Ninety-nine years ago, Scribner Books published then 28-year-old F. Scott Fitzgerald's third novel, The Great Gatsby.
Set in the 1920s on Long Island, the book follows Nick Carraway. He witnesses a tragic love triangle unfold between his cousin Daisy, her abusive husband Tom Buchanan, and Carraway’s rich, enigmatic, and charming neighbor, Jay Gatsby. Despite the book's initial poor sales, The Great Gatsby later received widespread critical acclaim and would go on to often be heralded as the Great American Novel for its universal themes on the American Dream, class, and love.
Years after its publication, Gatsby’s Roaring Twenties tragedy would be read in thousands of schools across the country, adapted into four films, and performed on numerous stages, including a recent return to Broadway last month.
The Great Gatsby, like many of F. Scott Fitzgerald's novels, is based on his own experiences. Long Island claims the book is based solely on Great Neck (called West Egg in the novel).
Or, perhaps where Fitzgerald and his wife Zelda lived in Westport, Connecticut.
“It had such an incredible impact on their lives that Westport shows up again in The Beautiful and Damned,” explained Richard Webb Jr. “It shows up in The Great Gatsby. It shows up in Zelda’s only play, Scandalabra. It shows up in five short stories that Scott wrote. It shows up in her only book, Save Me the Waltz.”
Gatsby in Westport
A Westport native, Webb co-produced the award-winning 2020 documentary Gatsby in Connecticut: The Untold Story alongside Against the Grain Communications Marketing agency owner Robert Steven Williams. In 2018, the two co-wrote the documentary’s companion book Boats Against the Current: The Honeymoon Summer of Scott and Zelda: Westport, Connecticut 1920. Webb first discovered Westport’s relation to Fitzgerald’s writing as a kid while reading The Beautiful and Damned. He realized most of the events transpiring in the book, and later Gatsby, took place at roads and locations he grew up along.
Following the successful release of Fitzgerald's first novel, This Side of Paradise, Scott married 19-year-old Zelda Sayre in April 1920. The two then spent their five months as a married couple in a small house along the coast of Long Island Sound in Westport. Here, the two often celebrated by driving to Long Island and New York City for parties, shopping, and drinking. But the two weren’t alone on this coastline.
A few miles away stood a 175-acre mansion owned by the mysterious millionaire Frederick E. Lewis. An equestrian and car enthusiast, Lewis was the practical definition of a partier, often having hundreds of people come far and wide to his residence.
In 1917, Lewis hosted one of the largest parties in the state in the form of a Red Cross and Allied War charities drive. Hundreds of high-class guests were entertained with circus animals, live music, plane rides, a reenactment of a horseback battle between cowboys and Native Americans, and even a performance from master illusionist Harry Houdini in a chained box lowered into the Long Island Sound. This single party raised over $50,000 for the war effort.
Zelda Fitzgerald was quickly banned from these famous parties after becoming excessively drunk on one occasion. Zelda was still allowed to swim on the premises’ coast, however. Scott Fitzgerald didn’t interact with Lewis directly, but he often commented on his extravagant parties in his journals.
Lewis, his parties, and his coastal estate are believed to be one of the major influences on Jay Gatsby. Meanwhile, the small Fitzgerald house is believed to influence Carraway's house, especially because of its location near Lewis’ mansion. That would make Carraway based on F. Scott Fitzgerald during his time at Westport.
“Scott Fitzgerald famously said, ‘All my characters are F. Scott Fitzgerald,’” Webb said. “So he’s Nick Carraway in the book.”
Daisy Buchanan is based in part on Zelda Fitzgerald but was primarily based on Ginevra King, a Chicago socialite and Scott's first love, who rejected him.
Aspects of the Lewis estate are directly mentioned in The Great Gatsby. Chapter Five reads, “Instead of taking the shortcut by the Sound, we went down to the road and entered by the big postern.”
This is in reference to the gateway that leads to the windy road toward Lewis’ mansion.
