time here.

The film will be shown on public television this fall. A companion coffee table book — “Boats Against the Current” (taken from a famous “Gatsby” line) — will be published next month.

The book cover shows the iconic photo of F. Scott and Zelda Fitzgerald, in front of their South Compo house. 

“Boats” is thoroughly researched, lavishly illustrated, and immensely educational. It should be required reading for every Westporter.

Webb and Williams took Solomon’s original thesis — that Fitzgerald’s home next to the 175-acre estate of reclusive millionaire Frederick E. Lewis (now Longshore) informed not only the author’s physical description of Jay Gatsby’s mansion, but also much of the novel’s emotional power — and expanded it to encompass nearly the entire Fitzgerald ouevre.

In 1920, his first book — “This Side of Paradise” — had just been published. Fitzgerald was making great money. He and Zelda were newly married — and kicked out of New York’s finest hotels, for debauchery.

Westport was their honeymoon. It was also their first home. Here — especially at Lewis’ next-door estate — they enjoyed celebrity-filled orgies. And they skinny-dipped at Compo Beach.

Zelda at Compo Beach — before (or after) skinny-dipping. (Photo courtesy of “Boats Against the Current”)

Their experiences and memories — along with the town’s sights and smells — all became part of “Gatbsy”; of “The Beautiful and the Damned”; even of Zelda’s paintings, Webb says.

In fact, he adds, “Westport shows up in their works more than any other place they lived.”

The back story of Lewis — a descendant of one of the wealthiest families in American history — is particularly fascinating. He’s not a familiar name. But his parties at what later became Longshore — which the Fitzgeralds surely must have attended — were beyond legendary. One even featured Harry Houdini. (Yes, he performed an escape trick right there.)

His and Williams’ painstaking work has been accepted by many Fitzgerald scholars, as well descendants like granddaughter Bobbie Lanahan.

Robert Steven Williams (left) and Richard “Deej” Webb flank the Fritzgeralds’ granddaughter Bobbie Lanahan.

The New York Times recently published a story on Webb and Williams’ project. The international attention was gratifying.

But the duo have a more local concern too.

All around town — including Webb’s boyhood Compo Beach neighborhood — homes are being torn down. Big new houses are replacing older ones with important  histories.

Webb and Williams worry the same fate may befall Fitzgerald’s house. And, they fear, few people will care.

The current owners, Webb says, “are fantastic. They’re well aware of the significance, and treat it with great respect.”

But there’s no assurance a future owner will not tear the 1758 structure down.

F. Scott and Zelda Fitzgerald slept — and partied — here, on South Compo Road.

There is only one museum in the world dedicated to F. Scott and Zelda Fitzgerald. It’s in Montgomery, Alabama, where he wrote portions of 2 novels.

Wouldn’t it be wonderful, Webb and Williams ask, if at some point the town could buy the house, and turn it into a “Fitzgerald Center”?

“Sometimes Westport has amnesia about its history,” Webb says. “It’s an incredible past. It’s hard to find an American town that has more. But it’s disappearing in front of our eyes.”

Of course, as a history teacher — and amateur historian – Webb knows the one thing that never changes is change.

When the Fitzgeralds arrived in 1920, he says, “farmers in  Westport worried about all the New Yorkers coming in.”

With their lavish parties and skinny-dipping orgies, those newcomers had a new way of doing things.

One hundred years later — thanks to F. Scott and Zelda Fitzgerald — those Westport days live on.

And — thanks to Deej Webb and Robert Steven Williams — they’re memorialized forever.