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Authors: Les Standiford

Last Train to Paradise

BOOK: Last Train to Paradise
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Henry Flagler and the Spectacular Rise and Fall of the Railroad That Crossed an Ocean


This book is dedicated to the memory of the hundreds of “vets” who lost their lives during the Labor Day hurricane of 1935, as well as to the hundreds of Keys residents—men, women, and children—who also suffered and died that day.

I would like to express special thanks to Bernard Russell for sharing his memories of the ’35 storm so candidly; to Scott Waxman, who envisioned what this book could be; to Robert Mecoy and Emily Loose, who believed in it from the beginning; and to Kimberly, Jeremy, Hannah, and Zander for their boundless support and patience.

Special thanks is also due a number of individuals who lent invaluable support and assistance to this enterprise, most prominent among them: John Blades, director of the Henry Morrison Flagler Museum in Palm Beach, Dr. Robert Gold, Catherine O’Neal, and, especially, Rebecca Callahan.

I am also indebted to Steven Leveen and Dr. Bill Beestig for their close reading and fact-checking of this manuscript.

And the usual inexpressible gratitude goes to James W. Hall and Rhoda Kurzweil, who looked over my shoulder all the way along, correcting, suggesting, and, as always, reminding me of the little blue engine that could.

Praise for

Last Train to Paradise

by Les Standiford

“A mesmerizing account of Gilded Age titan Henry Flagler and his extraordinary dream to build a railroad across the sea. Les Standiford has written a detailed and startling history of the man behind the dream, the visionary engineers who insisted—against all odds—that it could be done, and the thousands of workers who spilled their blood making the dream into a reality. Henry Flagler’s quest to build an overseas railroad from the tip of the Florida mainland to Key West has all the elements of a classic Greek tragedy, and Les Standiford has captured both the man and his times with pitch-perfect grace.”

—Connie May Fowler, author of
Before Women
Had Wings
When Katie Wakes

“A brisk, breezy narrative of Flagler’s dream . . . Standiford employs his novelist’s skills in this rollicking story of robber-barony.”

Plain Dealer

“This is a wonderfully told tale, a strange and compelling story about a strange and compelling part of the world. With sharp, evocative reporting, the book captures an era, the Florida landscape, and the very human dream of doing the impossible.”

—Susan Orlean, author of
The Orchid Thief

“Absorbing, you-are-there detail . . . Standiford sticks close to his subjects—Flagler, the railway, the hurricanes—and the story goes straight to its destination.”

Miami Herald


Roanoke Times

“If Henry Flagler’s railroad from Miami to Key West was the eighth wonder of the world, Les Standiford’s bravura work of nonfiction is a wonder in its own right. The triumph is in the telling of this deeply American story in which a hard-nosed tycoon becomes a hopeless dreamer trapped in a courtship of steel, sky, and water as beautiful as it is doomed. Technology challenges nature to a duel, and the only real winners are the lucky readers of this suspenseful, elegant, breath-taking volume.”

—Madeleine Blais, author of
Uphill Walkers: Portrait of a Family

“As mesmerizing and heart-stopping as [Standiford’s] best fiction . . . Read as history, biography, or simply high-voltage entertainment,
Last Train to Paradise
is a flawless marriage of scholarship, historical commentary, and art.”

St. Petersburg Times

Last Train to Paradise
is an extraordinary achievement. A nonfiction book as exciting and finely written as a first-rate novel, with the narrative drive of a locomotive. Les Standiford has seamlessly interwoven three fascinating stories: the rise and fall of the richest man in America, a chronicle of the most complex engineering project ever, and the story of the most powerful storm ever to blast our coastline. Throw in Ernest Hemingway and some of the most dramatic scenes of the chaos of a hurricane ever written and you’ve got one hell of a spectacular book.”

—James Hall, author of
Rough Draft
Under Cover of Daylight

“Standiford brings to life [a] man and his obsessive project. . . . It’s a story of high drama filled with nature’s fury, and the resolve of one man to accomplish what others said could not be done.”

