The Early Years
The Henry Phipps family’s prominent role in making South Florida an ultimate destination is not told as often as Henry Flagler’s fabled story though it makes for a more engaging, multifaceted narrative.
The tightknit Henry Phipps Jr. household preferred the Gilded Age reserve fortified by British castles and rustic Scottish hunting lodges, fancying Claridge’s afternoon tea or foregathers at Hotel Cecil with crown heads rather than rubbing elbows with their American peers at one of Newport’s social summits. And yet, no matter the aura emanated by entrance halls populated with suits of armor separating them from the outside world, the family’s immense wealth, mansion building, real estate roulette, and pursuit of the winner’s circle, made for the most publicized 20th-century private lives imaginable in Pittsburgh, New York, Chicago, Palm Beach, and London.


Even before their Carnegie Steel shares reaped a fortune from their merger with the newly formed conglomerate, Henry and Anne (Annie) Childs Shaffer Phipps had already broadened their horizons beyond Pittsburgh’s confines, where their conscientious philanthropy assured them immortal standing. In between uprooting from their Allegheny City digs and settling into a more cosmopolitan life found in an upper Fifth Avenue mansion and Long Island estate, they took up residency in Washington, leasing Albert and Alice Barney’s Italian palazzo on Rhode Island Avenue, around the corner from Charles and Carrie Munn’s Scott Circle quarters. When the New York mansion was completed, several newspapers identified them as “former Washingtonians,” their names already etched among the turn of the 20th-century’s most princely in the US and Europe.
Having opened their checkbook for General Louis Botha’s Boer War relief and Lord Curzon’s famine aid in Calcutta, they were tapped for royal introductions at St. James Palace for intimate Drawing Room presentations. When the family disembarked from the RMS Mauretania’s royal staterooms with 145 pieces of luggage and a 12-member staff, stepping down the gangplank onto a waiting private two-car train, the family was welcomed with international headlines.
While the Henry Phipps Institute contended with the White Plague, the Henry Phipps Estates’ apartments in New York set forward-looking standards. Years later, there were no self-effacing gestures when family members boarded a helicopter to see their thoroughbreds run in three races on the same afternoon held on three separate tracks located in three different states.

Just as Pittsburgh newspapers publicized the family’s every whistlestop for decades after their exodus, New York’s tabloids were equally enthusiastic, documenting their lives from Long Island horse shows to the latest commercial real estate transaction. And in much the same Medici to Vanderbilt tradition, they built mansions that expressed their good fortune.
Having paid $450,000 for a prized parcel three blocks south of Andrew Carnegie’s marble mansion and spending as much as a million to build their Fifth Avenue villa, the Phipps family began acquiring other Fifth Avenue properties located at 96th and 102nd Street, as well as nearby commercial properties, according to the 1901 New York Real Estate Record.
In concert with their legacy, the properties were acquired under the name of their oldest son John S. Phipps (Yale, 1898) who also bought a farm on Long Island in Old Westbury where several years later he and his wife Margarita built Westbury House.


