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High Style in the Gilded Age: Jessie Woolworth Donahue

Updated: Aug 26, 2022



Frank W. Woolworth
Jennie Creighton Woolworth

In the sad saga of Jessie Woolworth Donahue’s life, there is dramatic proof that money does not buy happiness, and that love does not conquer all. Born rich in 1886, the youngest of F. W. Woolworth’s three daughters, Jessie, along with her older sisters Helena and Edna, is indulged by her father, whose five-and-dime empire has made him among the richest men in the nation. Born dirt poor himself, Frank is more than ready to live the life of a capitalist plutocrat. Not so, his wife, Jennie, whom he married in 1876, and who has been known to admit that she misses the early days when there was less money and she saw more of Frank.

2 East 80th Street, Manhattan

Frank pays millions in 1898 for the family’s five-story French-Gothic chateau at Fifth Avenue and 80th Street designed by the celebrated architect Cass Gilbert. Whenever he returns to the ornate mansion from one of his buying trips, he showers his girls with wonderful gifts. Nothing is too good for his daughters, for whom he has high hopes that they will marry well, even setting his sights on European royalty. In this respect, Jessie will disappoint, but she is the daughter who will have a significant role in the F.W. Woolworth Company, sitting on the board and watching over the family finances.

The Original Winfield Hall

With his fortune ballooning in 1898, Woolworth buys Winfield Hall, a magnificent summer home in Glen Cove, where Jessie accustoms herself to luxurious country living. The three-story mansion looks out on Long Island Sound and boasts all the amenities of her city home, plus a golf course, a magnificent rose garden, a greenhouse and more. (When it burns to the ground in 1916, he rebuilds, bigger and better.)

1907 Rolls Royce

In those early years of the new century, Jessie matures into a very entitled young woman. According to the family biographer, she attends “the finest girls’ schools in the East and often appears in public attired like a regal princess, dressed in her stunning fashions and opulent jewelry, wrapped in sable coats and chauffeured about town in her own Rolls Royce…”

James Paul Donahue

After Helena Woolworth marries a former district attorney in 1904 and Edna marries Franklyn Laws Hutton, a partner in the banking firm E.F. Hutton, in 1907, only Jessie remains to fulfill her father’s dreams of a royal son-in-law. But when the 27-year-old Jessie meets a handsome young Irish-American charmer at a New York City skating rink, those hopes are dashed. Jessie falls hard for James Donahue’s playboy glamour, so different from the dullards she thinks her sisters have chosen. Though James has all the manners of a gentleman and does, in fact, have a rich family, his social standing is nowhere near what Frank Woolworth is prepared to accept for his daughter. James is one of 11 children of Patrick Donahue, whose fortune derives from a fat-rendering factory at the foot of West 39th Street. His low social rank and the smelly source of the family wealth have Frank Woolworth pleading with Jessie not to marry him--to no avail.

Nos. 2, 4 and 6 East 80th Street Homes of Helena, Edna & Jessie

On February 1, 1912, the day that Jessie and James marry in the Woolworths’ Fifth Avenue townhouse, Jessie’s father spends the morning on his office couch weeping uncontrollably. When the hour arrives, he gives the bride away with a heavy heart. Jessie, dressed in a white satin gown with a lace trimmed court train, carries a bouquet of lilies of the valley and wears the groom’s wedding present, a diamond and sapphire brooch...bought with her money. Jessie gives James a wedding present of $5 million. Her forgiving father gives the couple a townhouse near his own, which he has also done for her sisters so that the Woolworth daughters and their husbands monopolize the neighborhood.

Jessie, James, Woody and James Jr.

By all accounts, Jessie is a rather cold, hands-off mother to her two sons, Woolworth (mercifully called Wooly), born in 1913, and James Jr., known as Jimmy, in 1915. For the first 10 years of their marriage, the Donahues spend much of their time traveling abroad, relying on governesses to take charge of the children. Jessie seems to regard her offspring as decorative adjuncts, along with her jewels, her houses, her Rolls-Royces and her private railroad carriage. She is known to favor Jimmy, a child of exceptional beauty.

Barbara Woolworth Hutton, 10 years old

The massive fortune and a lavish lifestyle acquired by the rags-to-riches Frank Woolworth do not guarantee protection from heartache. When Jessie’s sister Edna Hutton, aged 33, commits suicide in May 1917 by swallowing a vial of strchnine crystals, her 6-year-old daughter Barbara is the one who discovers the body. Her devastated grandfather, Frank, steps in for Barbara’s philandering father, giving Barbara a home in the opulent Winfield Hall and acting as her fond protector. Barbara and her cousin Jimmy have always been kindred souls, with a wild streak, and their bond is strengthened when Barbara is so often with her cousins after her mother’s death. Then, on June 7, 1918, Frank feels he must petition the courts to declare his wife Jennie incompetent due to what her doctor terms “a pre-senile condition.” Toward the end of 1918, Frank Woolworth’s own health begins to fail and at his death in 1919 Barbara loses a beloved grandfather but will inherit doubly from Hutton wealth as well as her mother’s share of the Woolworth fortune.

