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A Man, a Plan and a Span: Henry Flagler and the Overseas Railroad



The Key West Extension of the Florida East Coast Railroad was known in its time as

“The Eighth Wonder of the World”. It ranked with the Panama Canal as one of the

great engineering projects of the new century; a demonstration of America’s

burgeoning confidence, technological ingenuity and “can do” spirit that would soon

be further expressed in the creation of other marvels such as the Golden Gate

Bridge, Hoover Dam and the Empire State Building. On a more practical note, the

Overseas Railroad directly linked the island boomtown of Key West to Miami and the

rest of Florida, and was the culmination of Henry Flagler’s dream of providing reliable

and fast transportation throughout the state.



A Dream Awakens



If anyone could see such an enormous project through to completion, it was Henry

Morrison Flagler. Born the son of a minister from Hopewell, New York in 1830,

Flagler was a man of profound determination and vision who had risen to prominence

as John D. Rockefeller’s right-hand man in the company that would become Standard

Oil. By the early 1870s Standard Oil was America’s leading oil producer and its

principals were looking to invest their newly made millions in other business

ventures. In 1878, Flagler found himself in Florida seeking refuge and respite from a

typically harsh New York winter. Flagler saw in south Florida’s swaying palms and

pristine beaches a virtual paradise that needed only sufficient infrastructure to reach

its full potential.



Henry Flagler was the kind of man who was blessed with the gift of being able to see

the “big picture”. This talent served him well at Standard Oil where he oversaw the

establishment of the many supporting industries needed to facilitate the flow of oil

from the company’s fields. One of these essential cogs was the railroad, without

which oil could not be transported to refineries - these being the days before

pipelines and modern road networks. As Flagler enjoyed his honeymoon with his new

wife Ida in St. Augustine, Florida, he could see that an efficient railroad network and

upgraded visitor accommodations were crucial to Florida’s success as a vacation

paradise. Flushed with excitement and buoyed with optimism, Flagler resigned his

position at Standard Oil and systematically began to turn his dream into reality.



Big plans require deep pockets, and Henry Flagler’s pockets were very deep indeed

thanks to his stint at Standard Oil. After moving his household to St. Augustine and

buying several hotels there, he set about upgrading them to the level of the very

best French Riviera resorts. It was here that he ran into another problem: building

supplies and materials were only trickling into St. Augustine on Florida’s rudimentary

railway system. Once again Flagler dug deep, this time purchasing the Jacksonville,

St. Augustine & Halifax River Railway; the St. John's Railway; the St. Augustine and

Palatka Railway and the St. Johns and Halifax River Railway. By 1889 these various

lines had been linked and consolidated, providing travelers and businesses with a

reliable rail link from Jacksonville in the north to Daytona in the south. Flagler built

stations, depots, hotels and even churches and hospitals along the route that

became the nuclei of new towns like Titusville and West Palm Beach. By 1895 the

“Florida East Coast Railway Company - Flagler System” (known as the “FEC” for

short) was officially incorporated.



Rolling South, and Beyond

The seeds Flagler had planted were beginning to bear fruit as the 19th century drew

to a close. Palm Beach boasted glittering resort palaces like The Breakers Hotel and

the Royal Poinciana Hotel that attracted high rollers, captains of industry and the “jet

setters” of the day from either coast and from across the Atlantic. Florida’s building

boom shifted into high gear and Flagler was no longer alone in his efforts to improve

the Sunshine State’s attractions and infrastructure. In response to interest from

landowners and investors in the southernmost part of the state, the FEC continued to

extend its rails southward, reaching the frost-free shores of Biscayne Bay by 1896.

Flagler saw in the unincorporated land at the line’s terminus an enticing opportunity

to build a residential, entertainment and industrial center that would act as an

economic engine for the entire southern part of the state. As before, Flagler got the

ball rolling by improving the harbor, laying down electric, water and sewer lines

beneath brand new streets, even subsidizing the new town’s first newspaper. It was

fitting that the new town should bear the name of the man responsible for its

establishment but Flagler was modest to a fault. Instead, he suggested to the town’s

444 inhabitants that they choose “Miami”, the name of a former plantation founded

on the south bank of the Miami River. The name was approved and Miami was born.



In the year 1900, Henry Flagler reached his 70th year and could certainly be forgiven

for wanting to slow down a little, perhaps to settle down and enjoy his retirement in

the state where he was responsible for so much development. Flagler wasn’t your

average septuagenarian, though, and even in his old age he could still be inspired

into action. The next spark that set Flagler’s imagination ablaze was president

Theodore Roosevelt’s announcement that construction would soon begin on the

Panama Canal. This was no small undertaking. A French-sponsored attempt to build

a canal through the Isthmus of Panama in the 1880s was abandoned after more than

20,000 workers had perished from yellow fever and malaria. Roosevelt, however,

embarked on a disease eradication program he believed that, combined with the

latest gasoline-powered construction machinery, would surely achieve success.

Flagler saw that disease and technological shortcomings were no longer obstacles to

a plan he had been mulling over since the FEC had ceased its southern expansion a

decade earlier: an extension of the railroad south past Miami, “island hopping” all the

way to Key West.



Spans Across the Ocean



Key West lay 150 miles southwest of Miami at the tip of the long chain of islands and

sandbars that extended in a curving arc into the Gulf of Mexico. First discovered by

Spanish explorer Ponce de Leon in 1521, the island of Key West was claimed for the

United States in 1822 by Matthew Perry. Perry would achieve lasting fame 30 years

hence when he led a flotilla of “Black Ships” to force the opening of Japan to

American trade. By the end of the century, Key West had become a thriving town of

20,000 with a busy deep-water harbor and an economy based on salt making,

marine salvage and cigar manufacturing.