Fort Lauderdale Sun Sentinel

“Everyone who has ever driven U.S. 1 should read this book, because afterward the ride will never be the same. . . .
Last Train to Paradise
is a book full of surprises and insight.”

Key West Citizen

“A remarkable account of one man’s dream that ended in disaster.”



Tampa Tribune

“The virtues of Standiford’s book include an ability to make us see both Flagler and his railroad with fresh eyes. . . . Linking the fearsome power of nature to the power of an American titan’s wealth and dreams in the age of Manifest Destiny, Standiford forges a tragedy in the classic sense. . . . We have Standiford’s narrative gifts, too, in this book to remind us that for great American stories of sweeping vistas, visionary titans, and frontier catastrophe, we don’t have to look only to the tales of the West. . . . Greatness both in achievement and storytelling can be found.”

Orlando Sentinel

And on the pedestal, these words appear: “My name is Ozymandias, King of Kings, Look on my Works, ye Mighty, and despair! ”Nothing beside remains. Round the decay Of that colossal Wreck, boundless and bare The lone and level sands stretch far away.

—Percy Bysshe Shelley

Ah, but a man’s reach should exceed his grasp, or what’s a heaven for?

—Robert Browning

Author’s Note

and historian J. Frank Dobie once lamented that most historical research amounts to the carrying of the same old bones from one grave to another. And as I have gone about the research and the writing of this book, I have been mindful of Dobie’s words every working day. The fact that able explorers have scouted the most promising grave sites in advance can be helpful, of course; but if all the artifacts have been unearthed and duly noted, then it might seem there is little useful work left to do.

Indeed, others have written well and truly of Henry Morrison Flagler and his remarkable life. His part in the creation of Standard Oil has been ably documented, even if many remain unaware that he and John D. Rockefeller were once coequals in that process. And other writers have credited Flagler—through the building of the Florida East Coast Railway and the founding of most of the state’s best-known cities, including Miami—with the veritable creation of Florida as we know it today.

Even the story told here, of the building of the Key West Extension to Key West, “the railroad that crossed the ocean,” is not an unknown one, at least in general outline, to Floridians who have lived in the shadows of that great undertaking, known someone who helped in its building, driven by car along the route, or read one or another of the many monographs and newspaper articles and personal accounts connected to it.

But if we are talking about the disinterment of old bones here, then this telling of the Key West Extension’s birth, and its demise, aspires at the very least to lay them out in a common grave. And if doing so enhances anyone’s appreciation of the magnitude of Flagler’s mammoth, star-crossed undertaking, then it has been worth it.

By anyone’s estimation, Henry Morrison Flagler accomplished a number of remarkable things in his eighty-three years, but it is the thesis here that nothing he did, not even the creation of Standard Oil—the ultimate symbol of corporate wealth and power—can compare to the laying of that last stretch of Florida East Coast Railway track.

Building Standard Oil required great business savvy, a certain measure of ruthlessness, and not a small amount of luck. Building a railroad across an ocean required extraordinary vision, effort, perseverance, and sacrifice. The former qualities, which Flagler used in abundance during the first half of his life, seemed far less central to the second half. Certainly whatever luck visited the undertaking of the railroad across the ocean was bound to be bad.

No one today would undertake what Flagler did, not in this bottom-line world. Nor would they undertake Chartres or Notre Dame, for that matter. Dreaming up a railroad to Key West is the stuff of another era, and its undertaking is the work of another kind of man.

In the impossibleness of what was once called “Flagler’s Folly” is also its magnificence. In its final undoing is the significance of tragedy.


