The Shadowed Empire: Henry Flagler's Doomed Wives and the Curse of His Fortune
by M.P. Pellicer | Noir Notebook
Stories, legends, and myths swirl around Henry Flagler’s audacious railroad through the Florida wilderness. Yet the most haunting chapter remains his three marriages and the sinister dispersal of his vast fortune.
The First Mrs. Flagler
Henry Morrison Flagler left home at fourteen with only an eighth-grade education and clawed his way to unimaginable wealth. Alongside John D. Rockefeller, he co-founded Standard Oil of Ohio and became one of the richest men alive.
In 1853, he married Mary Harkness. They had three children—Jennie Louise, Carrie, and Henry Harkness—yet only Henry Harkness survived to continue the bloodline. By the 1870s, Mary suffered crippling bronchitis. Doctors prescribed Florida’s warm climate, especially during New York’s brutal winters. The couple visited in 1876, but Flagler, obsessed with New York’s business world, refused to return to Florida. Despite her doctor’s orders, she stayed in New York with her husband. She died May 18, 1881, from tuberculosis.
Whether remorse gnawed at Flagler for hastening his invalid wife’s death remains unknown. A new obsession quickly silenced any prick of conscience.
Mad Alice Flagler
In true gothic fashion, the 51-year-old widower soon married his late wife’s 33-year-old nurse, Ida Alice Shourds, eighteen years his junior. She was the daughter of an Episcopalian minister who grew up in modest circumstances. She flirted with acting and drifted into nursing, which led to her position as Mary Flagler’s nurse. Rumors whispered she had already warmed Flagler’s bed before the vows.
They wed in 1883 and honeymooned in St. Augustine, the future site of his opulent Ponce de Leon Hotel. By the early 1890s, her behavior began to change. Flagler discovered his wife’s fascination with spiritualism concealed a fractured mind. Alice, as she was known by family and friends, who was already known for an acerbic tongue, grew more vicious and unhinged. At a yacht party, she demanded they remain at sea despite a raging storm that endangered everyone aboard. She openly declared she must murder Flagler so she could marry Czar Nicholas II, who, she insisted, loved her madly. The Ouija board, conveniently, never warned her that the entire Romanov family would perish before Bolshevik bullets in 1918.
Alice also broadcast Flagler’s infidelities—topics forbidden in polite society. Scandal rippled through high circles about Flagler’s mad wife.
According to the book, Florida’s Flagler, Henry Flagler, enlisted the aid of Dr. George G. Shelton. The physician made sure to be around when Alice exercised her “glib tongue” and witnessed her diatribes. This was in preparation for declaring Ida Alice Flagler insane.
It was reported that Alice once went after her doctor with a pair of scissors, but there is speculation that Mrs. Flagler’s symptoms were exaggerated to have her committed.
The men had known each other since Dr. Shelton had attended Flagler’s daughter, Jennie Benedict, when she gave birth to a baby girl who died within hours on February 9, 1889. Jennie Benedict followed her daughter to the grave a month later. She died at sea, off the coast of South Carolina, on board the yacht Oneida. She was on her way to visit her father in St. Augustine. It’s not known if her death was due to complications after childbirth or another cause.
Flagler went on to build the Memorial Presbyterian Church for Jennie and her baby, Margery, in St. Augustine. This left Flagler with only one child alive, his son Harry. He had already lost his other daughter, Carrie, in 1861, when she was three years old
By 1895, two alienists examined Alice Flagler. She became frantic, and they declared her insane. Authorities committed Alice first to Pleasantville Sanitarium, then to Flagler’s mansion at Satan’s Toe on Orient Point, where ten servants and Dr. Shelton attended her. This marked the final time Henry Flagler saw his second wife.
While Alice spiraled, Flagler poured his fortune into Florida, transforming it into the American Riviera. He erected the lavish Ponce de Leon, the colossal Royal Poinciana on Lake Worth, and the oceanfront Palm Beach Inn—later the Breakers.