Society columnists aired family celebrations and comings-and-goings, posted by private secretaries armed with luncheon guestlists, dinner menus, and the latest charitable war efforts. Sporting pages captured their every win-place-show, fairway drive, and serve. While guest rooms might have quartered tennis pros brought in from New York and London, prepping them for the Palm Beach’s annual tennis tournaments, there was also Annie and Amy’s leading role as women’s rights advocates, marching in the frontlines of suffragist demonstrations and serving as vice-presidents of South Florida’s Equal Suffrage League.
From Chicago to Miami, the family’s large-scale residential and commercial projects placed them on front pages. For several of these speculative endeavors, they engaged planners Bennett, Parsons, and Frost, the nation’s eminent City Beautiful advocates. However, unlike many of their counterparts’ emphasis on the social climb, they maintained a disinterest for dazzle, however many flashbulbs blazed between chukkers, golf rounds, and finishing lines.
At any moment, a news story might have reported the Phipps family “ … live very quietly and do no entertaining of note.” While on the same page, another account stated: “Most of the Rolls Royces in the colony were gathered in front of Casa Bendita this afternoon while their mighty owners drank tea and listened to the songs of Russian soprano Mme. Nina Koshetz. Mrs. Henry Phipps, the dowager of this tremendously wealthy clan, and her daughter, Mrs. Frederick E. Guest, were at home to the most socially eligible of this colony’s satellites at Casa Bendita, the home of Mr. and Mrs. John S. Phipps. Some 200 guests attended the musical and tea party.”
No matter the paradox between avowed simplicity and actual grandeur, the Phipps family, for the most part, was perceived as distant from the era’s glitz as Old Westbury House’s gardens were from the City of Smoke’s steel mills where their fortune was made. At Palm Beach, the Phipps family’s corduroy, cotton, and garden-gloves mystique prompted the New York Daily News to report, “The Phippses and their guests are in no way to be confused with Palm Beach’s circus gentry. They come to this Gold Coast, not for the whoopie gaiety it offers, but because they find it a delightful winter home.”
Whatever the incongruities and nuances, here are scenes from the Phipps 1st and 2nd generation chronicle in Florida. Part I focuses on Henry and Annie Phipps as well as the setting-up of the Bessemer Trust Company. Part II spotlights Heamaw and Villa Artemis, Palm Beach’s first oceanfront mansions, designed in 1916 by Vizcaya architect Francis Burrall Hoffman Jr. Part III focuses on Los Incas and Casa Bendita, first described as “An expression of the Spanish style under the influence of the Italian Renaissance.”

Henry “Harry” Phipps Jr. & Anne “Annie” Shaffer Phipps
By the early 1900s, the elder Phipps had not only ushered the 2nd gen onto a larger world stage, but they had also initiated the family’s interests in Florida, instilling in their five children, Amy, John (Jay), Henry (Hal), Howard, and Helen, an appreciation for the state from the Everglades to the Florida Keys. During the early 1920s, Jay and Hal would do something unheard of as they tossed their New York residency and became Florida residents.
As a respite from their global treks, Britishness, and Long Island summers, Henry and Annie became seasonal visitors to Florida’s remote wilds. At first, there were stays at Jacksonville’s Hotel Windsor and St. Augustine’s Alcazar Hotel, followed by visits to Florida’s West Coast. Annie’s brother, Harvey L. Shaffer owned property in nearby Polk County. Shaffer was a protégé in his in-law’s steel business. Harvey also spent time with his and Annie’s parents’ John and Margaret Shaffer’s at their West Palm Beach cottage, believed to have been called Roseberry Cottage. A lifelong bachelor, Harvey also traveled with his sister and brother-in-law. He spent winters with them at Palm Beach and summers on Long Island where he often stayed with his nephew Jay and his wife Margarita at Westbury House.

During the 1890s, the Shaffers had escaped Allegheny City winters to a seasonal lakeside cottage located on South Olive Avenue in West Palm Beach, set on five acres with 300-feet of lakefront. In 1902, Annie bought the Layton Abbott Willson cottage, adjacent to the Shaffer place. The following year, Annie’s father died, followed two years later by her mother Margaret’s passing. While her brother Harvey was the executor of his father’s estate, he died in a tragic car-train accident on Long Island in 1906, leaving Annie and Henry with the South Flagler Drive property.


From Palm Beach, the family often took the Seminole south to the Royal Palm Hotel in Miami. They visited family members, including Henry’s sister Amelia Phipps Walker and his nephew Lawrence C. Phipps. As well, they spent time with some of their longtime Pittsburgh friends who lived along Biscayne Bay near where James Deering would build Vizcaya. Miami became the base for the family’s at-sea adventures to the Florida Keys.



