Of Hurricanes and Heroes

The brief, brilliant life of Florida's Overseas Railroad

“No man has any business connected with this work who can’t stand grief.”
- Project manager Joseph Meredith, 1906

In the 1880s, Standard Oil, founded by Henry Flagler and John D. Rockefeller, owned 90% of the global oil refinery market. In 1885, Flagler gave up the day-to-day decisions of running Standard Oil and started building a hotel in Florida. The Ohio-born Flagler, who had never traveled outside the East Coast, became obsessed with Florida just a few years earlier when he had visited Jacksonville when his first wife fell sick. By 1885, he had built a 540-room hotel, Ponce de Leon, in St. Augustine, Florida - the present-day site of Flagler College.

By 1894, he had finished the Royal Poinciana Hotel.

By 1912, Flagler had spent $12 million on hotels, $18 million on railroads, and $20 million on his crown jewel: the Overseas Railroad. Completed in 1912 after seven years and some 200 casualties, the railroad made it possible to take a train from New York City to Key West. Miles of track extended over pure ocean, with no land to see in any direction, an experience writer John Dos Passos described as a “dream journey” and sounds, in all descriptions, like the railroad from Studio Ghibli’s Spirited Away (2001).

In Les Standiford’s colorful and engaging Last Train to Paradise (2002), readers are taken through Flagler’s second act and shown the man’s out-sized influence on the development of modern Florida as we know it. Built from precise prose noting the measurements and materials of viaducts and drenched in feeling with a wealth of firsthand accounts of workers and hurricane survivors, the crux of Standiford’s theme is in the tragedy of the Overseas Railroad itself, an engineering marvel that operated for just over twenty years before being obliterated by the Labor Day Hurricane of 1935.

Standiford tells the tale of how this wonder was built and who built it, and does a satisfying job of offering a framework, but not filling it, with the greatest question of all: why did Flagler build it in the first place?

The Founding of Flagler

In the 1860s, John D. Rockefeller (1839-1937) was in the Cleveland grain business and working off commission. His colleague, Henry Flagler (1830-1913), was doing the same. Flagler’s stepbrother, Stephen Harkness (1818-1888), an apprentice harness maker, built a distillery in 1855 and started extracting crude oil in 1864. When Rockefeller wanted $100,000 (some $2 million today) to start what would become the Standard Oil Corporation, Harkness gave him the funds with the condition that Flagler became a partner. By the late nineteenth-century, Standard Oil owned 90% of the global oil refinery market.

If not for his investments in Florida, Henry Flagler would have been the second-richest person in the world right after his co-founder, John D. Rockefeller. Flagler began his Florida operations in his late fifties and started dreaming of a railroad to Key West in his seventies. He was already a millionaire many times over. As he built his railroad, the media was as supportive of risky tech endeavors as always, nicknaming the project “Flagler’s Folly.”

Flagler rationalized the expenses in public by promising that the Overseas Railroad, would open a new commercial passage for freight trains by connecting the imports from Havana and the Caribbean to Key West. Even when the Overseas Railroad became operational, this never happened. Even before its destruction, Flagler’s most promising predictions never came true. Was this a critical miss by one of the most-respected businessmen in history? Maybe. Flager was eighty-three when the Overseas Railroad opened. I think he just wanted to bluster to make everyone believe in a project that, for Flagler, would be as functional as a pyramid.

All that’s clear in Last Train to Paradise is that he refused to give up. Even after the first hurricane.

Nature vs. Engineer

In total, Flagler laid 366 miles of track linking Jacksonville to Miami and more than 150 miles more connecting Miami to Key West. On the opening of the Overseas Railroad, the Seven Mile Bridge was the longest continuous bridge in the world. The real challenge that Flagler’s crew faced was building railroad tracks that could not only stand in the middle of the ocean while bearing the weight of constant train traffic, but building something that could withstand the impact of hurricanes.

If one reader might get a thrill when Standiford explains that a single arch of a viaduct required 286,00 barrels of cement, 612,000 feet of pilings, 5,000 tons of steel reinforcing arches and 2.5 million timbers, I couldn’t help but keep reading when the antihero of the book, the hurricane, first makes an appearance.

On October 16, 1906, a storm quietly gathered over the Florida Keys overnight. Five miles north, in Coral Gables, residents watched heavy rain pour against the windows. Five miles south, Standiford writes, a storm like “a series of tornadoes” tore through the islands, roaring like “747 engines doubled” and tearing apart homes and flipping cars.

Standiford asks us to imagine a pitcher who can throw a fastball some ninety miles an hour and offers a 1992 hurricane, Hurricane Andrew, as an example of what happened across the Florida Keys in 1906:

Andrew’s winds were running somewhere between 150 and 175 miles an hour. A baseball weighs five ounces. Now try to imagine taking a hurricane-tossed, five-pound clay roof tile in the face. Or think of a jagged hunk of ripped-in-half tin sheeting, ten pounds of it, let’s say, Frisbeeing along at 150 miles per hour - try to conceive of what that might do, meeting the human body.

More than 125 railroad workers would be left dead. The wind and water carried many others to far-flung destinations that would probably make compelling memoirs in themselves:

• 49 were pulled from the water after the hurricane near the Keys

• 24 disembarked in Mobile, Alabama, rescued by a British steamer

• 1 appeared off a freighter in Mobile

• Another in Liverpool

• Others emerged in Gavelston, New York, London, and Buenos Aires

To the engineering challenge of the arch to span the ocean, Flagler wrote to the engineers:

“It is pretty simple, all you have to do is build one concrete arch, and then another.”

To a report about the tragedy of 1906, Flagler wrote:

“Go ahead.”

The legacy that the Overseas Railroad would leave behind, Flagler had long decided, was bigger than him - and most certainly bigger than everyone else working on it. But what’s a legacy when it’s only temporary?

Find out on Monday for the epic conclusion of whether Flagler’s legacy was pointless… or if any legacy isn’t pointless in the wrong perspective. If you want more Florida Keys content in the meantime (who doesn’t?), read Litverse’s analysis of Hemingway’s 1937 To Have and To Have Not.