Eventually, Alice came under the care of Dr. Carlos Frederick MacDonald, the president of the New York Commission in Lunacy, and the state’s leading alienist. He left this post to take over the Choate House, a private sanitarium that catered only to wealthy clients. He remained Alice Flagler’s doctor until he died in 1926.
Dr. MacDonald specialized in the criminally insane. In 1889, he participated in the design of New York’s first electric chair, claiming it was more humane than hanging. He practiced on dogs and horses. In 1891, he supervised the first 1500-volt execution of a prisoner at Sing Sing, noting that there was “no burning of flesh but some blisters…”
Mary Lily, the Last Wife
Meanwhile, a much younger woman captured his eye: Mary Lily Kenan, born in 1867. Despite a 37-year age gap, the fading spinster and the tycoon began a scandalous affair. Rumors claimed she bore him an illegitimate daughter in 1895, whom her sister Jessie Wise quietly raised.
In 1896, Flagler gifted his mistress with $1 million in Standard Oil stock, and her sister Jessie with a house, a parcel of land, and 200 shares of Standard Oil stock. Perhaps this was in repayment for taking care of his unacknowledged daughter, named Mary Louise.
Yet Alice still lived. Divorce for insanity proved impossible in New York or Florida. It seems that Alice Flagler might have been crazy, but she wasn’t wrong when she described her husband as a philanderer of the first order.
The Gilded Scandal of Henry Flagler and Helen Foote
It appeared that whatever machinations Flagler was orchestrating to gain his freedom were not a secret. Henry Flagler may have owned the Florida East Coast’s major newspapers and been able to influence New York papers, but he could not censor Florida’s other newspapers that ran an exposé on Flagler’s dalliance shortly before his wedding to Mary Lily.
In a small insert published by The Tampa Tribune on May 12, 1901, one chilling line hinted at the storm gathering around the railroad magnate: “The husband of a pretty New York woman is suing Mr. Flagler for alienating his wife’s affections. This may furnish more work for the Florida legislature.”
The remark suggested that Flagler’s political maneuvering had already become an open secret. Rumors swirled through New York society that the wealthy industrialist intended to free himself from his marriage by any means necessary.
According to gossip circulating among Manhattan elites, Flagler first noticed Helen Foote while she sat inside a private box at the Metropolitan Opera House. Captivated, he arranged an introduction. What followed ignited one of the Gilded Age’s most whispered-about scandals.
Edward C. Foote later accused his wife of carrying on an intimate relationship with Flagler aboard the yacht Alicia in June 1897. During the same period, Flagler also pursued an affair with Mary Lily Kenan, deepening the intrigue surrounding his private life.
Helen Foote, already separated from her husband, attracted admirers wherever she traveled. One of the most devoted, John H. “Jack” Malden, stayed at her parents’ New York boarding house and quickly fell in love with her. Malden dreamed of marrying Helen once she secured a divorce. His fascination deepened after she casually revealed a crisp $1,000 bill—an astonishing sum at the time. She was elusive as to the source, only claiming she had come by it through honest means.
Because Helen’s parents disapproved of her lavish lifestyle, she invited Malden to accompany her while she searched for a fashionable apartment and expensive furnishings. She secured an elegant apartment on East 58th Street near Fifth Avenue.
In his lawsuit, Edward Foote alleged that Flagler had become “the author of his wife’s prosperity.” He claimed the millionaire supplied Helen with enormous sums of cash and marketable securities, including Standard Oil certificates reportedly worth $400,000. Foote further alleged that Flagler rented a residence for Helen on East 57th Street near Madison Avenue and personally covered the staggering $4,200 annual rent.
Helen embraced the lifestyle completely. She traveled through Europe three times, purchased extravagant gowns, and spent recklessly while Malden accompanied her across the continent. Eventually, however, their relationship cooled. Helen dismissed him as nothing more than a brother.
Malden spiraled after the rejection. Crushed and humiliated, he squandered nearly $20,000 within a single year and ultimately served six months in the Tombs prison for passing fraudulent checks.
