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Key West: How Ernest Hemingway and Julius F. Stone, Jr. Shaped a Resort Town

Key West, originally Cayo Hueso, has a long and storied history, which includes Native Americans, pirates, and the US military. The transition from sleepy fishing town to the world-class resort we know today was the result of a now largely forgotten — and contentious — development effort that came about on the heels of the Great Depression.

A colorized photograph overlooking the harborhouse and residential buildings of Key West, as it was in 1900.
Key West, c. 1900. Detroit Photographic Company

Key West has been inhabited dating back to at least 800 C.E. with the Calusa and Tequesta peoples. During this era, the Calusa dominated the west coast of Florida and had political control over the Tequesta on the east coast. There is some speculation about which group maintained the Keys, but archaeologists found pottery sherds from both people groups on the island.  Spanish colonization began in the 1500s, and the little island was designated as a U.S. military seaport in the mid-19th century.

Key West became a permanent settlement in 1822 when John Simonton purchased the small island from Juan Pablo Salas for $2,000. In a stroke of luck, the 1820s saw a boom in American transportation. The Federal Wrecking Act was passed in 1825, which mandated that all wrecked vessels in U.S. waters be taken to a US port of entry. Key West became an official US Port of Entry three years later. Thus, the island went from a sparsely populated backwater to a bustling seaport.

In 1929 and 1934, two famous figures arrived in Key West, Florida, forever changing the island's culture and landscape: notable author Ernest Hemingway came in 1929, and the government official Julius F. Stone, Jr. came in 1934 at the behest of Franklin D. Roosevelt. Though both men had a lot in common—from their Midwest roots to a high level of intelligence—they did not like each other. It was this mutual discord that would change the economy and culture of Key West forever. 

Before 1934, Key West's economy and employment rate were comfortable

enough to allow the population to balloon to approximately 25,000. Then, the Great Depression crushed the local and national economy. Ernest Hemingway had returned to the U.S. from Paris in 1929, actively seeking a secluded place to write. He found his haven in the small town of Key West. The city would feed his fishing hobby and was a touch of the tropics in a temperate climate. 

Julius Stone, Jr. was an organic chemist with a PhD from Harvard who came from a wealthy family. He amassed a fortune in his younger years but lost everything during the 1929 stock market crash. Licking his wounds, he became an administrator during Franklin Roosevelt’s presidency in the 1930s. After President Roosevelt had created the New Deal, Julius Stone Jr. became the head of FERA (Federal Emergency Relief Administration). 

By the time Hemingway had been in Key West for five years, the local economy had all but died. The town was bankrupt because the cigar and sponge workers moved to Tampa, Florida. In 1934, the Key West City Council and the Monroe County Board of Commissioners filed a resolution claiming that Key West was over $5,000,000 in debt. The Coast Guard and the Navy closed their bases, and the island faced massive unemployment. Eighty percent of the island received government support, and the two governing bodies filed a “state of emergency.” 

The presidential black convertable of FDR driving down a main street in Key West, with people standing on the sidewalk.
FDR visits Key West in 1939

After the state of emergency was filed, Julius Stone, Jr. headed to Key West, where he first crossed paths with Ernest Hemingway. Stone, Jr. looked around at the trash in the streets, the shuttered buildings, and the abandoned homes. He faced two choices: relocate the remaining residents to the mainland and convert Key West into a park or try to revitalize the economy.

In addition to the trash and abandoned buildings, Stone, Jr. also saw tropical waters, bougainvillea, and white sand beaches. He thought of transforming the island into a “tropical Bermuda.” A long-standing rumor holds that he was the first to wear Bermuda shorts in Key West, which gave it a laid back appeal. If he were successful, Julius Stone, Jr. would convert Hemingway’s beloved writer’s haven into a resort town, which would, in turn, ruin the serenity that Hemingway craved so badly. This tourism boom marked the beginning of the two men’s rivalry and when “Conchs” ( the name that residents of Key West call themselves) would start calling Stone, Jr. “the Kingfish.”