“If it wasn’t for the mist we could see your home across the bay,” Gatsby said. “You always have a green light that burns all night at the end of your dock.”
According to Webb, this is in reference to a green light found on a dock across from Lewis’ estate in Long Island Sound.
The move to Long Island
The Fitzgeralds were nomads — never staying in one place for too long. Five months after their stay at Westport, the Fitzgeralds moved to Great Neck on Long Island in 1922 and lived there for a year and a half. A very different residence from the Westport house, their new 5,174-square-foot, Mediterranean-style mansion allowed them to embrace the lifestyle of both Lewis and Gatsby.
However, most of their writing would still highlight their experience in Westport alongside new elements from Great Neck.
“Great Neck is definitely in the novel. it’s just that, combined with Westport, it's a beachy blend,” Webb explained. “They lived for a year and a half in Great Neck but they never wrote about the house that they lived in… There’s never been one particular house in Great Neck that’s been pointed out as THE Gatsby House.”
Several Long Island mansions have been sold for millions of dollars as “The Gatsby House” or as Gatsby-esque. In February, the 92-acre Erchless Old Westbury estate was put on the market for $23 million. However, this property was built in the 1930s, not the 20s.
F. Scott Fitzgerald began writing Gatsby in Great Neck, but most of it was written after the family moved to France in 1924. It was here where elements of Great Neck and Westport merged into West Egg.
“And the other thing why Great Neck, well, he clearly set the book in Long Island, but he wrote most of Gatsby while he was in France,” Williams explained.
“He was drinking heavily at the time and if you think about it as you’re writing fiction and you’re drawing upon your experiences, which we’ve already proved that he was doing, if your on the Northside of Long Island Sound or the Southside of Long Island Sound, you’re taking the train from Great Neck into the city, you’re taking the train in from Westport into the city, both of which we know he did, that it could be easy to mix up some of these things and that’s why we call it this blend and why we know that there were errors in the book because he mixed things up.”
Despite the Fitzgeralds' frequent and extravagant moves, they often looked back on their summer in Westport for inspiration.
“1920 was this magical year for them,” Williams said." They get married, he becomes an instant success, they’re both like international pop stars… They really didn’t get to know each other until they got married because it was a shotgun marriage.”
Zelda previously called off their wedding because Scott struggled to attain literary success at first. It was only after Paradise’s success that Zelda had faith in him that he could support her. In a way Zelda was similar to Daisy in that she was attracted to wealth and popularity.
“It all happened here in Westport, and if you think about what sticks with you, it’s those seminal moments,” Williams added. “That’s really what’s so magical about the time here. It’s not the length, it’s the importance in terms of their life… Westport was the happiest they were.”
Amid the Great Depression and literary struggles, the Fitzgeralds' lives would deteriorate. F. Scott developed alcoholism, and Zelda developed schizophrenia. Most of their funds would be spent on Zelda’s psychiatric treatment and their daughter Scottie's school expenses. F. Scott Fitzgerald died in 1940 of a heart attack. Zelda Fitzgerald later died from a fire in a psychiatric hospital in 1948.
Gatsby today
The Great Gatsby would receive newfound critical and popular appeal during World War 2 after the Council on Books in Wartime sent thousands of copies of Fitzgerald's writing to soldiers. Since then, The Great Gatsby has remained in publication and is read annually by millions of readers.
Lewis’ estate later became The Inn at Longshore and the Longshore Club Park Golf Course. The Fitzgerald’s Westport home is still a 1758 Colonial home today.
Webb and Williams have strived to have the Town of Westport mark, preserve, and even purchase the house for historical and educational purposes. They warn this leaves the house in danger of being torn down by a potential developer.
Onlookers may see a historical sign attached to the house with its construction date and an inscription that reads, “F. Scott & Zelda Fitzgerald (1920).”
Webb hosts seasonal tours of both the Longshore Inn and the Fitzgerald house in Westport. All proceeds from the tour go towards the Westport Museum for History and Culture.
The Great Gatsby will turn 100 years old on Thursday, April 10, 2025.