The affair’s icy conclusion coincided with a controversial bill that swept through the Florida legislature. The law declared insanity legal grounds for divorce, and many observers believed Flagler himself had engineered the measure to escape his marriage. Helen apparently believed she would soon become the next Mrs. Flagler.
Anticipating she would need to free herself from the legal bonds of matrimony, she relocated to Sioux Falls, a city notorious at the time for its quick divorces. After living there for six months, she secured a divorce from Edward Foote in December 1900 on the grounds of abandonment.
Edward Foote immediately challenged the validity of the divorce in court, further dragging the scandal into public view.
When Helen returned to New York, she expected Flagler to finally claim her openly. Instead, he drifted away. Society insiders whispered that her greatest appeal had always rested in her status as another man’s wife—a perfect arrangement for a hidden affair, but not for marriage.
Now calling herself Helen Long, she recognized the truth before the newspapers fully exposed it. Whatever promises Flagler may have made had evaporated. Abandoned by the man whose fortune had transformed her life, she eventually married J. O’Bannon, a businessman who operated a schoolbook supply company.
The scandal faded into history, as no doubt Henry Flagler made some type of private settlement with Mr. Foote, and Helen O’Bannon recognized her moment in the sun was over.
Shadows of ambition, wealth, and betrayal still lingered around Henry Flagler’s gilded empire.
Having established his residence in Florida since 1899, on August 14, 1901, he divorced his legally insane second wife and established a $1 million trust for her care. Alice outlived them all, dying of a brain hemorrhage in 1930 with her trust swollen to $12 million.
Just two weeks after the divorce, on August 24, 1901, Flagler married his mistress, Mary Lily Kenan.
Dr. MacDonald and Alice Flagler
In 1902, Dr. MacDonald decided to move Alice Flagler to a mansion named The Orchard in New Rochelle. This was an effort to change her surroundings, and she lived there for the next two years. She was described as still young and beautiful, though white-haired. “She still believes she is engaged to the Czar of Russia; on all other subjects, she converses rationally. To one unacquainted with her delusion, if the subject is not brought up, Mrs. Flagler appears perfectly sane.”
A year later, Henry and Mary Lily came to stay at their home on Orient Point, only four miles away from The Orchard. He was suffering from lumbago, and she had a “nervous disease”.
Eventually, Alice Flagler was moved to Dr. MacDonald’s private sanitarium, known as Dr. MacDonald’s House. He was paid handsomely from her trust through the years. In 1912, The New York Sun reported, “Mrs. Flagler makes frequent trips to New York and attends the opera in the winter.”
Despite Alice Flagler’s appearance of not being a raving lunatic, Dr. MacDonald continued to assert she was “incurably insane.” Perhaps his insistence on this diagnosis was fed by the steady stream of money from Alice’s trust. He had raised his fee considerably. Her estate also supported a score of nieces, nephews, cousins, and second cousins who petitioned the court for monthly stipends. Since 1902, her sister and two brothers each received $4,000 yearly; three nieces and nephews received $1,330.
It was obvious that Alice Flagler was worth more insane than cured, and her dilusion that the Russian Czar was in love with her was quite tame compared to other lunatics Dr. MacDonald assessed.
In 1906, he saw himself embroiled in the trial of millionaire Harry Thaw, who killed architect Stanford White over the affection of his wife, Evelyn Nesbit, who was once White’s mistress and was known as The Gibson Girl.
He examined Leon F. Czolgosz, assassin of President William McKinley, and Eric Muenter (a.k.a. Frank Holt), who shot J. P. Morgan. Only hours after Dr. MacDonald completed his preliminary interview with Muenter, the accused committed suicide by leaping from the top rail of his jail cell, plunging headfirst onto a concrete walkway, resulting in a skull fracture.
He was also a witness at the hearing on the sanity of Harrison W. Noel, the “Montclair Slayer.”
The Strange Death of Mary Lily Flagler
In 1902, Henry Flagler presented his new bride with Whitehall, a breathtaking, Gilded Age, 55-room, 60,000-square-foot Palm Beach palace designed by Carrère and Hastings. A hidden staircase allowed Flagler to slip away from tedious parties. In 1913, he fell on those very stairs, broke his hip, and died at 83. He left Mary Lily $108 million and was buried beside his first wife, Mary Harkness.
