Henry Flagler

Introduction

Today, when you ask someone if they know about Henry Flagler, they are likely to answer with a shake of their head and a shrug. If you ask the same question in Florida, most people will have known someone who lives on Flagler Blvd., in Flagler County, or down the road from the Flagler Museum. Generally, we are not often able to share specifics about the man himself. 

We Floridians have a very specific image of Henry Flagler in our minds: he is an old man with bright eyes cast in bronze. Stately and serious, genteel and generous — some have even referred to him as "Uncle Henry." 

However, this kindly nickname does not do justice to the full story of Flagler, who was nearly fifty years old when he first set foot in Florida in 1878.

Early Life

Henry Morrison Flagler was born in Hopewell, New York on January 2nd, 1830 to Isaac Flagler and Elizabeth Caldwell Harkness Flagler. 

Henry's birth heralded the beginning of a decade — and perhaps a new start for his family. He was the baby of the household, being born several years after the youngest of his siblings. Both of Henry's parents had been married previously. So, Henry was the youngest of a large mixed family. His half-sisters Mary Esther (16 y/o in 1830), Jane Augusta (14), and Caroline (3.5) were the daughters of his father's first two wives. Finally, Dan Harkness (7 — perhaps Henry's favorite sibling), was Henry's mother's son from her first husband. When he was a toddler, his two older half-sisters moved to New York to live with family, and Caroline ('Carrie') and Dan were Henry's constant companions. The family moved as was necessary for Isaac's job, having lived in Virginia and Ohio during Henry's childhood. Not much more is known about Henry Flagler's early life. 

After finishing the eighth grade at fourteen, Henry followed his half-brother Dan to Ohio. There, they were both given work by Lamon Harkness, who was the brother of Dan's late father. Together, the boys worked in the Harkness store for several years, where Henry eventually became a part of their sales staff. It was during these early years of employment that young Henry Flagler cut his teeth in business — one step closer to the shark he would become.

After finishing the eighth grade at fourteen, Henry followed his half-brother Dan to Ohio. There, they were both given work by Lamon Harkness, who was the brother of Dan's late father. Together, the boys worked in the Harkness store for several years, where Henry eventually became a part of their sales staff. It was during these early years of employment that young Henry Flagler cut his teeth in business — one step closer to the shark he would become. 

First Marriage, First Businesses 

By 1852, Henry had saved enough money to become the one-third-owner of the Harkness & Company alongside his half-brother Dan and Dan's uncle Lamon. Together, the three set their sights on opening a distillery that would serve nearby railroad workers. Dan married Lamon's eldest daughter, Isabella, in 1849 (yes, they were first cousins). In 1853, young Henry followed suit when Lamon Harkness' middle daughter, Mary, became his first wife. He was twenty-three and she was twenty and they were married in her father's home.

Mary Harkness had been frail since childhood and her father often sent to a boarding school Savannah, Georgia as a means of sparing her from harsh northern winters. Despite her frail health, though, she was the only one of Henry Flagler's three wives to bear him any children. Mary and Henry's first child was Jennie Louise (born March 1855), then Carrie (born June 1858 and named after Henry Flagler's older half-sister, Caroline), then finally, Harry Flagler (born December 1870). 

Harry Flagler was the only of Henry Flagler's children who outlived their father. Middle child Carrie died just before Christmas in the same year that Henry's mother died (1861). Eldest daughter Jennie Louise died when she was a young woman (more on her later).

The American Civil War

When the Civil War broke out, Dan Harkness was among the first in Bellevue, Ohio to enlist in the Union efforts. However, Henry Flagler did not join his half-brother. Even when a draft was issued in 1862, requiring American men 18 to 45 to join the service, Henry Flagler did not join the military. This was the case for many wealthy men during the Civil War, including Henry's future business partner, John D. Rockefeller. Indeed, there was a legal loophole provided to affluent Americans — they were allowed to pay $300 to the government and hire a substitute to serve in their place. According to historian David Leon Chandler, Henry Flagler is believed to either have bought a deferment in 1862 or provided the government supplies instead of service. Whatever the case may be, Flagler focused on his family and his fortune during the years of 1861 to 1865. 

