
The Early Life of Henry Flagler
It was January 22, 1912, when Henry Flagler steamed into Key West aboard his private rail car – a hero. His Florida East Coast Railway had just completed the some-said-impossible task of connecting that southernmost key with Florida’s mainland by rail.


Flagler had just turned 82 on that momentous day when his train reached Key West – and his triumphant arrival was the culmination of what many think of as his career. He’d successfully extended the railroad down the whole east coast of Florida, dropping a series of luxurious hotels along the way. And he was rightfully proud of his accomplishments; the Royal Palm Hotel in Miami, for instance, was built in the shape of an “F”. And its peculiar mustard-hued paint was known as Flagler Yellow.
Surprisingly, to those who only know of his Florida business exploits, these were part of Flagler’s second career – something he didn’t even start until he was 55. Before that, he’d enjoyed a very different life as a business associate of John D. Rockefeller in Standard Oil. But the even earlier life of Henry Flagler . . . now, that’s a story most people don’t know at all — and it’s a fascinating one!

Flagler was born on January 2, 1830 to Elizabeth Caldwell Morrison Harkness Flagler. As you might suspect from those many surnames, Elizabeth was on her third marriage when she became Henry’s mother. Her first husband, Morrison, had left her a widow at the age of 20. Elizabeth’s second husband was David Harkness, a physician, who had moved to Ohio from upstate New York. His first wife had died, too, and he married Elizabeth soon after arriving. They would have one son together (Dan), but Harkness died in 1825, about four years after their marriage. Elizabeth returned to New York with her young son, living with her mother-in-law.
Three years later, in 1828, Elizabeth married for the third time, this time to a local Presbyterian minister named Isaac Flagler. Flagler, too, had already buried two spouses – his first wife had died in 1820, leaving him with two daughters; and although he remarried in 1824 (and had another daughter), Wife #2 had passed away three years later, in 1827. He married widow Elizabeth the very next year.
Before long, Isaac and Elizabeth Flagler moved to Hopewell, NY, another community in the Finger Lakes region. And that’s where Henry was born, just after New Year’s Day in 1830. Henry’s full name was Henry (in honor of his father’s brother); Morrison (after Elizabeth’s first husband); and of course Flagler after his dad.
By 1837 the family had moved again, this time settling in Toledo, Ohio — a frontier region where pastor Isaac Flagler functioned as a missionary minister. Henry Flagler was just 7 years old at the time they moved to Ohio. But whether by fate or by design, the remote location put Elizabeth’s first son, Dan (Henry’s half-brother), now 14, closer to his Harkness relatives. It was a family connection that would prove fortuitous for both boys.
The Harkness family were prosperous business folk who had built up a regional chain of country stores. And great change was afoot; a new railroad called the “Mad River & Lake Erie RR” had already been granted a charter to link the area with a port on Lake Erie. When that railroad was completed in 1839, the area quickly morphed into a commercial hub.
Isaac Flagler may not have found much ability to earn a livelihood there; by the late 1830s or early ’40s, he had accepted a new church job and moved his family back to New York. Even so, the finances of a parson’s family remained tight. By 1844, young Henry was eager to strike out on his own. By this time, Henry’s half-brother Dan Harkness was managing a Harkness family store in Republic, Ohio. And a plan was apparently hatched.
Fourteen-year-old Henry secured a job loading and unloading cargo for a canal boat on the Erie Canal, likely to cover the cost of his passage. That took him west to Buffalo NY, and from there into Ohio. When Henry finally stepped off the boat in Republic, Ohio (where his half-brother lived), he had four pennies, a nickel, and a French five-franc coin in his pocket. Henry would keep that larger coin for the rest of his life. His financial life had been launched — with all of nine cents.

Henry began helping his half-brother in the store at a wage of $5 a month. He was given free lodging in a back room, but in winter the space was freezing cold. At first, he and Dan wrapped themselves up in thin blankets for warmth, but eventually moved into the store itself, using wrapping paper as an additional covering at night.
Mercantile experience in the store taught Henry important lessons about supply, demand, and “what the market will bear.” When Henry dipped brandy from a keg for customers, for example, the price varied depending on the buyer. English patrons would pay $4.00 a gallon; German customers $1.50; and other customers were charged whatever Henry thought he could get.
Henry moved up in the world after four years at the store in Republic. About 1848, at the age of 18, he began working for a larger store in the Harkness family chain, this one in Bellevue, Ohio. Now instead of $5 a month, he was earning $33. In 1852, he became a partner with his half-brother Dan in “D.M. Harkness & Company.”
Life in Bellevue had its social side – Flagler and his half-brother played ten-pins (bowling) together, and would talk business over a beer. In late 1853, when he was 23, Henry married Mary Harkness, daughter of his not-quite-uncle, Lamon Harkness (brother of his mother’s deceased husband). A daughter was born to Henry and Mary in 1855, and a second daughter arrived in 1858. Henry’s parents moved to Bellevue as well.
The area was growing quickly, and the Harkness company expanded its business to include trading in grain. That endeavor led Henry Flagler to cross paths with John D. Rockefeller, then working as a Cleveland commission grain broker.
But it was liquor where the young Flagler made his first fortune. The Harkness Company’s assets included a distillery plant, and the company had plenty of grain. With Flagler now a partner, the company opted to boost the distillery’s capacity ten-fold. Now instead of using 60 bushels of grain a day, it went through 600 bushels.
Flagler’s pastor-father, however, was no friend to the liquor trade. In 1838, he’d been the first president of Toledo City’s Temperance Society. So it’s possible that after Isaac Flagler moved near his son, he convinced Henry to exit the liquor business. Whatever the rationale behind the decision, in 1858 Henry sold his interest in the distillery. But by then he had already made a small fortune on whiskey.
That same year (1858), Henry had a lavishly-ornamented “gingerbread” house built for Mary and his young daughters in an upscale Bellevue neighborhood. And although the Civil War broke out in 1860, Henry didn’t enlist; instead, he paid someone else to go in his place, a fairly common practice for the well-to-do. Half-brother Dan, however, did join the Union Army as a quartermaster, but returned home in 1863 to tend to his business. His presence would have been needed; by then, Henry was off to Saginaw, Michigan to pursue the salt trade.
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Like to read more of Flagler’s story? Here’s Part 2 and Part 3!
