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

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Last Train to Paradise is acclaimed novelist Les Standiford’s fast-paced and gripping true account of the extraordinary construction and spectacular demise of the Key West Railroad—one of the greatest engineering feats ever undertaken, destroyed in one fell swoop by the Labor Day hurricane of 1935. Brilliant and driven entrepreneur Henry Flagler’s dream fulfilled, the Key West Railroad stood as a magnificent achievement for more than twenty-two years, heralded as “the Eighth Wonder of the World.” Standiford brings the full force and fury of 1935’s deadly “Storm of the Century” and its sweeping destruction of “the railroad that crossed an ocean” to terrifying life. Last Train to Paradise celebrates a crowning achievement of Gilded Age ambition in a sweeping tale of the powerful forces of human ingenuity colliding with the even greater forces of nature’s wrath.

282 pages, Paperback

First published September 1, 2002

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About the author

Les Standiford

40 books155 followers
Les Standiford is a historian and author and has since 1985 been the Director of the Florida International University Creative Writing Program. Standiford has been awarded the Frank O'Connor Award for Short Fiction, a Florida Individual Artist Fellowship in Fiction, and a National Endowment for the Arts Fellowship in Fiction, and belongs to the Associated Writing Programs, Mystery Writers of America, and the Writers Guild.

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Displaying 1 - 30 of 565 reviews
Profile Image for Brina.
1,238 reviews4 followers
February 11, 2020
Each winter my family spends winter break in Florida. The sparkling sea and sandy beaches, palm trees, and gorgeous weather makes it difficult for me to want to return home. This year while I was sitting poolside and enjoying my time in the warmth, I noticed that one of my goodreads friends had read a book about Florida business magnate Henry Flagler. Wanting to hold onto my time in the sunshine state for as long as I could, I decided to read about Flagler and his proposed railroad upon my return home.

Henry Flagler was born on January 2, 1830 in upstate New York. His family moved to Bellevue, Ohio outside of Cleveland when Henry was about to enter high school. This move became a life changing event for young Flagler who even as a teenager maintained a strong business sense. When he finished college, he went to work with the Harkness Company, and this employment lead to a lifelong business relationship with one John D. Rockefeller. Rockefeller and Flagler walked to work together on a daily basis, throwing ideas back and forth. It was Flagler who had the foresight to shift the current business operations from timber to oil, and thus Standard Oil was born. Rockefeller admitted that Flagler was the brains behind the Standard Oil operation, and, even though Rockefeller went on to become the richest man in America, Flagler, through his shares in Standard Oil, amassed a fortune of his own. It is how Flagler chose to spend his millions that made him both the founder of south Florida and a fool to many people.

The gilded age was the age of railroads. When Flagler began to winter in both Jacksonville and St Augustine, Florida to assist the health of his second wife, he realized that there was no railroad linking St Augustine with the St John’s River area. This kernel of an idea lead to the formation of the Florida East Coast Railroad. As Floridians living in the wilderness and northerners began to take the train to the coast, Flagler began the construction of luxurious hotels as well as a mansion for himself. Each summer he would return to his estate Satan’s Toe at Mamaroneck, New York but would eagerly return to Florida each winter. With each passing year, Flagler would relocate further south, constructing railroad ties and building hotels and estates along the way. His Florida East Coast Railroad lead to the formation of Palm Beach and it’s iconic Breakers Hotel and the birth of a southern Florida vacation for the wealthy set. The Breakers has been persevered today as the Henry M Flagler Museum as his role in the building of modern Florida has not been diminished over time. Yet, Flagler did not stop in Palm Beach; he sought to build his railroad south to a sleepy village, which he would rename Miami, in homage to the native Americans who once populated the area.

Miami today is the gateway to Latin American, and South Beach rivals Malibu on the west coast for its glitz and celebrities who flock there. There would have been no Miami as we know it had Henry Flagler stopped in Palm Beach, and the Florida East Coast Railroad continued south. Flagler had no designs to stop. His vision spread to the terminus of the United States: the Florida Keys. In the early 1900s, President Theodore Roosevelt had successfully defeated Spain in Cuba two years earlier. The United States has no rival for power in the Western Hemisphere and there was talk of construction a canal in Panama, which would be completed in 1914. Key West is located three hundred miles closer to Panama than Miami. Flagler believed that the isle could become a key deep water port for international trade and a jumping off point to Cuba and Central and South America. So he did the only logical thing that he knew: he had the Florida East Coast Railroad begin construction of an overland and sea line that would span the keys all the way to Key West. The project would cost him millions of his fortune yet could provide New Yorkers passage directly to Cuba. The idea seemed brilliant; naysayers called the railroad Flagler’s Folly.

Les Standiford is a Florida native and has written many books on the state. This fast moving account focuses primarily on the construction of the Florida Keys extension of the Florida East Coast Railroad. At times, he detailed the engineering behind the feat which was ingenious but also tedious to read about. Just the construction of the Bahia Honda or Seven Mile Bridge linking Long Key to the Lower Keys was a feat in itself. Standiford contrasted the speed it took to build the railroad with the time left in Flagler’s life and how crews worked around the calendar, even in perilous conditions in order to finish the project during Flagler’s lifetime. One thing Flagler did not foresee was hurricanes, which damaged the railroad nearly beyond repair multiple times. Hurricanes struck the Keys in 1906, 1907, 1909, and 1910, almost ruining the project; yet, Flagler had spent over $20 million of his fortune to see the project come to fruition, and he was determined to see it through. Many believe it was the only thing keeping him alive at the time. So engineers and railroad workers pressed on, often at a cost to their lives, in order for Flagler to witness the completion of his railroad.