Though Henry Flagler didn't join in on the war, it certainly affected his career choices. You see, demand for salt had risen with the beginning of the war — it was necessary for the preservation of food for the troops. As such, the salt industry was tax-exempt during the Civil War and essential employees were exempt from the draft. Dazzled by the prospect of tremendous wealth and supported by his father-in-law, Flagler followed the smell of money to Michigan. However, the boom did not last. Having had no prior experience in the salt industry, the Flagler & York company flopped and Henry lost around $100,000 ($100K in 1865 is nearly $2 million in 2022). Tail tucked in shame, the destitute Flagler family moved back to Ohio in January of 1866. 

Thus began an era of Flagler's life that he never spoke about to the press — one of scrimping and scraping. Perhaps those years after the Civil War were what imbued Flagler with his infamously shrewd business practices. It was that shrewd attitude that caught the eye of one John D. Rockefeller.

Standard Oil 

In 1869, Henry Flagler began buying out small oil refineries on behalf of John D. Rockefeller, who had it in his mind to monopolize the oil industry in Ohio. This was the beginning of the Standard Oil company, which would catapult both men into unimaginable levels of wealth. In January of 1870 at the age of 40, Flagler officially co-founded Standard Oil alongside John D. Rockefeller. Their efforts to monopolize the oil industry are referred to as the 'Cleveland Massacre,' and though John D. Rockefeller is generally more well-known than Henry Flagler, quotes from Rockefeller credit Flagler with the monopolization idea. 

As success quickly mounted for the young corporation, Flagler began to better provide for his family, moving them to Euclid Avenue in Cleveland, Ohio. In the springtime of 1870, Mary Harkness Flagler even became pregnant with the couple's third child (the aforementioned Henry "Harry" Flagler).

It seemed a new leaf was turning for the little family of the Robber Baron. However, a great cloud of bad luck was soon to fall over the Flagler family. When son Harry Harkness Flagler was born in December of 1870, Mary's frail health was greatly weakened by giving birth. As elated as the couple was to meet their first and only son, her condition made planning for Harry's future feel disturbingly somber.

Flagler's First Step Into Florida 

As the 1870s progressed, Henry Flagler, John D. Rockefeller, and their families began to move from Cleveland to New York and back again about twice a year — such were the demands of their beloved business. 

Throughout it all, Mary was made to brave her condition without her husband, who had taken to staying at the Buckingham Hotel in New York, completely immersed in the business of Standard Oil. Soon after, though, Mary and Harry followed. Racked with bronchitis and unable to do much for herself, Mary joined Henry in the Buckingham Hotel. 

Indeed, Mary Harkness Flagler's ailments first brought Henry Flagler to Far Florida. The same year that she arrived in New York, her doctors insisted that she spend the winter in a kinder climate. So, the Flagler family (Henry, Mary, little Harry, Jennie, and her first husband, John Arthur Hinckley) spent the winter of 1877-1878 in St. Augustine. 

Because Henry Flagler had not yet claimed Florida as his own, Savannah, Georgia was considered to be the last bastion of civilization on the East Coast. The swamplands south of Savannah were thought of as a dangerous land of rugged enchantment — where alligators lurked in the shadows and strange miasme was thought to carry diseases like yellow fever through the damp air. The voyage was harrowing and long — northern tourists traveled by railroad, steamship, and mule-driven omnibus. (To get a first-hand account of the journey from New York to St. Augustine, visit our page on Constance Fenimore Woolson's article "The Ancient City — In Two Parts," which was published in Harper's New Monthly Magazine in 1874.) 

While many tourists were satisfied with the charms of rural Florida, the appeal quickly wore off for the Flaglers, Henry specifically. The future "founder" of Florida found St. Augustine to be dirty, depressing, and worst of all — boring. After a few short weeks, the family all moved back to New York, much to the detriment of Mary Harkness Flagler's health, which got progressively worse in the coming years. She endured three more frigid northern winters until in 1881, when at the age of forty-eight, Mary Harkness Flagler died. Her eldest daughter, Jennie Louise, was twenty- six. Harry, her son, was eleven years old. Her husband, Henry Morrison Flagler, was fifty-one years old.

