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“I would’ve been a rich man if it hadn’t been for Florida.” — Henry Flagler
Congratulations! You’ve founded the most successful company in the history of industry, and you’re rich beyond imagination. What do you do now? Do you do something traditional, like your partner, John D. Rockefeller, and reinvest your capital to secure an empire for your family? Or do you do something bold, something creative? How about developing a new hotel? Sounds great! Even better: you could build two of them, among the finest ever been built — the Ponce de León in St. Augustine, and the Royal Poinciana in Palm Beach. You can call your friend Thomas Edison, who’s recently harnessed residential electricity, and have him install light fixtures so new and so foreign to your guests that they refuse to flip the switches themselves because they’re terrified of being electrocuted. Marvelous! Splendid! But now you find that even this doesn’t do it. No, not quite. Your ambition is insatiable. You direct your attention to the state at large, to its pristine Eastern coastline, stretching 350 miles from Jacksonville to the end of the mainland, where an unnamed town exists as just a speck on a map — a place populated by fewer than 500 people. This place is great, you think. Why not share its splendor with the masses? Why not make it so that anyone with the money can traverse the sunny coast by rail? This could be the next great American frontier! This could be the country’s greatest tourist attraction! New Yorkers and Ohioans (like yourself) could come down in the winter months to rest their heels in the sand, to fish in the daytime and wait out the snow. And as a businessman — or at least that’s what you call yourself — you think of the return on investment. You think of pineapples shipped north from the perpetual warm weather. You think of oranges and sugar. Perfect! You form another company, the Florida East Coast Railway. You do what you set out to do. By 1896, a train leaving Jackonsville in the morning can arrive at the foot of Biscayne Bay that night. The town starts booming, so much so that its grateful settlers offer to name it after you. “Flagler,” you think, has a nice ring to it, but you’re a modest man — or so you tell yourself — and so you ask that they keep the place’s Native title of “Mayaimi,” or “Big Water,” inspired by the state’s great inland sea, Lake Okeechobee, located 80 miles to the north. It’s all falling into place now. It’s gelling together, except again you’re bored. You need excitement. Come on, now! You’re the second wealthiest man on the planet. You are quickly becoming the most significant person to ever set foot in Florida: four years ago, you persuaded the state’s legislature to alter their constitution, to make “incurable insanity” into acceptable grounds for divorce. You did this because, at 61 years old, you’ve fallen in love with a 23 year old and you need to get out of your second marriage. (The law is repealed immediately after you go through with it.) So you get back to scheming and again your gaze turns southward. This time, you notice the state’s busiest and most populous city, which also happens to be its southernmost: Key West. This, you think, is your chance to leave a real legacy, to reshape not only the state you’ve adopted as your own, but also the nation itself. By extending your railway 128 miles south from its current terminus in Miami, you’ll be able to harness the potential of the nation’s 13th-busiest shipping port. A couple problems, is all. One, how the Hell do you build a railroad over the ocean? The islands between Key West and Miami are faintly islands at all; they’re limestone and coral-encrusted speed bumps for waves. Their highest point is 16 feet above sea level, but the majority sits between three and four. Miles of open water span between each one, so you’re going to have to hopscotch your way down to the Conch Republic. Two, the proposed route will cost more than the 742-mile California installment of the Union Pacific Railroad. Three, it’s hurricane season. Four, you’re getting pretty old. No matter, you think. We’ve done it before; we’ll do it again. But how, exactly? For that, you’ll need to read Les Standiford’s Last Train to Paradise, the best book I’ve read all year.
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