Cousins Jimmy Donahue and Barbara Hutton at a Party

As adults, Barbara and Cousin Jimmy will always have the wherewithal to lead reckless lives, hitting cafe society’s wild international haunts, drinking, dancing and pursuing men. Beautiful men are Jimmy’s obvious preference and, in Barbara’s case, the pursuit leads to an astonishing seven marriages. Among her bridegrooms are a count, a baron, a prince and Cary Grant, whose wedding to the notorious “poor little rich girl” is mocked as “cash and Cary.”

Jessie Woolworth Donahue

Meanwhile, Jessie’s marriage to James is proving as troubled as her father had predicted. After a two-month bridal trip, the restless James resumes has resumed his playboy ways, gambling, drinking and cruising cafe society hotspots for more seductive companions than his wife, who has lost the youthful elan that had briefly attracted him on the roller rink. Jessie is aging into a rather graceless matron. Rather than admit that her father was right to oppose her marriage to James, Jessie decides to use her enormous wealth as a counter-force against her husband’s disgraceful behavior--an effort that backfires when her ostentatious spending leads to criticism and social snubs.

Mr. Bojangles

Jessie’s two sons, with childhood behind them, add to her troubles. Wooly less so than Jimmy, though there are raised eyebrows over Wooly’s womanizing, his lavish and costly African safari that lasts a year and involves more than 30 elephants, and his acquisition of a private hunting lodge known as “Riverhead.” He fills the lodge, which is located on Long Island in Manorville--later a Riverhead Town Rod and Gun Club--with his trophies. Still, it is the favored Jimmy who causes Jessie the most worry as he is asked to leave one school after another in the 20s and early 30s. His refusal to abide by any restrictions whatsoever leads to his expulsion from the Harvey School, the Hun School and eventually from Choate. Among his many transgressions there is an unauthorized escape from his dorm to New York City on a whim, to take dance lessons from the sensational black dancer Mr. Bojangles.

The Brooklyn Daily Eagle, Oct. 3, 1925

Jessie is also struggling to set some limits on her husband’s gambling. As his losses mount, she tries mightily to enforce nightly limits, but without success, and his constant need for more money seems to have been behind a very bizarre family episode. On October 1, 1925, Jessie is preparing for a formal evening out in New York, when she discovers that her jewel drawer has been emptied of nearly $700,000 worth of jewelry (more than $6 million today). The New York Times describes it as “the greatest jewelry robbery in the history of the city.” And the Brooklyn Eagle reports that a distraught Jessie had gone into seclusion. For several years afterward, the sensational Donahue Jewel Heist continues to fascinate the press as a long, tangled investigation repeatedly fails to nail the culprit. Long afterward, it is James’s son Wooly who reveals what many have suspected: it was his father, James Sr. who had stolen the jewels in his desperate effort to put a dent in his debts without asking Jessie to cover them.

Wooldon Manor

In 1920, eager to enter the social swim in Southampton, and also, no doubt, to keep the marital fires burning by offering James another magnificent residence to show off, Jessie uses her fortune to buy a huge, 26-room Tudor-style mansion on 16 oceanfront acres in Southampton. She immediately begins remodeling the mansion,which she calls Wooldon Manor, and furnishing it in the most extravagant fashion. Husband James is particularly thrilled by the beach house with its lounges, bar, dressing rooms and indoor swimming pool. By 1927, Jessie has spent $3 million on the summer residence but failed to crack the elite beach club next door. Rumors circulate that the reason given for the club’s snub was that Jessie’s vast inheritance was from a member of the scorned merchant class. One wonders if they knew about the fat-rendering factory. Possibly it was just easier to fall back on class snobbery than to get into James’s reputation for depraved carousing.

Cielito Lindo Palm Beach

Disappointed by the beach club rejection, and beginning to realize that her extravagance is not impressing Southampton society, Jessie looks toward Florida as a better place to make her social mark. In 1927, she conceives a magnificent Palm Beach fantasy palace, which she will call Cielito Lindo (a bit of heaven), and which will rival the fabulous Mar-a-Lago in its Mediterranean-style splendor. With her eye on the 1928 Palm Beach social season, she rides herd on building crews to work with record speed on the 122-bedroom residence and its grounds that will boast formal gardens, a tea pavilion, orange groves, tennis courts and a three-story tower. Designed for royal-scale entertaining, Cielito Lindo formally opens on April 20, 1928, with a proud Jessie presiding over one of the largest private affairs of the season at her new estate. It is declared one of the five largest and most notable homes ever built in Palm Beach.To build paradise had taken less than a year.

Colonel Bradley’s

Jessie is able to revel briefly in the success of her party, putting aside her son Jimmy’s refusal to integrate into the boarding school elite, as she had hoped, and deluding herself that the magnificent Cielito Lindo will amuse her wayward husband and keep him close. He seems happy at first in Palm Beach, where he can pass for old wealth, a world away from the fat-rendering factory. But it is not in his nature to settle for a life without risk and excitement. Deprived of such stimulants he is subject to bouts of depression. In Palm Beach he finds the outlet he needs in the gambling rooms of Colonel Bradley’s Beach Club, where his losses are staggering. While Jessie fights to control the outflow, she abandons the fight to control Jimmy’s education. After Choate there is no more formal schooling for Jimmy, who is free to follow in the footsteps of his undisciplined father.