Despite (or perhaps because of) the tragic death of the mother of his children, Henry Flagler poured himself into the business of Standard Oil. During the early 1880s, Flagler outsourced the care of young Harry to his half-sister Carrie and daughter Jennie Louise. In a few years, it seems he embraced the life of a wealthy widower.

Second Marriage, Second Sojourn to St. Augustine 

After a time, Flagler began to turn over some of his duties at Standard Oil to younger blood. Instead of attending lunch with his fellow businessmen, he took to hosting grand parties at his new summer estate (which was ominously named "Satan's Toe"). The rumor mill suspected that this change in priorities was due to Henry's association with one Ida Alice Shourds — a red-haired, green-eyed actress who was rumored to have been Mary Harkness Flagler's nursemaid during her final years. (However, when Harry Flagler was asked about this later, he denied that Ida Alice had ever been his mother's nurse.) 

Ida Alice Shourds became Ida Alice Shourds Flagler in June of 1883 and moved into the Flagler family home the day after their wedding. Immediately, she began taking advantage of the fortune she had married into — like any budding socialite, she loved gowns, jewelry, and yachts. Although not much is known about Ida Alice Flagler, many sources claim she became fond of opulent parties and leisurely pursuits that were available to the fabulously wealthy. 

In February of 1885, the couple took a delayed honeymoon to St. Augustine — Ida Alice was thirty-seven and Henry Flagler was fifty-five. Luckily, the couple found the city to be even more promising than before. Indeed, Flagler's second sojourn to St. Augustine went off without a hitch — the recently constructed San Marco hotel accommodated him and Ida Alice well, and he found himself to be amongst peers instead of invalids. Bostonian Franklin W. Smith had recently built his winter home, the Villa Zorayda, which caught Flagler's eye almost immediately. The Zorayda's poured coquina and concrete structure, Spanish architecture, and lavish interior inspired Flagler, who actually tried to buy the building, but was denied. 

Flagler also met one Dr. Andrew Anderson, who would almost immediately become a lifelong partner and friend. Anderson owned a large tract of orange groves west of the Governor's House along King Street — the main thoroughfare of St. Augustine — and wanted to sell it to Flagler. On the condition that Anderson get the city's streets paved, Henry Flagler agreed to buy a portion of that land. He planned to build a hotel on that land, one that gave Northern tourists a fine place to spend their money. From there on out, Dr. Anderson was a major supporter and confidant of Henry Flagler, often acting as his business liaison in St. Augustine when Flagler was out of town. 

All this is to say that the winter and spring of 1885 were life-changing for Henry Flagler and his circle. He had caught the smell of opportunity in Florida and would eventually follow it all the way south to Key West.

Prince of Hotels: Laying Claim to St. Augustine 

The year was 1885, the month was April — and things were just getting started. Having bought land for the hotel, Flagler's goal was to build a pleasure palace and turn St. Augustine, Florida, into a 'Winter Newport'. 

First, Dr. Anderson worked through the bureaucracy to get Flagler approval to fill in the marshland that was west of the original town plan. 

Flagler engaged Thomas Hastings and Jean Carrere of the Carrere & Hastings architectural firm to design the hotel. McGuire & McDonald were in charge of construction. Louis Comfort Tiffany (who was about ten years into his monumental career) was hired to decorate the hotel and craft its windows. And even Thomas Edison had his hand in this project, having been responsible for wiring the entirety of the Hotel Ponce de Leon with electricity.