The 1935 hurricane destroyed the railroad and much of the Keys, and today all that is left of the trestles is the overland bridge, which spans the highway which runs the length of the east coast from Maine to Key West. Key West never became the shipping center that Henry Flagler envisioned but has remained a tourist destination for northerners starved for sunshine as it is the closest point in the United States to the tropics. Flagler is known as the founder of modern Florida for his role in building up cities up and down the coast. I am grateful for him because I do travel to Florida each winter, escaping the cold. Next winter I may have to forgo the sun for a few hours and visit the Flagler Museum. His life rivals that of his fellow robber barons of the gilded age, yet he is usually overlooked outside of the Sunshine State.

4 stars
Profile Image for Jennifer.
88 reviews1 follower
September 29, 2011
This audiobook gets my biggest compliment: I will be listening to it again! It's full of interesting facts about Florida history that go far beyond the railroad (including lots of information about Hurricane Andrew). Since I live in the Keys, I especially enjoyed hearing about life here when the islands were only accessible by boat. The endearing tales of Flagler's ups and downs throughout his career and three marriages will keep your attention, as well as seldom-heard histories of others involved with the railroad such as Cornellian William Krome. If considering a book or audiobook, definitely go for the audiobook; the wonderful narrator is like your grandfather telling you a thrilling bedtime story. On that note, though, I would caution that this is not a book for children. The descriptions of deaths in the hurricanes are quite graphic.
Profile Image for Lorna.
1,003 reviews720 followers
April 29, 2020
Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of a Railroad that Crossed an Ocean was a captivating book by Les Standiford of robber baron Henry Flagler, partner with John D Rockefeller in the founding of Standard Oil. Later when he discovered Florida, the historic and lovely St. Augustine and the beautiful St. John's River, he was captivated and built his first hotel. That hotel was followed by others, including The Breakers in Palm Beach. Through his business investments and the time that he and his family spent in Florida, he became interested in developing a railroad throughout the state, first primarily to his hotel resorts and home but then later became very interested in the Florida Keys. Against all obstacles Flagler relentlessly pursued his dream of building a railway system to land's end, the southernmost tip of the United States in Key West, Florida. Because of the recent election of Theodore Roosevelt and his determination to complete the Panama Canal, Flagler was determined to build his Florida Overseas Railroad from Miami over the chain of islands known as the Florida Keys. Although, he did prevail amidst a lot of setbacks and adversity, ultimately his railroad succumbed to a fatal blow of nature when Category 5 hurricane winds wiped out large portions of the railroad and never to be restored. Having spent a lot of time in southeast Florida, I can say that the Florida Keys are one of our favorite destinations, as you travel by car on the Overseas Highway, mesmerized by the sparkling sunlit waters on either side of the highway and find yourself happily immersed in this magical paradise. But there are many reminders, particularly the spectacular overseas bridges with railroad tracks to remind one what was before, now enticing bicycle and hiking paths. Flagler was a true visionary.

"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."

"This much is certain: Most contemporary travelers who travel the 128.4 miles of U.S. 1 that now stitch the Florida Keys, from Homestead at the tip of the U.S. mainland to Key West at the very end of the line, find it one of the most remarkable stretches of highway in the country. . . . This piece of highway also offers a certain definitiveness, a very inescapable destination: Key West sits literally at the end of the American road, and for most of the twentieth century the "Southernmost City" has sung a siren's song to tourists and travelers, literati and glitterati, grifters and drifters and modern-day pirates alike."

"In a sense, the highway is what remains of one of the last great gasps of the era of Manifest Destiny and an undertaking that marked the true closing of an American Frontier."
Profile Image for Nan.
58 reviews3 followers
February 27, 2012
If you're going to read one book about the building -- and destruction, less than three decades later -- of the Overseas Railway, this is the book to read. January 2012 will be the Centennial of the completion of the railroad, which transformed the Florida Keys from an isolated island chain into an artificial peninsula, an extension of South Florida. Only a determined and extraordinarily wealthy man like Henry Flagler -- one of the original partners in Standard Oil -- could have seen the project through the logistical nightmares of its construction. Several books have been written about the project; this is by far the most readable (and it will be featured in spring 2012 in the Key West Library's One Island One Book program -- including an online readalong for folks who are out of town -- check www.oneislandonebook.blogspot.com for details).
Profile Image for Brenda.
217 reviews43 followers
February 11, 2022
I live in Florida although I'm not a Florida native so I thought this would be a good book to read to get some history of Florida. I've been to Mr. Flagler's mansion in Palm Beach and I see how many streets and institutions are named after him but I knew very little about the man. And now I do. Having lived in Key Largo for a bit helped me to visualize the landscape that was being described in the book. And if you've ever driven to Key West, you know what an undertaking it would be to build a railroad that would reach there. And if you've experienced hurricanes (I have...) you would understand the folly of building a railroad during hurricane season.

