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

End of the Line

Key West

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 tall, 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 new-found 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 administrator had published a pamphlet intended to boost tourism, listing Hemingway's home as 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 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 Scribner's 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.

Storm warning! 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 mile-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, Pilar, 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 hoard 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 Pilar:

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 Pilar.

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.