Many people were curious about Henry Flagler's decision to launch a new business venture during his twilight years. According to Florida historian Thomas Graham in his book The Awakening of St. Augustine, an acquaintance of the businessman once inquired about whether his judgment was sound when he decided to invest in Florida (one can imagine that they may not have been acquaintances for very long afterward). Flagler is quoted to have responded thusly: 

"There was once a good church member who had always lived a correct life until well advanced in years. One day when very old he went on a drunken spree. While in this state he met his good pastor, to whom, being soundly upbraided for his condition, he replied, 'I've been giving all my days to the Lord hitherto, and now I'm taking one for myself. This is somewhat my case. For about fourteen or fifteen years, I have devoted my time exclusively to business, and now I am pleasing myself.'" 

In fact, Henry Flagler was so pleased with his Florida projects that he began the construction of a second hotel, just across the street from the Ponce de Leon. It was initially intended to house entertainment amenities for the Ponce de Leon guests but was soon reimagined as its own hotel. One of Flagler's other St. Augustine Hotels, the Casa Monica, was originally built by Franklin W. Smith, who built the Villa Zorayda. However, Smith had fallen on some hard times and sold the hotel to Henry Flagler not long after it opened in 1888. Flagler renamed it the Hotel Cordova, after the street that it was on.

The Alcazar Hotel and Casa Monica Hotel have their own fascinating histories. The Hotel Alcazar is now the location of St. Augustine City Hall and the Lightner Museum, and the Casa Monica Hotel is still in business to this day. To learn more about the history of those buildings, visit the Alcazar Hotel Historical Place profile or the Casa Monica Hotel Historical Place profile on our website. 

St. Augustine city officials and businessmen were mostly grateful that Henry Flagler had chosen their little hamlet to 'please himself' by developing it and filling it with tourists. In general, government officials (especially Andrew Anderson) permitted Flagler to widen the roads and to dredge marshes to establish neighborhoods. He was even given permission to use the coquina quarry on Anastasia Island to source materials for his state-of-the-art hotels. 

However, many other officials were wary of Henry Flagler. They were rightfully concerned about allowing a wildly wealthy individual to have that much control over the public works of St. Augustine. In fact, this was a struggle that was occurring all over the country. During the Gilded Age, this new class of robber barons like Flagler, Rockefeller, Carnegie, and Vanderbilt were shaking up American society. Municipal, State, and Federal government officials questioned how many limits they should place on these "Captains of Industry." It seems that if too many limits had been placed on Henry Flagler's projects, St. Augustine would not be the city we know today.

In just eighteen months of harried work and lavish spending, the Ponce de Leon Hotel was opened for business in January of 1888. 

Enamoured by what Henry Flagler had been up to down south, droves of rich tourists made that harrowing journey to St. Augustine. Those first two seasons — during which Flagler hosted an innumerable amount of parties, electric light displays, and opulent dinners (all of which were accompanied by music from the best musicians of the time) — were met with eager approval by guests and the press. 

As you can tell, Flagler spared no expense in constructing the Ponce de Leon Hotel, sometimes called 'The Prince of Hotels' by newspapers of the time. To get a more in-depth narrative of the life of that building complex, visit The Ponce de Leon Hotel's Historical Place profile on our website. 

Then, just a few months before the end of the Ponce de Leon Hotel's second season, Jennie Louise Flagler Benedict died from complications of childbirth. She had been en route to St. Augustine from Charleston, South Carolina on the schooner Oneida. To add to the tragic circumstances, her baby daughter also died. Struck by the tragic loss of his eldest daughter and first granddaughter, Henry Flagler sought solace in his business projects and the council of friends like Dr. Andrew Anderson.

First Divorce + Third Wife = Scandal 

Along with the Ponce de Leon Hotel complex (which included four buildings in total), Flagler was also spending money on the construction of several other projects, including an estate for himself and his second wife, Ida Alice Flagler. Their estate was called Kirkside and was built west of the Ponce de Leon property. However, this building's history is tragic and short. For a time, Ida Alice and Henry Flagler both stayed and entertained guests within Kirkside, but trouble was on the horizon for Flagler and his second wife.