But Mr. Flagler was a unique man and I'm grateful for what he attempted to do. I felt anxiety and awe at the same time when discovering all that the man accomplished. If you want to know more about Mr. Flagler, Florida, and the Keys; I would recommend reading this.
Profile Image for Literary Chic.
220 reviews3 followers
May 10, 2017
Fascinating! This was my audiobook recently. It focused mainly on Flager's later life (post Standard Oil.) He split from Rockefeller and spent his senior years building Florida. After reading this book, I'm amazed at how basically one mans work developed the entire eastern coast of Florida....and he did this during his "retirement."

***There was a nice Louisville tie-in. Flager's widow (Mary Lily) was 37 years his junior and remarried after Flager's death. She married Robert Worth Bingham of Louisville in 1916 and died less than a year later leaving a highly contested will and $5MM to her new husband. The legacy allowed Bingham to buy The Courier-Journal, Louisville's newspaper. The Bingham family was extremely influential in my hometown until the mid 80's when the siblings fought so much that the family sold all their businesses including the paper.
Profile Image for Gerry.
Author 43 books118 followers
December 4, 2018
As a multi-millionaire and a major shareholder in Standard Oil, one could be forgiven for thinking that the aging Henry Flagler need do nothing else during the remainder of his life. But that would not have suited this remarkable, all-action man.

He had a vision of developing Florida and then providing a railroad across the Florida Keys to facilitate communications with Cuba and provide quicker access for the Keys, which previously were reached by ship. He was successful in providing hotels and other facilities on the mainland and putting Florida on the map as a holiday resort but when it came to the railroad, financiers thought it was utter madness. 'Unthinkable', they said and then the engineers stated, 'Impossible'. But Flagler was undeterred and author Les Standiford charts the events that led to his eventual success in providing the railway line from the mainland through to the final of the Keys, Key West.

But it was not all plain sailing, or plain railroading, for there were seemingly insurmountable problems in building over the Atlantic but Flagler and his team overcame them all. What he could not overcome, however, was the weather and hurricanes in 1906 and 1908 destroyed much of his work that all had to be carried out again. It was, and the line went through albeit attracting the moniker 'Flagler's Folly'.

Flagler, much-married, travelled down on the first train from Miami to Key West on 22 January 1912 but he saw his railroad operate for only just over 12 months for he died on 20 May 1913. His railroad survived him for only 22 years for another hurricane, the most powerful recorded in America, struck on 2 September 1935 and the devastation was massive, so much so that much of the line was destroyed and never replaced.

The author charts the complete, extraordinary story in remarkable fashion while also capturing Henry Flagler's character in a rousing way. The book reads like a thriller and will keep many a reader engrossed as the tale of perhaps one of America's greatest engineering feats develops.
32 reviews
August 6, 2013
Wow! Reading this book I was perpetually inspired by the resolve of Henry Flagler and the engineers he employed. I wish engineers were routinely so daring and visionary now! At no point did I find the book to drag. Rather, it just seemed to move more quickly in some places than others. Some of the descriptions of events leading to the development of the project as well as it's eventual destruction are done so well that I could just see it despite having never been to the Florida Keys. Great read!
Profile Image for Tim Martin.
856 reviews52 followers
July 1, 2017
This was a gripping, very fast-reading account of one of the greatest engineering challenges in American history, the construction of the Key West Extension of the Florida East Coast Railway. Also known as the Overseas Railroad and for a time derisively as Flagler’s Folly, it was an ambitious project designed to link Key West, Florida with the mainland, some 128 miles away. This book chronicles the initial ideas behind building the railroad, its construction (begun in 1905), its operation (from 1912 to 1935), what happened to the tracks and the railway after 1935, the impact the railway’s construction and operation had on the state of Florida and on Key West, and the life and times of the driving force behind it, Henry Flagler (who just barely lived to see the railroad’s completion, passing away in 1913).

The author’s skill at crafting a narrative certainly showed in the initial chapter, as it was one of the most gripping non-fiction pieces of writing I have ever read. It detailed the events leading up to and at the height of the apocalyptic Labor Day weekend hurricane of 1935, the author skillfully and suspensefullly switching between various viewpoints (Ernest Hemingway in Key West, Melton Jarrell, one of the workmen on Matecumbe Key, part of a Federal Emergency Relief Administration or FERA work project that put some 600 World War I veterans to work constructing a highway building project, sadly living in flimsy tents and other structures, Bernard Russell and his family, a permanent Islamorada resident, and of J.J. Haycraft, engineer in charge of Old 447, a rescue train dispatched from Miami just before the hurricane to evacuate the workmen and residents). Blending first-hand accounts from the people involved and a well-written narrative, the author created a page turning epic of people trying to contend with a monstrous hurricane, boasting 200 mph winds (“fewer than 3 percent of tornadoes ever generate winds of more than 206 miles per hour” let alone that many hurricanes), huge storm surges (a problem in a chain of islands where the highest elevation is about 16 feet above sea level and much of it around 7 feet, with even the largest of the islands only a few hundred yards wide), and a nearly twenty foot tidal wave, which closed the chapter as it closed in on Old 447; “[a] dark wall that was rushing towards them, a swath of blackness and evil that seemed to swallow the dim illumination of the locomotive’s headlamps…it stretched across the horizon from end to end like the sweep of doom itself…A tidal wave. The worst that had ever struck American shores. Then and now.”

