Every state has a fascinating history, including the role of business and entrepreneurship.  The swamp that was much of Florida did not develop until the late 19th and early 20th centuries.  Two men, both named Henry, were perhaps the most important in that development.  They brought railroads to the state to make it accessible and built beautiful hotels to make it worth the trip.  Henry Flagler made the east coast of the state “happen.”  Henry Plant did the same with the west coast.  Their efforts led to the growth of the state which continues to make headlines today.  Here is a brief look at these two very different men and their accomplishments.  We start with the first born of the two, Henry Plant.

Henry Plant

Henry Bradley Plant was born in Connecticut in 1819.  Eager to go to work, he passed on the chance to attend Yale and instead became a “captain’s boy” and deck hand on a steamboat that ran from New Haven to New York.  As part of his duties, he handled express packages, improving their organization and handling.  By the 1840s, he had gone to work for one of the large express companies that worked with the railroads and steamship companies to expedite packages.  (The largest express company was American Express, whose founders later created another one, Wells, Fargo, when American Express decided not to expand to California.)

In 1853, he moved to Jacksonville, Florida, recommended for his sickly wife’s health.  The trip took eight days.  Upon getting to know the then-tiny village, Plant became excited about the future of Florida.  They returned north, whereupon Plant was given responsibility for all the activities of the big Adams Express Company south of the Potomac and Ohio Rivers.  This was a major challenge, as the transportation network of the south was years behind that of the north.  When the Civil War approached, Adams Express worried about the future of its southern operations and sold them to Henry Plant.  He organized the Southern Express Company in 1861.

Southern Express was named the Confederacy’s agent for collecting tariffs and moving money.  Understandably in a difficult position given his Yankee heritage, Plant feigned illness and sailed to Bermuda, then Canada, and then France and Canada again before returning to New York. 

After the Civil War, he returned to the south to reclaim leadership of Southern Express.  But the railroad system was worse than ever, much of it destroyed in the war.  So Plant began buying up small southern railroads at foreclosure sales in the late 1870s.  Over the next twenty years, he developed and expanded a large transportation system, “the Plant System,” including fourteen railroads, 2,100 miles of track, steamship lines, and hotels.  His system opened up central Florida, allowing orange growers to ship their products north.  He proceeded to build down the southwest coast of the state.

Between 1887 and 1898, he built hotels from Sanford to Tampa to Fort Myers.  Two of the most beautiful were the Tampa Bay Hotel and the Belleview Biltmore near Clearwater, one of America’s largest wooden buildings.

Tampa Bay Hotel
Belleview Biltmore

Henry Plant worked his entire life and became one of the richest men in the south.  He died in 1899 at the age of seventy-nine.  Three years later, his system was absorbed by the Atlantic Coast Line Railroad, which ran from Richmond, Virginia to Jacksonville. 

Henry Flagler

Henry Morrison Flagler, eleven years younger than Henry Plant, was born in Hopewell, New York in 1830.  At the age of fourteen, Flagler moved to Ohio where his stepbrother Stephen Harkness lived.  After working in a retail store and a grain business owned by a Harkness relative, in 1862 Flagler co-founded a salt mining company in Michigan, but that business failed.

Returning to the grain business in Bellevue, Ohio, he got to know Clevelander John D. Rockefeller, who was an agent for another salt company owned by the Harkness family.  By the mid-1860s, Rockefeller had left the grain business to enter Cleveland’s emerging oil refining industry, which used the newly discovered petroleum found in nearby parts of Pennsylvania.   In 1867, Rockefeller asked Flagler’s stepbrother Stephen Harkness to invest $100,000 in Rockefeller’s new oil business.  Harkness agreed, on the condition that Rockefeller hire Henry Flagler to watch over Harkness’s investment.  

It will come as no surprise that Rockefeller and his partners made a success of the business, Standard Oil, which continues today in numerous offspring including ExxonMobil and Chevron.  Henry Flagler was perhaps the most important person in the company after Rockefeller himself.  When John D. Rockefeller was asked if the Standard Oil company was the result of his thinking, he answered, “No, sir. I wish I had the brains to think of it. It was Henry M. Flagler.”  The story of Standard Oil, John Rockefeller, and his many partners is well-told in dozens of books and other sources.    

In 1877, Henry Flagler moved to New York City, eight years before Standard Oil relocated from Cleveland to the Big Apple.  While he continued to serve on the Standard Oil board of directors, a very, very wealthy Flagler retired from active management in 1882.

Meanwhile, he, like Henry Plant, became enthusiastic about the future of Florida.  Also like Plant, his first trip was to Jacksonville to improve his wife’s health.  When she died, Flagler married her caregiver.  After the wedding, they traveled to nearby historic St. Augustine, but Flagler found the transportation and hotel infrastructure lacking.  Between 1885 and 1887, he built the 540-room Ponce de Leon hotel there.

Ponce de Leon

Looking south down the east coast of Florida, Flagler began to envision an “American Riviera.”  He gradually acquired and built a railroad south from Jacksonville to Palm Beach, spending a fortune cutting through the swamp.  As he expanded his Florida East Coast Railway, he kept building hotels, including the 1,100-room Royal Poinciana and the Palm Beach Inn (later renamed The Breakers) in Palm Beach.

Royal Poinciana
The Breakers

In 1912, Flagler extended the Florida East Coast Railway to Key West by building an elaborate causeway system across the Florida Keys.  That part of the railroad was severely damaged in the hurricane of 1935 and was never rebuilt, instead replaced by a highway.

Henry Flagler died in 1913 at eighty-three, worth about $60 million ($1.6 billion in 2020 money).


Others followed the trail to Florida along the paths pioneered by Plant and Flagler, using their transportation systems to get there.  Until the creation of Amtrak, their two railroads hauled thousands of passengers from the northeast to Florida on beautiful passenger trains.

The Atlantic Coast Line, the 1902 successor to the Plant system, later merged with the parallel, competing Seaboard Air Line Railroad, which went through more evolutions before becoming part of the CSX system, one of the four giant American railroads today.  Trains headed down the east coast of Florida to Miami had to transfer to Flagler’s Florida East Coast, which also changed hands and since 2017 has been owned by copper mining and railroad company Grupo Mexico.  Both continue to be critical parts of Florida’s transportation infrastructure, hauling freight in and out of the state.

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