Over the course of her marriage to Henry Flagler, Ida Alice Shourds is reported to have begun displaying unstable behavior — she was rumored to have a temper, and her fondness for lavish parties and attention did not go unnoticed by Gilded Age Society. An incident that is commonly cited as being 'the straw that broke the camel's back' occurred on one of the Flaglers' expensive yachts (of which the couple had many — the Alicia was even named after Ida Alice). One stormy night, Alice is said to have nearly caused a shipwreck by not allowing the captain to return to port for several hours, despite experiencing gale-force winds and seasick friends. 

(Context from a 21st-century author: This story takes place nearly two generations before women were granted the right to vote — a time when we were generally valued for being subservient, delicate, and fertile. Those who failed to fulfill these expectations were often punished for it. You see, during the Gilded Age [and for far too long after it], women could be sent to a mental institution for just about anything. Asylum records from this era show women being admitted and held for ailments such as "suppressed menses", "mental {or} religious excitement", and the infamous catch-all "hysteria". 

Along with that, Henry Flagler being referred to as a 'Robber Baron' alongside businessmen like Carnegie and Rockefeller is no exaggeration. Flagler controlled a vast fortune, which he earned by buying out small oil refineries and creating a monopoly with Standard Oil. He was connected with government officials and industry elites. He even owned newspapers in Florida. So, when sources from the time period say that Ida Alice Shourds Flagler was insane, one must look closely and think critically. 

Last (and perhaps most importantly), the truth is a hard thing to garner when it comes to what happened in the past — even harder than it is today. Barely any of Ida Alice's personal writings have survived, so there is a major piece of the puzzle missing. Imagine how many different perspectives a group of people can have about the same topic. Now, imagine two hundred-plus years have passed. Researching those perspectives is like playing the telephone game with the dead; something is bound to get confused.) 

After two years of institutionalization and much assessment by the courts, Ida Alice Shourds Flagler was legally ruled incurably insane in 1899. She lived the rest of her life in New York, under strict supervision by her guardians (who were chosen by Flagler, of course). Henry Flagler didn't leave the sanitarium wanting, however, as Alice's estate (to which only her Flagler-hired guardians had direct access) was full of Standard Oil stocks. However, much to Flagler's chagrin, he had no legal grounds to be granted a divorce from Alice — in New York or Florida. At least, not yet. Henry started spending a great deal more time in Florida, soon claiming the state as his permanent residence. His attention was consumed by the business of his hotel chains and expanding railroad empire. Not to mention a talented young woman named Mary Lily.

Brief Interlude: Troubles between Father & Son 

In the case of Henry Flagler's life, it seems his personal troubles compounded in the 1890s. Along with the mounting unrest between himself and Ida Alice, Flagler was also butting heads with his son, Harry. While the younger Flagler wanted to pursue a career in music, Henry hardly thought that was appropriate for his only son and heir. This conflict created a breach between father and son that lasted until Henry Flagler was on his deathbed. To add to the sting, Henry 'Harry' Flagler was generally known as Harry Harkness, showing more deference for his mother than his father.

As we know, Flagler's business activity in Florida had earned him the attention of the public as well as state officials. Perhaps because of the economic success that Flagler's industries had delivered to the state or perhaps because of direct funding being delivered to individual senators, Flagler was able to convince the legislature to pass a little bill for him in April of 1901. Nothing major — just language that "[made] incurable insanity a ground for divorce." 

The public and the media in Florida exploded with the scandal of it all. That craze mounted when two months later, Flagler filed for divorce in Dade County and was granted such on August 13th, 1901. Craze became frenzy when Mary Lily Kenan and Henry Flagler married on August 24th, 1901. Henry Flagler was seventy-one, whilst his beaming bride was thirty-four. She and her family were given expensive gifts by Henry Flagler in celebration. 

Florida Eastcoast Railroad 

Henry Flagler's most monumental accomplishment was realized only a year before he died. His project to connect the east coast of the United States from top to bottom was completed when the first Florida East Coast Railway car pulled into Key West in 1912. This 'FEC' project had been underway since the late 1880s, when Flagler purchased the St. Augustine & Halifax Railroad in Jacksonville.