End of the Line


Labor Day Weekend, 1935

At about four o’clock in the afternoon on Labor Day Saturday in 1935, Ernest Hemingway, by then one of Key West’s most notable residents, thought it time to knock off work on weaving together what an editor had called “those Harry Morgan stories,” an undertaking that would eventually be published as a novel titled
To Have and Have Not.
He left his studio, went into the kitchen with its high, built-to-Papa cabinet tops, to pour himself a drink, then walked out onto the spacious porch of the two-story home on Whitehead Street that he and his second wife, Pauline, had bought in 1931.

The day’s work had been good. Now he intended to wind down and have a look at the evening paper.

The weather was typical for late summer in Key West: the temperature in the high eighties, the humidity about the same, but the skies were clear, and there was a sea breeze sweeping over the mile-wide island to soften the heat, especially in the shade of a broad front porch.

It was a newfound pleasure for Hemingway to indulge himself in such a simple fashion, even in his own home. The year before, a zealous Federal Emergency Relief Act Administration official had published a pamphlet intended to boost tourism, listing Hemingway’s home among the top twenty-five attractions on the island of some twelve thousand souls.

Though Hemingway well understood the value of cultivating a certain mystique, it had nonetheless galled him to find himself, on the way to or from his workroom on the second floor of a then-unattached outbuilding, staring back at a queue of gawking visitors on the other side of the chain-link fence that protected his property. Thus, only a few days before, and after much wrangling with a city bureaucracy that considered it an eyesore, work had been completed on a stone wall that now marched about the three open sides of the house’s corner lot, giving him some measure of privacy at last.

It is easy to imagine Hemingway in a reasonably affable mood that afternoon. “Now that I’ve gone private,” he’d remarked to his longtime handyman, Toby Bruce, once the wall was up, “they might even take me off the tourist list.”

And because it was the off-season, there would be no crowds in Sloppy Joe’s Bar to annoy him during his late-night rounds. Nor had the “mob”—as he sometimes referred to the annual coterie of friends and hangers-on from the North—arrived to lure him from his work to go on fishing expeditions out to the nearby Gulf Stream or Dry Tortugas, or to an endless round of parties there on land.

Earlier that summer he had turned in a completed manuscript of
The Green Hills of Africa,
which he privately considered his best writing since
Death in the Afternoon.
With publication scheduled in October, Hemingway was eager to see if the public’s approbation matched his own. Though he’d had similar hopes for the bullfighting book when it was published in 1932 and had been disappointed by the decidedly mixed opinion of the critics, he was certain he would receive his due this time.

He’d received a nice little bonus in the form of a five- thousand-dollar sale to
for the magazine serialization of
Death in the Afternoon,
things were going well between him and his second wife, Pauline, and he was intrigued with his current project in
To Have and Have Not,
where he intended to bring fictive life to all the Key West lore and legend that he had accumulated since moving to the island city in 1928.

Not a bad moment, then, not by any stretch of the imagination: the end of a good day’s effort, a drink in hand, a breezy porch to lounge upon for a glance at the day’s events . . . until everything suddenly changed.

! was the banner headline Hemingway found in front of him, and, just below, the details of a hurricane feared to be coming Key West’s way.

In those days, weather forecasting was primitive, by modern standards. The storm, which had formed off the coast of Africa sometime during the last week of August, had moved across the Atlantic, undetected by the likes of modern-day satellite eyes or storm-chasing converted bomber planes, and now it was zeroing in on the United States.

Ships steaming southward to Havana were the first to encounter the disturbance, then a minimal hurricane with winds hovering in the seventy-five-miles-per-hour range. The reports were forwarded by telegraph back to Miami, where, in good time, newspapers had passed along the news. Though there were no computer tracking models to consult, in the Keys the average landmass lay lower than the top of a small child’s head above sea level, and any fool—much less Ernest Hemingway—knew enough to get ready for trouble.

The papers reported the location of the storm at press time as just east of Long Island, in the Bahamas, some four hundred miles east of Key West. Hemingway finished his drink, put his paper down, and went into the house to dig out his storm charts, one of which detailed the dates and tracking of the forty hurricanes that had, since 1900, approached Florida during the month of September.