Mary Lily’s own story proved equally cursed. Her family, the Kenans, intertwined with the Binghams through UNC, the Revolutionary War, and the shadowy Order of the Gimghouls—whose watchwords were “midnight, graves, and weirdness.” Years earlier, she had shared a passionate romance with Robert Worth “Rob” Bingham, but family feuds tore them apart. She turned instead to Flagler.
After UNC Bingham attended the University of Virginia, without graduating. He then went to Louisville, Kentucky.
In 1896, he married Eleanor Miller, who came from a wealthy family and was politically prominent in Louisville. The next year, he received his degree in law from the University of Louisville. In 1911, he was appointed to the Jefferson Circuit Court and was known as Judge Bingham for the rest of his life.
His wife, Eleanor, committed suicide in April 1913 by jumping out of the car she traveled in as it crossed railroad tracks. She was accompanied by her brother Dennis Long Bingham, who was driving the automobile, and her 3 children, who witnessed her horrific act. She died later in the hospital after “an eastbound Louisville and Interurban car struck the big six-cylinder automobile at O’Bannon Station.” She was 42 years old. Her father, Samuel Miller, had ended his life the same way 19 years before.
Three weeks after Mrs. Bingham ended her life, Henry Flagler died, leaving Mary Lily Flagler one of the wealthiest women in the United States. Judge Bingham, in contrast, was buried in debt, which perhaps explains why he looked up his old lover.
They married in November, 1916, in a private ceremony with her “niece” Louise Wise as her only attendant. Before the wedding, Bingham signed a prenuptial agreement, giving up claim to the Flagler fortune should his wife die before him. Mary Flagler had publicly named Louise as heiress to the bulk of the Flagler fortune.
Within eight months, the 50-year-old heiress complained of chest pains. Bingham summoned not a cardiologist but his friend, dermatologist Dr. Michael Leo Ravitch. They dosed her with ever-increasing morphine in hotel rooms and at home. A Gimghoul lawyer helped her sign a codicil bequeathing $5 million to Bingham outright.
Mary Lily Bingham collapsed in her bathtub and started to convulse. Even after she was unconscious, she was given more morphine. She died on July 27, 1917, at the age of 50.
Her body contained opiate in abundance, plus traces of adrenaline and arsenic.
The Fate of the Binghams
Her family suspected foul play and arranged to exhume her body at midnight from a Wilmington cemetery. Three pathologists were hired to complete an autopsy at New York’s Bellevue Hospital. The family promised to make public the report, but instead locked away the findings. Speculation ran wild, and some believed Mary Bingham was addicted to laudanum and had overdosed.
Another rumor that circulated was that Robb Bingham threatened to tell the press that she had died from complications of syphilis if they continued to interfere, as well as her taste for brandy and bourbon. He used Shepard Bryan, another Gimghoul, as a go-between with the Kenan family.
Ironically, it was believed that Mary Lily contracted tertiary syphilis from Bingham, who had been infected while attending college. In those years, dermatologists treated syphilis, which is why Ravitch was his personal physician.
The reason given for her death was “acute heart disturbance”, but this did not quiet the whispers that spoke of murder and malpractice.
Bingham used his dead wife’s money to buy the Louisville Courier-Journal. He became ambassador to the Court of St. James, and died in 1937—possibly from syphilis or Hodgkin’s disease. Accusations of murder followed him to the grave.
Sallie Bingham, Robb Bingham’s granddaughter, acquired Mary Lily’s second autopsy report many years later, which concluded she died from an overdose of Salvarsan used to treat syphilis.
Robert Bingham would go on to marry a third time. Her name was Aleen Lithgow Hilliard, the widow of a wealthy stockbroker. She outlived him by 16 years.
Ironically, Robb Bingham’s cohort in what might have been murder was supposedly a staunch anti-capitalist and enemy of the millionaire class. He was a Russian Jew whose family had fled to the United States.