From the Everglades to Inverness
Henry, Annie, the children, and staff went from Gilded Age New York and Flagler’ Florida to Great Britain aboard the era’s luxury liners during the Americanization of Great Britain, or “the invasion of American millionaires,” as coined by London’s Fleet Street. They first housed at Knebworth Castle during the early 1890s, Lord Lytton’s (Sir Edward Bulwer-Lytton) citadel. Lytton’s verse-novel Lucille was reported to be the first gift Henry Phipps gave his wife when they were first engaged to be married.


With Henry and Annie’s near every breath reported by London’s ever curious tabloids who labeled them as “distinguished strangers,” their children’s marriages made for a week’s worth of media melees. In 1903, it was Jay’s marriage to Margarita Celia Grace, daughter of international businessman Michael Paul Grace, an Irishman turned American who made England’s historic Battle Abbey his home for almost twenty years.
The following year, daughter Helen’s vows with Bradley Martin and castle reception were detailed. In 1905, the Phipps family added a touch of British upper crust when Amy married the Hon. Frederick “Freddie” Edward Guest, a cousin of Winston Churchill’s.







Just as Jay and Margarita were moving into Westbury House, their Long Island estate designed by British architect George Crawley, brother Hal’s engagement to Gladys Livingston Mills was announced. Gladys’ uncle Whitelaw Reid was the American ambassador to the Court of St. James. Her twin sister Beatrice Mills would become Lady Granard, wife of the 8th Earl of Granard. A longtime singleton, their youngest son Howard was the last to wed, marrying Harriet Price in 1931, settling in nearby Gulf Stream.

Having built several distinctive skyscrapers and buildings in Greater Pittsburgh, including the Bessemer Building, Henry Phipps was irate when a tenant, the Fulton Café located in the Phipps-owned Fulton Building, was denied a liquor license in 1909. The New York Times reported Phipps said, “Pittsburgh shall not again receive one penny of my money for playgrounds, conservatories, etc.”



Entre Nous: The Bessemer Trust Company
Following the reported $50 million windfall from the US Steel merger, Henry and Anne Phipps structured their estates to be equally shared by their five children. In a letter to each of them, Henry Phipps mapped how his legacy would be distributed and the principles fostering his “Family Plan” that evolved into the Bessemer Trust Company, state chartered in New Jersey in July 1907. Once described as “An intricate maze of trusts, corporations, subsidiaries, and investments,” today’s Bessemer Trust manages 13,000 trusts with more than $100 billion in assets for 2,500 client relationships, according to the company’s website.
Newspaper editorials termed his legacy “Henry’s Way,” suggesting other millionaires might benefit by following Henry Phipps’ lead to avoid court battles between their children and deflect inheritance taxes. While the two Phipps daughters, Amy and Helen, each held one-fifth shares, his three sons, Howard, Hal, and Jay, would manage the trust. As the oldest son and a Harvard Law graduate, Jay Phipps headed the family’s holdings during its formative years while Hal and Howard were often titled vice-presidents.

Thus, a thousand newspaper reports from 1910 until 1912 headlined that his assets went solely to the sons when for the most part they were placed in a single trust, evenly split among his children. By then, the family had formed various enterprises and companies, such as Bessemer Securities and the Bessemer Investment Company, as well as the Potomac Corporation and the Delaware Securities Corporation.
In 1924, the Bessemer Securities Corporation, a Delaware-based company was formed. All these entities were organized to “solely benefit Phipps family members (direct descendants of Henry Phipps) and charitable trusts established by those family members.”



Julian Field, longtime managing director of Bessemer Properties, told the Palm Beach Post in a 1970s interview, “By the 1940s, the family’s trust was the single largest landowner in Florida.” At that time, the Phipps name was synonymous with the development of Palm Beach, Gulf Stream, and Miami, in addition to owning tracts in Martin/ St. Lucie counties and large patches of northwest Florida plantation lands.
Although they had developed extensive residential and commercial ventures in Pittsburgh, New York, and Chicago, it would be during Florida’s early 20th-century Golden Age when the family’s legacy flourished, especially at Palm Beach, becoming known to some as “Phippsburg.”