Given the reported rate of speed for the current storm (the quaint practice of naming hurricanes was not adopted by the U.S. Weather Bureau until 1953), Hemingway calculated—without the aid of television newsmen or late-breaking advisories—that he had until noon on Labor Day Monday before the worst might hit.

Hemingway’s first concern was his beloved boat,
a forty-foot powered fishing yacht he’d had built to order in a New York shipyard hardly a year before. His game-fishing forays about the northern Caribbean with Pauline and fellow writer John Dos Passos and Key West barkeep “Sloppy Joe” Russell and famed bullfighter Sidney Franklin and so many others were already the stuff of local legend, and Hemingway was prone to discuss the boat with others in a way that sometimes made casual acquaintances think he was referring to a lover.

As anyone who has tried to secure a boat in the face of an advancing hurricane can attest, however, the process is a tedious and frustrating one, complicated by a steady escalation of panic among other owners, many of whom may not have visited their craft in months. And Hemingway, despite his notoriety, found himself no exception. In a piece he wrote for
The Masses,
a left-leaning publication of the day, he shares a vivid picture of what he was up against.

Sunday you spend making the boat as safe as you can. When they refuse to haul her out on the ways because there are too many boats ahead, you buy $52 of new heavy hawser and shift her to what seems the safest part of the submarine base and tie her up there.

With the boat attended to as best he could, Hemingway spent the rest of Sunday evening and the following morning feverishly moving lawn furniture, carrying in plants, and shooing the ever-present horde of cats inside his house, then nailing makeshift wooden shutters over all the windows. By five in the afternoon the storm had not materialized, but the double red and black flags that signified an impending hurricane were snapping over the Key West harbor in a heavy northeast wind. The barometer was falling precipitously, and the streets all over the town resounded with the crack of hammers driving nails into shutters, which nervous owners only hoped would hold.

With nothing more to do at home, Hemingway left Pauline and returned to the Navy yard where he’d tied up

You go down to the boat and wrap the lines with canvas where they will chafe when the surge starts, and believe that she has a good chance to ride it out . . . provided no other boat smashes into you and sinks you. There is a booze boat seized by the Coast Guard tied next to you and you notice her stern lines are only tied to ringbolts in the stern, and you start bellyaching about that. . . .

Hemingway was enough of a sailor to know that lines attached to a few bolts drilled into the deck of a poorly maintained boat could never withstand the pressure exerted by the winds of a hurricane, but his complaints had little effect on an already overburdened staff. The harbormaster simply shrugged and told him he had permission to sink the rumrunner if she broke free and threatened to ram

Just how Hemingway was supposed to manage such a feat in the midst of a hurricane was not made clear, but there was nothing else to be done at the basin. He gave one last baleful glance at the precariously tied-off rumrunner, then made his way back to the house on Whitehead Street, left with the very worst thing to do as a hurricane approaches: wait.

From the last advisory you figure we will not get it until midnight, and at ten o’clock you leave the Weather Bureau and go home to see if you can get two hours’ sleep before it starts, leaving the car in front of the house because you do not trust the rickety garage, putting the barometer and a flashlight by the bed for when the electric lights go. At midnight the wind is howling, the glass is 29.55 and dropping while you watch it, and rain is coming in sheets. You dress, find the car drowned out, make your way to the boat with a flashlight with branches falling and wires going down. The flashlight shorts in the rain, and the wind is now coming in heavy gusts from the northwest. . . . you have to crouch over to make headway against it. You figure if we get the hurricane . . . you will lose the boat and you never will have enough money to get another. You feel like hell.

Hemingway’s preparations, and his premonitions, were well founded, as it turns out. On Matecumbe Key, some eighty miles to the north and east of Key West, the full force of the storm had already begun to sweep ashore. Residents of Islamorada, the principal settlement on Matecumbe, stared in disbelief as their barometers plunged from a normal 29.92 down to 26.35 inches of mercury, the lowest reading ever recorded in U.S. history.