New York Times, April 24, 1931

On April 13, 1931, on her return from Palm Beach, Jessie Donahue is admitted to the private Harbor Sanatorium at 667 Madison Avenue suffering from a nervous breakdown.The extent to which her husband’s massive debts and depressed state have driven her over the brink is not known, but that same week, James Sr. draws up a new will. The following week he invites two friends to join him and both sons for lunch at 6 East 80th Street. Excusing himself from a card game after the meal, he takes six tablets of bichloride of mercury from the medicine cabinet and staggers back to his guests, violently ill. It is an act of virtual self-destruction following years of alcohol and drug abuse. The efforts of his sons to save him are futile and he is taken to the Harbor hospital, where Jessie is wheeled in from another ward to witness her husband’s death.

NYT April 30, 1941

Jessie rallies after James’s death. He has plundered her fortune, prompting her to make a few gestures at scaling down, though she remains a fabulously wealthy woman. She now shares a massive Fifth Avenue duplex with Jimmy, who lives large and dangerously. He is in his element in all the bastions of excess and indulgence favored by Cafe Society, often accompanied by his cousin Barbara. When the U.S. joins the fight in WWII, Jimmy is drafted into the Army, from which he is eventually dishonorably discharged after making suggestive comments to an officer at Fort Dix. Jessie will always welcome him back, though he will always bring trouble. She no longer has any interest in Wooldon Manor, her showplace in Southampton, which she sold in auction in 1937 for $137,000. It survives the 1938 hurricane but in 1941, when gardeners and butlers are all off to war and belts are tightened, the residence is razed, leaving only James Donahue’s much-loved pool house intact.

Jimmy and the Duchess

The Duke and Duchess of Windsor, refugees from wartime Europe, arrive in Palm Beach in April 1941 with plans to visit the opulent Cielito Lindo with its fabled historic hand-carved Hogarth Library, which Jessie had purchased in London in 1924. Jessie is thrilled to host the famous quasi-royals; the Duke takes a shine to Wooly, and the Duchess, restless and bored, is captivated by Jimmy’s jokes and uninhibited behavior. Soon she is relying on him to cheer up the gloomy Duke, and then their relationship takes a scandalous turn. Society is amused and shocked when Jimmy, who is 34, and the 54-year-old Duchess of Windsor form a bizarre love triangle with the Duke. It may be a scandal but no one is more thrilled than Jessie, who shamelessly puts a nice chunk of her fortune at the Windsors’ disposal. There are jewels for the Duchess, and lavish entertainments and excursions for the trio, which is a foursome when she comes along. A close personal tie to the Windsors is a social coup of the first order.


After four years and three months of each other’s company, the Windsors and Jimmy are beginning to tire of each other, and when Jimmy kicks the Duchess in the shin over a trivial matter, drawing blood, the affair ends abruptly and completely. Jimmy and his mother pick up where they left off, he to provide scandalous grist for the gossip mill, and Jessie to struggle to reclaim the social spotlight without the Windsors. She summers in Newport beginning in 1945, but sells her house there and in 1956 buys the manor house known as Claverack in Southampton. Built in 1892 on Halsey Nick Lane for Brigadier General Thomas H. Barber, it was modeled on the 1764 van Rensselaer manor house on the Hudson. It is her last mansion and to furnish its 30 rooms with the contents of 100 rooms, now in storage, requires some hard choices.

The Woolworth Mausoleum

On September 23, 1966, Jimmy is found dead in his bed at 834 Fifth Avenue. He has died after yet another night of too much alcohol and too much Seconal, and it falls on Wooly’s wife Mary to break the news to Jessie that her favorite son is dead. “This is the worst thing that can happen to me,” is Jessie’s quiet reply. Twenty-seven limousines follow Jimmy’s coffin from the funeral mass to Woodlawn Cemetery. At the front of the cortege are leading members of New York high society--Astors and Vanderbilts, paying tribute to vast wealth. Toward the back are his friends and lovers who knew a different Jimmy. Five years later, in 1971, when Jessie dies at the age of 84, she will join Jimmy in the fanciful Woolworth family mausoleum in Woodlawn Cemetery designed by John Russell Pope. When her will is opened, it demonstrates her mastery over at least one aspect of her life: her personal and financial assets. There are no blanket bequests. Instead, there is a long list of very specific and carefully chosen bequests disposing of her vast fortune and her many possessions down to a single diamond brooch for her son Wooly’s wife.

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2 Kommentare

Came across this when trying to identify who "Mrs. James P. Donahue" might be in an art dealers' archives I'm working on - thank you for this fascinating essay!

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Pius Twelvetrees
Pius Twelvetrees
23. März 2021

The woman shown in photo third from bottom is not Wallis Simpson, the Duchess of Windsor. The photo caption is not accurate.

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