Gripping stuff, and fair warning, the author doesn’t return to readers to what happened next until chapter 23 (and it wasn’t nice, as quite a few people perished, anywhere from the official Red Cross death toll of 408 to possibly as much as 600, a problem exacerbated by “an uncertain Keys census and the a general laxity in FERA’s record keeping,” with sadly 63 members of the Russell family perishing and only 11 “lived to remember its horrors”).

The book was a great blend of the clashes of personalities in building the railroad, the many engineering challenges, the zeitgeist of the time that lead to its creation, and the personal struggles of Flagler in creating something many told him simply couldn’t be done (including marital, political, and economic issues, as Flagler had to contend with everything from failing health to a wife that had to be committed to challenges from the increasing regulations that were ending the Gilded Age economic era and distracting him from his beloved railroad). Perhaps most of all what stood out were the harrowing tales of survival as people survived accidents and not one, not two, but four hurricanes during the railroad’s all too brief history (the 1906 hurricane, which struck the Upper Keys, right where construction was at the time, the 1909 hurricane, which hit the Middle Keys, again, right where construction was at the time, the 1910 hurricane that hit the Lower Keys, again, pretty much again where construction was, and the Overseas Railroad-ending 1935 hurricane). In a far from dry section, the author also detailed the operational challenges faced by the Overseas Railroad (ranging from the economics of what did - or did not – arrive to make use of the railway, challenges faced at the Key West end in terms of efforts at expansion, and various other challenges, such as an investigation in 1927 whether or not the Overseas Railroad was diverting the Gulf Stream and plunging Europe into colder weather).

The entire history of the endeavor really lent itself to page-turning non-fiction writing, as there were so many factors that worked to give a sense of urgency. Sometimes it was the efforts to save people from the devastating hurricanes, while other times it was the realities of what drove people to take such risks in the first place, as the engineers and planners during each hurricane season faced the daunting prospects of working in hurricane season, all in a never-ending drive to finish the railway line before Flagler passed away.

There was so much I didn’t know before reading this book. I had heard of Flagler before reading this, but only in connection with the railroad, not his association with Rockefeller and Standard Oil (at one time the largest corporation in the world). I had no idea that at the time of the start of the railroad not only was there essentially no Miami but that Key West was the largest city in Florida and had been so for more than fifty years (as it had a well-developed economy based on cigar-making, fishing, sponge diving, and shipbuilding among other things, making it the thirteenth busiest port in the nation). Prior to the construction of the railroad, there often wasn’t much of a positive perception of the other Keys, with one person writing they were “worthless, chaotic fragments of coral reef, limestone, and mangrove swamps…and have been aptly called the sweepings and debris which the Creator hurled out to sea after he had finished shaping Florida.” I learned about Flagler’s involvement in building hotels and resorts up and down the line (and prior to construction of the Overseas Railroad, in peninsular Florida) and his commitment to not contract out the construction of the railroad, an expensive endeavor (the 742 mile California link of the Union Pacific Railroad, joined by the famed “golden spike” in 1869 at Promontory Point, Utah, cost $23 million, while the Overseas Railroad cost well beyond $27 million). Also Flagler’s commitment to the people of Florida – “I feel that these people are wards of mine and have a special claim upon me” – as he not only helped improve living conditions for residents of Florida, expand their economy tremendously, gave out disaster relief, but worked hard to provide good and safe living conditions to those building the railroad (with each successive hurricane forcing them to learn new lessons on how to prevent death and damage to the men and equipment) as Flagler built and maintain hospitals and after the first disastrous hurricane, stormproof shelters (though despite all his care of his workers and of nearby residents, there was a serious 1907 investigation in New York over whether or not Flagler and the FEC used slave labor).

The engineering challenges of the railroad’s construction aren’t lost in the midst of the human story, as there is a great deal of coverage of this. The reader learns for instance that at one point “three tugs, eight Mississippi River sternwheelers, more than two dozen motor launches ranging from five to fifty horsepower, a dozen dredges,…and a specialized catamaran for building concrete” forms were in use in construction. The author provided great coverage of Chief Engineer Joseph C. Meredith, whose innovations and techniques in reinforced concrete were key to the railroad’s completion. Another individual that gets a lot of coverage in terms of the actual construction of the railway was Joseph Parrott, Flagler’s general manager (who among other things at one point “chartered every American steamship available for hire on the East Coast to haul hundreds of thousands of tons of coal, steel, lumber, machine tools, food, and medical supplies” and upon reaching Key West and reporting to Flagler “There is no more dry land in Key West,” was told by Flagler “Then make some” and did).

Well written history, it was a great read. It had a number of photos, maps, and an impressively detailed bibliography.
Profile Image for Joseph Pitard.
50 reviews
February 23, 2023
“I prefer to let what I have done speak for me”

Henry Flagler is a man who helped build America. Made millions of dollars of Standard Oil with John D. Rockefeller and decided build things. Flagler is responsible for building the infrastructure on the entire east side of Florida. He used nearly his whole net worth to fund the most ambitious project of the time.

