High Style in the Gilded Age: Jessie Woolworth Donahue



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.