Harry Harkness Flagler Was a Cool Dude

Harry Harkness Flagler Was a Cool Dude 1

Image from Dr. Tom Graham’s Mr. Flagler’s St. Augustine, 2014.

According to an undated article in the Savannah News, Henry M. Flagler did not like dudes. He had more respect for a donkey than a dude. What is a dude? In the late 1800s, they were defined as young men who flaunted flamboyant outfits in order to gain attention, another word for them was ‘dandy’. They were often referred to as “city slickers” by rural folk because these men would not be able to handle such “dirty work” as being a farmer or cowboy. Though some men defended being a dude as a phase, Flagler rebutted that a true dude never changed. Allegedly, Flagler could abide his son, Harry Harkness Flagler, to be anything but a dude. Unfortunately, Henry Flagler and Harry Harkness did have a falling out because Harry was not the kind of “dude” Henry wanted him to be.


Harry Harkness was born to Henry Flagler and Mary Harkness Flagler in 1870. Right from the start, Henry began making plans for Harry’s future. When he was ten-years-old, Harry was sent to Ohio to be with his Aunt Carrie while their home in New York was being renovated. At the same time, Mary Harkness was very ill. She sent Harry caring letters, but he rarely heard from his father.

In 1881, Mary succumbed to her illness and Henry convinced Carrie to become matron of the household, and to raise Harry. This was until 1883 when Henry married Ida Alice, who was Mary’s nurse before her death. Henry sent Carrie on a vacation for the remainder of the summer and she then moved to her own place in Manhattan. Harry did not receive his new stepmother well, feeling that his father was replacing his mother and aunt with her.

In 1892, Henry invited Harry to work at his hotels in St. Augustine after Harry dropped out of Princeton. Henry’s plan was to teach his son the ways of hotel management and the railroad, to have Harry succeed him. One year later, Henry announced that his manager at the Hotel Ponce de Leon resigned and Harry Harkness would be taking over responsibilities for all three of his hotels. This was the beginning of Henry introducing Harry into his succession. Henry either did not notice, or ignored, that his son was not interested in his business pursuits which caused conflict during his time in St. Augustine.

Harry had the hotel buildings repaired and repainted, knowing the importance of this maintenance. However, Harry’s main interest was in the casino at the Alcazar, which he worked during the 1895 season. He made changes that became profitable, such as not charging patrons admission and instead charging them to use the bath and for double daily concerts of a Hungarian band. Othewise, Harry refused to work with his father to fulfill his vision. While Henry increasingly wanted Harry to take on more duties, Harry was more interested in his own pursuits.

This conflict of interests caused a rift between father and son. Harry returned to New York where he enrolled at Columbia University and then married his sweetheart, Anne Lamont. The estrangement was not yet complete because Henry and Ida Alice attended the wedding. Over the next few years Harry would be involved in scandals that embarrassed his father, such as being arrested in 1896 as part of a bachelor party gone awry. Allegedly, the men had a couple of comedians at a club, they ordered several exotic dancers, and solicited the famed belly dancer “Little Egypt” to do a bawdy dance for them. Though all of the men were exonerated for ‘enticing Little Egypt into a lewd dance’, Henry could not abide by his son’s behavior.

Though it is unknown what the final incident was that caused their separation, father and son would go almost twenty years without speaking again. Out from under his father’s shadow, Harry Harkness flourished. Harry graduated from Columbia University in 1897, at age 26, and became an important figure in the New York music scene during the twentieth century. He became a principal financier and president of both the Symphony Society of New York and the Philharmonic-Symphony Society. As a patron of classical music, he used the skills he learned from his father to promote the cultural enhancement of the city.

The last time Harry Harkness would see his father would be on Henry’s deathbed in 1913. By the time he made it to his father’s side, Henry was in a coma and could not recognize his son. Unfortunately, they were unable to reconcile before his death.

According to Flagler’s doctor, Owen Kenan, “Harry Harkness Flagler was the nicest gentleman he had ever met” due to his kindness toward Flagler’s third wife, Mary Lily Kenan during the time of Flagler’s death. Flagler only left Harry a small portion of his estate feeling that Harry did not do enough for him to leave more. One family friend felt the rift occurred because Henry did not understand his son’s love of music. Flagler’s biographer, Sidney Walter Martin, mused that the reason was Flagler’s being too overbearing in dealing with Harry.

Harry’s wife, Anne Lamont, died in 1939 at their home in Millbrook New York. Harry Harkness Flagler died in 1952 of a heart attack at age 81.

Written by Nicole Diehm


Akin, Edward N. Flagler: Rockefeller partner and Florida baron. Kent, OH: Kent State University Press, 1988.

Castleden, Louise Decatur. “The Early Years of the Ponce De Leon”: Clipping from an old scrap book of those days kept by the First Manager of this “Prince of hotels”. St. Augustine, FL, 1958.

Chandler, David Leon. Henry Flagler: the astonishing life and times of the visionary robber baron who founded Florida. New York : Macmillan Publishing Company, 1986.

“Dude.” Wikipedia. Last edited on May 8, 2022. https://en.wikipedia.org/wiki/Dude#:~:text=The%20term%20%22dude%22%20may%20have,particular%20importance%20to%20his%20appearance. Accessed Aug 9, 2022.

Graham, Thomas. Mr. Flagler’s St. Augustine. Gainesville, FL: University Press of Florida, 2014.

Graham, Thomas. The Awakening of St. Augustine: The Anderson Family and the Oldest City 1821-1924. St. Augustine, FL: St. Augustine Historical Society, 1978.

Martin, Sidney Walter. Florida’s Flagler. Athens, GA: University of Georgia Press, 1949.