I really enjoyed reading most of this book, but the beginning and the end did not seem to work well with the rest of the book. This isn’t a spoiler, but when Henry Flagler died, the author decided to just talk about Hurricanes and it is very uninteresting to me.
Profile Image for Joseph.
10 reviews1 follower
October 6, 2022
Excellent read and a great insight into Flagler’s significance to Florida.
Profile Image for Vicky Hunt.
959 reviews97 followers
October 6, 2024
Inventing Florida
Financier, Railroad Manager, & Engineer… Henry Flagler was all of these. A grandiose project or Flagler’s Folly; probably the Key West Railroad across the Florida Keys was both. But, that it had a huge impact on Florida's growth is unquestionable.

It could be said that the railroad was the catalyst for Atlanta becoming the transportation hub of the South as it is today. In similar manner, Henry Flagler has been called the man who invented Florida. Many of his day joked that the FLA on mail envelopes stood for Flagler, and it is true that his investment and building projects catapulted the state into a massive era of tourism. Definitely, Miami gained much from the construction of the railroad along the East Coast of Florida and its extension through the Florida keys. And, Flagler's innovation and entrepreneurial spirit is a good example of that which characterized the spirit of the "Gilded Age."

Last Train to Paradise does a good job of detailing the process of planning and construction of the Key West Railroad that connected the keys to the mainland. The book also gives a good deal of biographical information about Flagler's life work. He spent his early years amassing wealth through investment, but later turned his income to massive building projects. Though they diminished the wealth left to his heirs, and the Key West Railroad was destroyed within 3 decades by the devastating hurricane of 1935, the investment made huge dividends in Florida's economy to this day. And, it was the largest real estate purchase in history.

One of his best known investments was the Standard Oil Company, which he and Rockefeller built. The Key West Railroad is what Flagler is best remembered for today. Les Standiford covers the loss of life in the hurricane of 1935 in graphic manner. The book covers geography, culture, and other interesting info about the Florida Keys. I recommend this book for anyone interested in the growth of the South, or railroads in general. I read it as part of a theme list of books I've selected on trains that I'm reading along with my Journey around the World in 80 books. I'd planned to read Ghost Train Through the Andes before leaving South America, but that paperback was delayed in shipment, finally arrived only today, and here I'm already out into the Caribbean. :) Looks like I'll have to take a virtual side trip back ashore to catch the Ghost Train now before sailing back out to Puerto Rico.
Profile Image for Andie.
1,025 reviews8 followers
May 29, 2015
As Carl Hiaasem talks about in his comic thrillers, Florida has long been home to disreputable developers, business shysters and other unsavory characters who have raped the lush landscape of the state for fun and profit, and no one's name is more connected to Florida's notorious business practices than Henry Flager who not only built a hotel empire in Florida and almost single-handedly built Miami and Palm Beach, but also built an improbably railroads line from Miami to Key West.

Flagler who was John D. Rockefeller's partner in Standard Oil of Ohio (and also the author of that company's most notorious business practices) fell under the spell of Florida in the early years of the twentieth century and proceeded to make building a railroad line to Key West his life's obsession.

Long called "Flagler's Folly" he refused to let heat, disease or multiple hurricanes deter him from his dream of extending rail service from Miami to the southernmost edge of the United States. The railway came into existence after many years of effort, but Flagler's dreams of making Key West the country's major deep water port did not.And when in 1935 a devastating hurricane destroyed the railroad once and for all, all that was left of Flagler's dream were a few Ozymandias-like remnants of his efforts.

Today Florida's fragile environment is still under assault from rapacious developers who disregard the land in favor of quick profits. MAybe they should read this book and then think twice before starting the bulldozers on yet another dubious development.
Profile Image for Nan Williams.
1,680 reviews98 followers
September 10, 2020
This was a most interesting biography of Henry Flagler with the emphasis on his development of the state of Florida. Following the development with Rockefeller of Standard Oil, Flagler took a vacation to Jacksonville, Florida and then meandered on down the coast to St. Augustine. He saw the potential for development of a tourist mecca, but being a wise planner and a wise businessman, also saw the need for a train and other support features such as hotels.

For twenty five years Flagler invested his own fortune in developing the east coast of Florida and building the east Florida railway line. He built opulent homes and magnificent hotels all along the rail line from Jacksonville to Miami. He built Palm Beach, itself. After establishing Miami, he made a trip to Key West and saw the commercial potential in that southernmost point of the US. He made the decision to extend his railroad over 192 miles of tiny islands interspersed with a lot of ocean! Building a railroad over such terrain was quite an engineering feat, but also a feat continuously met with one obstacle after another. If it weren’t a labor problem, it would be a hurricane. During the 12 years it took to complete the extension, there were 3 major hurricanes in the keys.

The railroad was finished in 1912 in time for Flagler’s 82nd birthday. A year later he was dead.

Covered in this book was a lot of US history and a lot of historical characters (like Hemmingway). Flagler was born in 1830 and the book covered the period up to WWII.

Very enjoyable and highly recommended.
Profile Image for Bill Yarbrough.
225 reviews18 followers
July 5, 2018
Awesome book. Reading about such an event makes me remember similar events in my life, and how I can relate to something so real.
Profile Image for Charlie.
79 reviews2 followers
Read
December 31, 2022
not fair to rate a hate read. a capitalist’s pipe dream sponsored by convict labor and habitat destruction
Profile Image for Joe1207.
60 reviews5 followers
August 4, 2017
The first chapter hooked me, but then it steadily got worse. The second wasn't much better. I almost stopped reading, but the third chapter started to talk about Flagler, and after a few more pages I decided to stick it out. It was smooth sailing (yikes) until the last two chapters, which makes for a fitting parallel with the beginning, I guess.