Palm Beach 1912
During the spring of 1912, when Henry Phipps paid $90,000 for 1,000-feet of Palm Beach’s prime North End oceanfront, he stated it would be for his children to build their own houses, making for the town’s earliest oceanfront mansions. The dimensions and design aesthetics for Villa Artemis, Heamaw, and Los Incas initiated what would become the resort’s calling card, bringing about Palm Beach’s extraordinary architectural history built on the pursuit of bigger and grander houses resulting in 21st-century $100 million teardowns.
Pre-World War I was still predominately a hotel resort town with residential developments underway in the Royal Park subdivision from Royal Palm Way to Worth Avenue, Poinciana Park’s Sea Streets by City Builders, and at Floral Park, built on the north side of Main Street by the Bradley brothers. Shortly before news was published that the Flagler-owned Florida East Coast Hotel had acquired a North End dairy farm with plans for an 18-hole golf course, Anne Phipps bought the ocean-to-lake parcel on the north side of it, later publicizing it as a site for a possible polo field.

As construction began on the three Phipps family’s oceanfront houses to the north, Hal, Amy and Jay Phipps, along with Jay’s father-in-law Michael P. Grace, bought considerable undeveloped Midtown tracts extending from Wells Road south to the Bradleys’ Floral Park subdivision.
With published plans to introduce “Spanish-style houses,” complementing the lakefront, Mediterranean-styled, Fashion Beaux Art shopping promenade that opened in 1917, the Phipps group platted as many as 100 lots, naming the streets Grace Trail, Seminole Avenue, and Everglade Avenue.


Bought under the name H. W. Robbins Company, Hal, Amy, and Jay formed the joint venture, acquiring and platting a 70-lot subdivision on Grace Trail, Seminole Avenue, and Everglade Avenue. H.W. Robbins managed the family’s Henry Phipps Estate real estate holdings in New York.
In 1916, the Phipps company paid $143,255 for what became a three-street ocean-block subdivision. Lot sales from 1917-1924 totaled $443,425, according to a May 1930 report of the US Court of Tax Appeals. [ John S. Phipps vs. Commissioner of the Internal Revenue Service].






By the 1930s, the Phipps family’s conglomerate was Palm Beach County’s second-largest property owner, exceeded only by the Florida East Coast Railway and Seaboard Air Line Railway companies. In addition to developing various Palm Beach subdivisions, among them, Jungle Road/El Vedado, Via Bellaria, Woodbridge Road, and the Boca Ratone Company’s Inlet Subdivision from Mediterranean Road to Indian Road, Bessemer owned large oceanfront parcels in West Palm Beach, North Palm Beach, Delray Beach, Hillsborough Beach and on Jupiter Island.


Following decades of litigation, Bessemer Properties Inc. paid $506,500 in 1937 for the last remaining tract of the former Bula Croker property, adding 9,500-feet of ocean-to-lake property along 1.75 miles of South End oceanfront to their extensive real estate portfolio. In 1948, Phipps Ocean Park was donated. The Ibis Isle development was approved in November 1953.




Beginning perhaps, as early as the 1950s, a 3rd generation Henry Phipps heir had begun publicly demanding a forensic accounting of Bessemer Trust to determine his share of the family’s opaque trust, a claim some speculated was for as much as $100 million. Everything going back to the trust’s inception was questioned, including whether Bessemer was actually a trust, a bank, or a holding company.
Was it following Florida, New York, or New Jersey guidelines? Court papers alleged that Bessemer was “rife with unholy and incestuous relationships;” there were divided loyalties. Depositions and discovery exhibits detailed each family member’s financial records. Apparently, the affair culminated in a New Jersey courtroom in 1986. With their lives now part of court pleadings, motions, and discovery, some family members shunned the press, putting up a “No Comment-Do Not Disturb” sign that for some continues into the 21st-century.



Next —
A World of Their Own, Part II:
Heamaw & Villa Artemis