Henry Flagler recognized that a rail connection to Key West would provide profit from

the increased trade expected once the Panama Canal was opened to inter-ocean

traffic. So it was that in 1905, construction began on a project that seems wildly

audacious even from our viewpoint a century later: the Key West Extension of the

Florida East Coast Railway. Panned by some as “Flagler’s Folly”, the proposed

extension would need to cross the 128 miles between the end of the Florida

peninsula and Key West, most of it being the warm waters of the Gulf of Mexico.

Progress was slow but steady with construction pausing occasionally as hurricanes

blew through the Keys as they are won’t to do. Thousands of men toiled for over 7

years on the Extension, building a stretch of Italianate bridges and causeways that

slowly but surely spanned the wave-tossed distances between the Keys. Finally in

the spring of 1912, the first train from the Florida mainland pulled into the Key West

station. Proudly standing on the balcony of the observation car upon arrival was

none other than Henry Flagler, who would not have it any other way. Goodbye

“Flagler’s Folly”, hello “Eighth Wonder of the World”. Sadly, on May 20th of 1913 at

the age of 83, just over a year after completing the greatest of his many triumphs,

Henry Flagler died following a fall down the stairs at Whitehall, his Palm Beach

estate.



From Triumph to Tragedy



A golden era in train travel ensued as elegantly appointed passenger trains plied the

Overseas Railroad to and from America’s new southernmost point. Effusively

illustrated FEC advertisements prominently featured the lines signature arching

bridges and enticed vacationers with tag lines like “Every Day a June Day, Full of

Sunshine - Where Winter Exists in Memory Only”. As Floridians know only too well,

unfortunately, Mother Nature can be capricious, especially as those sunny June days

fade into the unsettled dog days of August that portend the start of hurricane

season.



No less than five hurricanes had struck the Florida Keys during the Extension’s

construction, including one particularly vicious storm in 1906 that killed several

hundred workers. Everyone involved knew what dark beasts slouched towards the

Gulf coast each year as the days began to shorten. Perhaps a comparison can be

made to the designers of the Titanic who were fully aware of the silent mountains of

ice the great ship would be expected to encounter in the frigid waters south of

Greenland. They planned for any eventuality by incorporating a system of watertight

bulkheads into the Titanic’s hull. The ship could withstand the flooding of four

bulkheads, but not the five breached by the iceberg. The Key West Extension was

built to withstand hurricane-force winds, but the Labor Day Hurricane of 1935 was no

ordinary hurricane. This was a Category 5 monster. Residents of the Keys had only

an inkling of what was coming their way - both hurricane forecasting and radio

broadcast news were in their infancy. Even more oblivious were the more than 350

World War I veterans on Lower Matecumbe Key who had been posted there to build

bridges for the WPA (Works Progress Administration). It is difficult to imagine the

horrific ordeal suffered by these men as shrieking 160mph winds whipped away their

flimsy shelters and blasted beach sand with a force powerful enough to peel skin.



The crowning blow was the 16-foot storm surge that washed away anything not

already blown away by the winds, and that included the rescue train sent down the

Extension by the FEC from which only the engine remained upright and on the rails.

Among the more than 400 people who perished as a direct result of the storm were

259 veterans. To this day, the Labor Day Hurricane of 1935 remains the most

powerful cyclone ever to strike the US mainland.



Death and Re-Birth



In the aftermath of “The Storm of the Century”, as it would be come to known, FEC

inspectors discovered that some sections of the Overseas Railroad’s causeways were

heavily damaged and others were completely destroyed. The line had suffered from

financial woes after the Stock Market Crash of 1929 and could not afford to repair

the Extension. The crumbling remnants of the once grand gilded-age showpiece that

had cost $40 million to build were sold to the State of Florida for a mere $640

thousand. The State immediately set about re-establishing the land link to Key West,

but this time it would be roads and not rails that spanned the seas. Many of the Key

West Extension’s surviving bridges and causeways were utilized to form the

Overseas Highway that opened in 1938. The highway was beginning to show its age

by the 1970s and most of it was rebuilt over the following decade. Driving down US1

to Key West is still an exhilarating experience. One can imagine the excitement (and

not a little trepidation) felt by passengers riding the Overseas Railroad in those

bygone days.



Looking back at the Key West Extension of the FEC and its catastrophic demise, one

must resist the temptation to blame the tragedy on the unbridled optimism so

characteristic of the early years of the 20th century. Again we can recall the

“unsinkable” Titanic (which coincidentally sank the same year as the Key West

Extension was completed), whose watery grave serves today as a monument to

mankind’s hubris and a misplaced faith in the infallible power of technology. Have we

learned anything in the 70 years since the Labor Day Hurricane dashed Henry

Flagler’s dream to the depths? Perhaps not - hurricanes continue to frustrate the

best-laid plans of men and reduce his works to dust. The deadly toll taken by

Hurricane Katrina and the flooding of New Orleans show that there are still limits to

what humanity can accomplish when faced with the power of nature.









Recommended reading:



Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of

the Railroad that Crossed an Ocean

Hardcover: 288 pages

Publisher: Crown; 1st edition (September 2002)

ISBN: 0609607480



Storm of the Century: The Labor Day Hurricane of 1935

Hardcover: 320 pages

Publisher: National Geographic (August 1, 2002)

ISBN: 0792280105



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