Standiford is dramatic. He personifies weather like a Victorian. "And the storm, as if sensing the most vulnerable place to come ashore, had drifted slightly east of Key West." (7). Chapter 22 ends, “[Building a highway] was an intriguing question, of course, but it would never be answered. Before men could finally address the issue, nature decided the matter by herself.” (224). A couple pages later, this sentence ends a section: “But little had changed in the science of hurricane forecasting between 1910 and 1935, and without the monster staring you in the eye, it is hard to fathom the reality of impending doom.” (227).

https://www.youtube.com/watch?v=a1Y73...

Since he’s talking about hurricanes most of the time, it’s forgivable. But he does the same with people and events. The end of the first chapter, after the engineer of Flagler’s locomotive tries to escape the incoming tidal surge:

“A dark wall was rushing toward them, a swath of blackness and evil that seemed to swallow the dim illumination of the locomotive’s headlamps. Nearly twenty feet tall it was, and it stretched across the horizon from end to end like the sweep of doom itself.
A tidal wave. The worst that had ever struck American shores. Then and now.
‘Lord have mercy,’ J. J. Haycraft murmured, his hand going instinctively for the throttle. And everything was dark.”

https://www.youtube.com/watch?v=G44xT...

I didn’t think much about the whole tidal wave thing until the end of the book, when Standiford revisits Haycraft again via the 1935 issue of the Monthly Weather Review: “‘The track and crossties of the railroad were in one stretch washed off a concrete viaduct thirty feet above ordinary water level…’” (237).

I guess it was actually thirty feet.

I thought the whole thing sounded strange, so I googled “worst tidal wave to hit US.” The first result was a 1,720 ft. wave at Lituya Bay, Alaska in 1958. Hm. Then I realized it sounded off to me because tidal waves and tidal surges aren’t the same thing. Earthquakes and volcanos create the former, low pressure storms create the latter. It's a common mistake, but it really shouldn't be in here. I get the appeal though, because saying tidal wave sounds more…dramatic.

More on the people of this book. Here is Joseph C. Meredith, commander in chief of the railroad project:

“…‘who wouldn’t give a year of his life to have Mr. Flagler see the work completed!’
It was a statement that in Meredith’s case would prove to be prophetic. For, deep inside, this taciturn man bore a secret that he had divulged to no one, and which would one day have profound consequences for this undertaking.” (119).

We probably learned what the secret was, but idk.

About the man himself:

“No one will ever know just what thoughts ran through Flagler’s mind as he stood before the crowds that day, of course. So many years had passed between the undertaking of the project and its completion that some sense of anticlimax would have been inevitable.” (204).

Well at least you didn’t contradict yourself in the next line or anything.

Then there’s maybe my favorite part in the book, a short section about Mr. Bernard Russell and his battle with the “maelstrom”:

“Scientists still debate whether true tornadoes are spawned within the bands of the most powerful hurricanes. Bernard Russell can tell you that he has no such doubts. For a whirling vortex had snatched him and his sister and her baby off the ground as if they were twigs, and was now spinning them about in an ever-expanding circle.
Russell struggled, but he was up against a force stronger than the fiercest human intent.” (231).

The writing had the potential to be really good, but it consistently fell flat on its face. But what bothered me most was the exaggeration. Missing details and feelings are filled in where historic accounts don’t say anything, or when Standiford thinks they aren’t exciting enough. He makes serious situations unintentionally funny.

And then there's the insult to the reader's intelligence in the conclusion. Standiford finishes the story with a thorough explanation of Shelley's "Ozymandias," one of the most famous poems ever. Six of the poem’s last 14 lines were in the epigraph, which was plenty for the reader to get the gist of its meaning:

"Shelley’s poem ‘Ozymandias’ tells the fanciful tale of a wide-ranging traveler who encounters the shattered statue of a long-dead emperor tumbled to a barren desert landscape. The inscription on the blasted statue’s base commands the traveler, ‘Look on my Works, ye Mighty, and despair!’ though all there is to gaze upon are ‘lone and level sands.’ The enjoyment of the poem depends upon Shelley's implication that such grand dreams of the high and mighty are doomed to eventual ruin.
And so might a modern traveler find himself, halfway across the new Bahia Honda highway bridge, glancing off to eastward at the Stonehenge-like remains of that ancient railroad span still defying the Atlantic, perhaps thinking of Henry Flagler and, perhaps, tempted to buy into Shelley's argument.
But there is no stopping, not halfway across a busy highway bridge. And by the time the traveler reaches Key West, order is restored." (259).

So I guess Shelley was making an argument. And yeah, it’s probably not a good idea to stop on a one lane highway. What does he mean when he says order is restored? I wasn’t surprised to see Standiford teaches creative writing, and here's where my bias probably starts, because the book sounds a lot like the gut-feeling writing I encountered in college that glorifies emotional resonance over pragmatic clarity. It had all the facts and research, but it sidelined them under the assumption readers don’t want to sift through citations. It just wasn’t what I was looking for, unfortunately.