The Kingfish’s rehabilitation program began by organizing 4,000 locals into the Volunteer Corps to clean up the garbage in the streets and renovate more than 200 homes. The renovations paid for themselves, as the Key West Administration would rent them out while the owners retained their ownership. Once the upgrades were paid for, the rent would go to the homeowners. 

The power of the administration went to Stone, Jr.'s head, and he left a paradoxical mark on Key West. He told the local Key West Citizen,” With a scratch of my pen, I started this work in Key West, and with a scratch of my pen, I can stop it— just like that!” When the New Deal programs dried up, Stone, Jr. practiced law and bought a home on the island's southern tip.


1935 was a pivotal year for Key West. Forty-thousand tourists visited, and hotel reservations grew by 85%. FERA developed a map of 48 tourist attractions, much to the ire of Hemingway. As an added insult, the eighteenth attraction listed was Hemingway’s home. The gawkers were trying to glimpse the famed author at work, so he erected a six-foot brick wall that remains to this day.


Hemingway famously did not want or appreciate any government interference in his life. During the renovation phase, Stone and his bureaucratic FERA had all but taken over Key West and turned it into a tourist trap. Hemingway opposed this idea because it took away his isolation and freedom to work. 1935 also brought the Great Labor Day Hurricane. The powerful storm had wind gusts up to 200 miles per hour and wreaked havoc on Key West, and an estimated 400 people lost their lives. Two hundred victims were World War Two veterans building the Overseas Highway for the New Deal program.

The veterans’ deaths angered Ernest Hemingway the most, and in response, he wrote his most scathing work. Once a World War I correspondent, Hemingway had befriended and socialized with many of the soldiers at the bars of Key West. When enough debris was cleared out of the channels, Hemingway took his boat, the Pilar, to Islamorada and saw the waterways littered with bodies. No friend of the New Deal already, Hemingway wrote an article blaming the federal government for the tragic deaths. 

In his scathing article, Ernest Hemingway stated that the federal government had left the former soldiers there during the hurricane season. Pulling no punches, the article claimed the men were left there because they were politically embarrassing due to psychological wounds obtained during the war. In all honesty, weather forecasting was in its infancy, and not even meteorologists could have predicted the devastating force accurately in 1935. There were evacuation measures in place, but the train was unavailable then.  The hurricane wiped out thirty-five miles of the track, and Key West has not had a train since.

The New Masses, an American Communist Party magazine, asked Hemingway for an insider’s perspective of the hurricane’s destruction. He happily complied, though he never admitted to writing the piece for political change. “Who Murdered The Vets” was published on September 17th, 1935. Although Hemingway was not a communist, the magazine filled his need to rail against the government. The scathing first-hand account of the ravishing storm states in part, “Leaving the veterans to die on Matecumbe Key was no more on (sic.) ‘Act of God’ than leaving them there to live in match-box wooden shacks sweating under the tropical sun for starvation pay.” No one was charged with abandoning the veterans, but the public began advocating that the government be more careful with the lives of its citizens. 

Ironically, after Julius Stone, Jr. left the island in 1937, he and Hemingway lived in Cuba for a while, but there is no indication that their paths crossed again. Tourism slowed down in Key West during World War II but picked up after Harry S. Truman bought a vacation home on the island during his presidency. Today, Key West is a thriving tourist destination and one of the most sought-after vacation spots in the US.

A memorial erected for Stone, Jr. in the Key West Historic Memorial Garden sums up his paradoxical legacy. In part, it states, “He did not always follow the Federal rules, and some of his projects were of questionable legality,” along with, “The programs worked. Key West was on the road to recovery from economic ruin.” While innuendos marred Stone, Jr.’s business practices, he was able to rescue the small island from ruin.

Hemingway left Key West in 1939 and settled in Cuba. His home on Whitehead Street remains a popular tourist attraction, which would surely make him irate were he alive today. The author penned only one novel about Key West, To Have and Have Not. The antagonist in the story is a rigid bureaucratic named Frederick Harrison who claims he is “ of the three most important men in the United States today…”. It is not hard to draw parallels between the character and the real life Julius Stone, Jr., at least through Hemingway’s pen.

Jason Phillips is a travel journalist and food writer based in Florida. When not on the road seeking unique and little-known destinations, he is usually crafting recipes in the kitchen.

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