Local residents had endured fearsome tropical winds before, and had some idea of what to expect. But this was no ordinary storm, and the situation on Matecumbe at this particular time was especially dire.

As part of his New Deal, Franklin Roosevelt’s Federal Emergency Relief Administration had put 650 indigent World War I veterans to work on a highway building project near Islamorada, using a route that paralleled what was then the only link across the low-lying islands between Miami and Key West: 153 oceangoing miles of Florida East Coast Railway track, a daunting project completed in 1912 by Henry Morrison Flagler, and often referred to as “the Eighth Wonder of the World.”

The work camp for the new highway-building project was situated on Matecumbe Key; offices were nothing more than a few hastily constructed outbuildings; the workers, most brought in from Northern cities and lacking any notion of what horrors a hurricane might bring, were housed in flimsy tents.

And the storm, as if sensing the most vulnerable place to come ashore, had drifted slightly east of Key West. As the monster began to hammer the camps, panic became the order of the day. Winds were already gusting over 155 miles per hour, the contemporary threshold for a Category 5 superstorm. Such categories had not yet been developed in 1935, but as one former resident remarked, “we saw pretty quick this was going to be a son-of-a-bitch.”

Power was out and tents were shredding away like tissue, leaving men to cling to staves, mangrove roots, even train rails, to keep from being blown off into the rain-lashed darkness. One vet tied himself to a tree with his belt, but his reprieve was short-lived when the wind tore the tree up by its roots and carried it, and him, away.

Melton Jarrell, one of the camp workmen, described his ordeal in a story carried by the
Miami Herald
: “I made for the railroad and hung onto it. A heavy sea came along and washed it up and as it settled back down, it pinned my left leg under it. In horrible agony, I decided to cut my foot off but I couldn’t get to my penknife. After that, I passed out.”

At nearly the same time that Jarrell had been about to hack off his own foot with his pocketknife, a permanent Islamorada resident, Bernard Russell, then seventeen, had run for shelter in a lime-packing shed, along with his parents, three sisters, and an uncle and his five children. The Russells, whose patriarch, John Henry Russell, had emigrated to the Keys from the Bahamas in the middle of the nineteenth century, were part of an extended farming and fishing clan numbering more than sixty that populated Matecumbe and others of the Middle and Lower Keys.

“We were going to ride it out in the beach house, but my dad saw how it was going and changed his mind. We headed for the packing house, which was close to the railroad, and on higher ground,” Russell recalls.

The notion of “higher ground” is a relative one, given Keys topography. Most of the Keys are not true islands, but mere outcroppings of reef, calcified remains of sea life, which poke just above the level of the sea. Most of the formations are only a few hundred yards or less wide, enhanced here and there by dredging and other means of artificial fill. By most American standards there is little that resembles a rise, let alone a hill, not in the entire 220-mile stretch of the archipelago that runs from Biscayne Bay, off Miami, to the Dry Tortugas, seventy miles beyond Key West. The highest point in the inhabited keys, which range from Key Largo, fifty miles south of Miami, to Key West, another 110 miles south and west, is barely sixteen feet above sea level.

The “higher ground” Russell refers to, then, was that created by the mounding of a few feet of crushed limestone marl and gravel riprap to create the bed for the Florida East Coast Railway, a quarter of a century before the hurricane hit. From that vantage point it was possible to glance north and south and see ocean in either direction.

“We knew when the storm hit—at eight o’clock—because that’s when all the clocks and the watches stopped. That’s when the water started covering everything,” Russell says.

The wind was so strong by that point that the whole packing shed had begun to throb, each pulse growing stronger, like the chamber of a giant heart about to blow itself apart with its next beat. Russell’s father ordered the boy to stand against the door, which was vibrating like a tuning fork, ready to spring off its hinges. Russell continues:

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