Another example of the author, out of the kindness of his heart, doing the thinking for us:

“There are no more men like Henry Flagler, and there are no more dreams like his. Today we have software titans, and their minions who seek to bridge gaps measured in millimicrons and nanoseconds. Such accomplishment may be dizzying in its own right…but that kind of bridge-building pales in comparison to those that Flagler built across the Florida Keys.” (258).

I suppose the enjoyment of the book depends upon Standiford’s implication that such grand dreams of the critical reader are doomed to eventual ruin.

Regardless, the acknowledgements really got to me:

“There are many other writers whose articles and books and stories have shed light on various aspects of the material herein. Because this book does not present itself as a work of traditional historical scholarship, however, and in order to lessen the burden on the general reader, I have attempted to make appropriate reference to these writers and works in the context of this story.” (262).

I guess I’m not a general reader since I expected citations. I wanted to see where Standiford got the info that the Keys hurricane produced the worst “tidal wave” ever recorded on American shores. And he embellishes the hurricane victims’ stories for pages at a time without citations. That really irked me. It felt exploitative. Like he rewrote another person’s account to better serve his purpose.

Again, it’s how you approach the book to begin with. I didn’t want all the added flair. I wanted to learn about Flagler. That’s why I enjoyed the middle 200 pages. But the beginning and ending really...doomed...it for me.

When I finished the book, I wanted to know what publication houses, journals or magazines would endorse a blockbuster-style “historical” narrative that manipulates the truth, patronizes readers, idolizes 19th century tycoons and attempts to dismiss Flagler’s controversial divorces and labor practices.

I turned the book over and the first blurb I saw:

“A fascinating and incredibly compelling account…I could not put it down.” –Donald Trump


There you have it. Everything makes sense now. Order is restored.

Profile Image for Sandy Nawrot.
1,075 reviews31 followers
March 25, 2020
I have a weird fascination with the Labor Day hurricane of 1935. I've read a number of books where this storm plays a part, but also because it's one of the most intense storms to hit us in terms of pressure. It destroyed the Keys. And these poor people never knew what was coming.

This storm was featured in the opening chapter of this book because in making landfall in the Keys, it completely destroyed Henry Flagler's 100 mile railway that was painstakingly built between Miami and Key West. Construction started in 1905 at the behest of oil tycoon Henry Flagler, who envisioned a deep-water port in Key West. He was told it was a crazy idea, that it wouldn't make a profit, but Flagler didn't listen. Just because an overseas railway had never been built didn't mean anything.
It was just a bigger challenge. The workers encountered mosquitoes that traveled in swarms, there were three separate hurricanes that stalled construction, took lives and damaged machinery, and it was expensive. It was finally completed in 1912, but never conjured the riches and Flagler dreamed of.

I find Florida history fascinating, and truly enjoyed learning about the building of this railway and about Henry Flagler himself. I've seen the remnants of the railway, and visited the memorial to the fallen railway workers in Islamorada. BUT (big but). The audio narration, in the hands of Del Roy, was horribly boring. His voice droned on and on to the point where it was very hard to concentrate. This book is best read in print.
Profile Image for Ann.
125 reviews9 followers
December 4, 2020
I read this as a follow up to a fictional book, The Last Train to Key West. I really enjoyed the history in the book, from Flagler’s relationship with the Rockefeller’s and Standard Oil, to the development of Florida, including Key West. I’m definitely interested in travel to Key West now to see the bridges and roads he was instrumental in building.
Profile Image for Jane Wiewora.
182 reviews
August 21, 2025
Read as part of the Read Together Palm Beach County selection for 2012
Profile Image for Amy.
402 reviews28 followers
November 25, 2022
I selected this one for our nature book club at the height of hurricane season. Standiford's writing style is very atmospheric and the story serves as a good reminder to be prepared and to never let your guard down during hurricane season. I also love this book for introducing me to the Bonus Army.
Profile Image for Sabrina.
87 reviews12 followers
June 26, 2019
Started with a fast paced chapter about the Hurricane of ‘35, but beyond that the pace slowed considerably. Almost like reading a textbook in my opinion. I was interested being invested in all things to do with the Florida Keys, but I believe a casual reader would most likely lose interest and abandon the book. Which would be a real shame - this is very well researched and included amazing insight into Flagler. Worth powering through. You will learn a lot.
Profile Image for Cece.
412 reviews40 followers
April 24, 2017
Picked up my copy while visiting my daughter who goes to school at Flagler College. While I have learned many things about Flagler, learning the railroad portion was quite fascinating. The storyline did drag a little at times which would be more of a 3 star rating, the sheer characterization of Flagler and learning all I did inspired me to give it a 4 star rating. Great and educational read.
Profile Image for Jeff.
Author 18 books38 followers
August 11, 2022
Great book about the railroad that was built all the way to Key West and the hurricane of Labor Day 1935 that ultimately destroyed it. As a book about a hurricane it is as good as Erik Larson's Isaac's Storm, but it also details the building of the Overseas Railway, as a fascinating story of an engineering feat.
Profile Image for Claudia.
1,288 reviews39 followers
November 13, 2020
When one considers the so-called Masters of Industry from post-Civil war into the Gilded Age of America, Henry Flagler is usually not one of the names commonly recalled. That is unfortunate because he made his fortune while a partner of John D. Rockefeller and made his fortune in Standard Oil.