After construction for the Ponce de Leon and the Alcazar were underway in St. Augustine, Flagler's railroad properties started to expand southwards. As he went, Flagler spent exorbitant amounts of money to build hotels in certain cities along the way. Here is a list of Flagler's hotels (that he either purchased or built) along Florida's east coast: 

• 1888: The Ponce de Leon Hotel in St. Augustine 
• 1888: The Casa Monica/ Cordova Hotel in St. Augustine 
• 1889: The Alcazar Hotel in St. Augustine 
• 1890: The Hotel Ormond in Daytona 
• 1894: The Royal Poinciana Hotel in Palm Beach (on Lake Worth) 
• 1897: The Royal Palm Hotel on the banks of the Miami River 
• 1901: The Breakers Hotel in Palm Beach (on the Atlantic Coast) 

To learn more about Henry Flagler's East Coast Railway, consult the 'Works Referenced' section at the end of this Historical Person profile.

Henry Flagler's Death 

Along with cheques and stocks, Flagler also gifted his wife with a new estate in Palm Beach, Florida. The grand marble building was named by the final Mrs. Flagler herself: "Whitehall." It was here where Flagler would host his final parties and conduct his final business transactions. In 1913, Henry Flagler passed away after breaking his hip falling down a staircase at Whitehall. He was 83 years old. 

Though he didn't recognize him through his medicinal stupor, Henry Flagler's only son, Harry Harkness, was at his father's bedside alongside Mary Lily Kenan Flagler, whom Harry was actually meeting for the first time. 

Mary Lily Kenan Flagler inherited the majority of Henry Flagler's fortune but was unlucky enough to die of an apparent heart attack, only five years after Flagler's death. Her great-nephew Lawrence Louis Junior utilized some of those funds in founding Flagler College, where Henry Flagler's legacy lives on to this day.

Works Referenced in this Historical Person Profile

• Bowman, Bryan & Kathy Roberts Forde. "How Slave Labor Built the State of Florida — Decades After the Civil War." The Washington Post. May 17, 2018. 
• Castleden, Louise Decatur. The Early Years of The Ponce de Leon: Clippings from an Old Scrap Book of those days. From various newspapers, 1887 - 1895. 
• Chandler, David Leon. Henry Flagler: The Astonishing Life and Times of the Visionary Robber Baron Who Founded Florida. New York, NY: Macmillan Publishing Company, 1986. 
  • This is a major source for this Historical Person Profile — highly recommended! 
• Covert, Robert. "The Mary Lily Kenan Conspiracy." St. Augustine, FL: The St. Augustine Historical Society. https://staughs.com/the-mary-lily-kenan-conspiracy/ 
• The Flagler Museum Website, et al. 
• Graham, Thomas. "Flagler's Magnificent Hotel Ponce de Leon," FL: The Florida Historical Quarterly, Issue 54, Volume 1. July, 1975. pg. 1-17. 
• Graham, Thomas and Leslee F. Keys. Hotel Ponce de Leon: The Architecture & Decoration. St. Augustine, FL: Flagler College, 2013. 
• Graham, Thomas. The Awakening of Saint Augustine: The Anderson Family and the Oldest City: 1821-1924. St. Augustine, FL: Saint Augustine Historical Society, 1978. 
• Ralph, Julian. "Our Own Riviera," Harper's New Monthly Magazine. Volume 86, Number 514, 1893. 
• Reynolds, Charles B. The Standard Guide to St. Augustine. Originally published by E.H. Reynolds in St. Augustine Florida, 1892. Version accessed: St. Augustine, FL: Historic Print & Map Company, 2004. 
• Standiford, Les. Last Train to Paradise. New York, NY: Three Rivers Press & Crown Publishers, 2002. 

Bibliographic Citations for this Historical Person Profile

APA: VisitStAugustine.com. (2022) "Historical Person Profile: Henry Flagler." VisitStAugustine.com. 

MLA: VisitStAugustine.com. "Historical Person Profile: Henry Flagler." VisitStAugustine.com, 2022. 

Chicago: VisitStAugustine.com. "Historical Person Profile: Henry Flagler." VisitStAugustine.com. (2022).