He had come to Louisville in 1896 and had a meager private practice, “obtaining most of his income from politically appointed jobs on the teaching faculty at the University of Louisville and on the medical staff of the Eastern Kentucky Asylum in Lexington.”
He lived with his wife and daughter in an apartment in a lower-middle-class neighborhood, which begs the question, why would Bingham, who was able to afford the best medical help in the country, call on him?
In 1937, he authored a book, The Romance of Russian Medicine. He wrote in the book: “Russia is showing the way to a real democracy, where riches and class distinctions are banished and where life is made happier and more satisfying.”
Sallie wrote that Judge Bingham bought the newspaper “to ferret out other people’s secrets while closely guarding our own. (Mary Lily) died … of a combination of causes that included depression, neglect and medical incompetence, the failure of love, isolation, and a heart probably weakened by the syphilis she had contracted from the Judge… She also died because she would not, for a long time, give the man his money.”
Emily Bingham, Robert Bingham’s great-granddaughter, wrote in her book that “Roosevelt himself gleefully called his ambassador ‘my favorite murderer'”. She also described where Dr. Ravitch demanded money from Bingham, writing, “I am really sorry that I ever consented to do for you what I did.”
Judge Bingham’s great-grandson, Robert Worth Bingham IV, died from a heroin overdose in 1999. He was 33 years old. His father, Robert Worth Bingham III, was killed in a freak accident in 1966. One summer morning, while vacationing with his family in Nantucket, he decided to drive to the beach to surf, placing his board horizontally across the backseat of his convertible. When one protruding end hit a parked car, the whole surfboard swung around and crushed his neck.
In 1987, Pulitzer Prize-winning author David Chandler wrote The Binghams of Louisville, which posits that Robb Bingham conspired with Dr. Michael Ravitch to get rid of his wife. Barry Bingham Sr. attempted to suppress Chandler’s book and spent a reported $500,000 in legal fees to stop the book from being published. The maneuver didn’t work.
Flagler’s Children: Harry and Mary Louise
The Flagler fortune continued its grim harvest.
Louise Wise, Henry Flagler’s “favorite niece,” inherited Whitehall in Palm Beach, Kirkside in St. Augustine, money, and securities.
Mary Louis married three times. She married Dr. Lawrence Lewis in 1917, only months before her aunt died. They had two children: a boy was named after his father, and a daughter named Mary Lily Flagler. They were already estranged when Mary Louis secured a divorce in 1925, based on desertion.
She married Hugh R. Lewis in January 1927, even though his family was opposed to the union. Hugh came from a wealthy family in his own right. His father was known as the Lumber King of Pennsylvania. They divorced in August, 1930.
Eight months later, she married Frederick Francis; it seems that luck in marriage was not in the stars for Mary Louise. The marriage ended in 1936.
On May 28, 1937, at the age of 40, Mary Louise died from an overdose of a sedative, allegedly taken through error, according to the official finding.
Henry Flagler’s son, Harry Harkness Flagler, was a businessman and philanthropist who spent his life promoting the New York art scene. He was the president of the Symphony Society of New York starting in 1914, one of many positions he held throughout his life. He gave money to the Symphony Orchestra to make it the first American orchestra to tour Europe.
He married Annie Louise Lamont in 1894. She was a millionaire heiress in her own right. They had three daughters, Mary, Elizabeth and Jean. They remained married until Annie’s death in 1939.
There were rumors that a rift opened up between Harry and his father when Henry Flagler married Ida Shourds. Harry, as the youngest of his siblings, was 11 years old when his mother died, and 13 when his father took a new bride. Perhaps he felt it was a betrayal of his mother’s memory.
There was another argument when he was an adult, when it seems he didn’t demonstrate any interest in his father’s railroad and Florida businesses. It was said that father and son had little to do with each other after this.
He died in 1952 at the age of 81.
Henry Flagler built an empire of sun-drenched palaces and iron rails, yet death, betrayal, and whispers of the occult clung to every dollar. Some fortunes, it seems, exact a price far darker than gold.