The book actually starts with a train conductor trying to get into the Florida Keys to evacuate refugees from the incoming 1935 Hurricane. The train and most of its passengers didn't escape the fury of a storm that is even today considered one of the worst to ever hit the United States. But first, the author goes into Flagler's life, his attraction to Florida and eventually how he provided the East Coast of Florida with a railroad connecting it with the rest of the country. He is considered the father of not only the Florida East Coast Railway, but of the cities of Miami and Palm Beach.

The book just touches on those aspects along with the bridges he built to open the southern half of the state as well as the luxury hotels and surrounding estates - the so-called "American Riviera" - that lured the wealthy to the south during the cold northern months. But it was the Keys that caught his attention especially Key West - the southern-most deep-water port city - which was closest to the proposed Panama Canal.

So this is the story of a man who was willing to spend millions to connect Key West by railroad with the mainland of the state of Florida. He was certainly ahead of his time with the treatment of his thousands of workers - providing floating barracks (until the hurricane of 1906 showed how unstable they were) as well as wooden structures for his workers; plentiful and nourishing food and fresh water); reasonable wages as well as paying for workers from the north to take a train to their new employment site (several would get off the train elsewhere to work, never reimbursing the cost of the ticket); and medical care. In turn, they were working under horrible conditions - the swamp and marshland infested with poisonous snakes and infectious mosquitos. Fresh water had to be brought in by rail as the Keys did not have easily accessible water available at the time. that eventually led to small islands of ancient coral reefs.

After dealing with three separate hurricanes, the Florida Overseas railroad was completed in 1912 and Henry Flagler was able to travel via his own railcar along the entire route. Perhaps it was fortunate that he never saw the devastation that the 1935 storm did to the railroad and the islands. Rather than rebuild, the state of Florida authorized the construction of the Overseas Highway - U.S. Route 1 from Key West to Fort Kent, Maine. Many of the elegant bridges that Flagler had built for the railroad were used to cross the water and connect the individual islands were repurposed for the highway while others are left abandoned. The views of crystal blue ocean are part of the attraction even as drivers travel the highway from island to island.

It's a absorbing tale and it certainly provides insight into the opening up of the entire state of Florida as well as the origins of two of its major cities. Certainly makes me consider a road trip - but maybe not during hurricane season.

2020-227
Profile Image for Vicki Johnson.
37 reviews
March 3, 2019
I was especially interested in this book because I used to live in Daytona Beach and visited the city of Flagler occasionally. Henry Flagler was a very interesting (and rich) man. Unfortunately, his dream of the uses of a railroad to the Florida Keys was never realized.

The most interesting part of this book was the illustration of hurricane prediction technology in those days. They didn't have satellite prediction or hurricane hunters. The other very interesting part was how many times they rebuilt parts of the railroad after hurricanes came through. Each time, the railroad got stronger. But the final hurricane was more than anything could withstand.

I was amazed how many people don't realize that there used to be a railroad to the Florida Keys. I sure didn't before I read the book.

I most enjoyed the people stories in the book. The opening stories of Ernest Hemingway going to tie up his boat and the railroad engineer deciding to back the train down the track (while going to try to rescue people) so he could drive forward returning to Miami was fascinating.

The descriptions of the land and landmarks along the way through the keys was enlightening but didn't capture my interest as much as the people stories.
206 reviews1 follower
April 26, 2022
My last pre-pandemic vacation was to St. Augustine, FL which was essentially put on the map as a resort area by Henry Flagler, the virtually unknown partner of John D. Rockefeller of Standard Oil fame. Flagler's second career was to develop the east coast of Florida into the American Riviera. He was instrumental in building up Daytona Beach, Palm Beach and even Miami. Decades ago I was on a trip to Key West and heard the story of the railroad line that was blown away by a hurricane. Turns out Flagler built that railroad line too and hence this interesting book. The construction details and descriptions were at times hard for me to completely comprehend but the audacity and scope of the engineering accomplishment took my breath away. The author's first chapter describing the dreadful hours just before the horrific 1935 hurricane hit the Keys makes for absoluting thrilling reading.
Profile Image for Lyn Mahler.
319 reviews1 follower
October 25, 2020
This was fascinating history of Henry Flagler and his development of the east coast of Florida, running a railroad and a string of resorts from Jacksonville to Miami. His greatest challenge (some said his folly) was a rail all the way into Key West.It took many years, hundreds died, tons of obstacles, four hurricanes and most of his great fortune but he rode his own rails just before he died at the age of 83.

Staniford’s account of the 1935 Labor Day hurricane with its 200mph winds that flattened the Middle Keys, killed 600 people and ended “Flagler’s Folly” was hair raising! The fact that I read it as I traveled the bridges of the Keys myself at the time made it more so. Thank God for Flagler’s vision and his fortune that paved the way for so many to enjoy the paradise of the Florida Keys.
Profile Image for Chris Pitts.
29 reviews
November 22, 2020
I recently visited the Keys and was astonished to see the remains of a railroad spanning the ocean. I’m no engineer or architect but I could tell this was an amazing feat.

Lee Standiford does a terrific job explaining the person, motive, and process behind the Key West Railroad. It isn’t a biography of Henry Flagler; it stays true to its title and describes the rise and fall of the railroad.

The account leaves a sense of romanticism of a time long passed. When men sought to subdue the earth through incredible effort, resource, and ingenuity. It also captures the reality of living in a creation that often thwarts its would-be subduers.
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