25. Winnaretta Singer: The Sewing Heiress
Born in 1865 in Yonkers, New York, Winnaretta Singer was one of the heiresses to the massive Singer sewing fortune. In fact, the family fortune was so massive that even though Winnaretta was the 20th of an incredible 24 children for her father Isaac Singer, she still had a million-dollar inheritance.
This was too enticing for any self-respecting old noble family to ignore, but any amorous husband who came in contact with Singer learned to regret it.
Winnaretta Singer (1865-1943), Wikimedia Commons
26. She Had An Unlucky Childhood
Singer’s young life was tragic and tumultuous, with a childhood spent pinging between European countries before her father’s passing when she was 10 years old. Unfortunately, when her mother remarried, it was to a brute of a man who abused Singer, spurring the young girl to seize control of her inheritance the moment she was of age and go live on her own.
It wasn’t long before she was in a new kind of trouble.
27. She Became A Countess
Despite her relative freedom and objective wealth, at 22 years old Winnaretta found herself married to the French nobleman Count Louis de Scey-Montbeliard, a man who surely enjoyed the prospect of her family money. However, Count Louis likely never enjoyed the prospect of Winnaretta Singer herself: On their wedding night, he found out her secret.
Winnaretta Singer, Wikimedia Commons
28. She Threatened Her Husband
Although people within Singer’s inner circle knew that she was a lesbian, Count Louis himself seemed to have missed this piece of gossip, and he learned about it the hard way. On the night of their marriage, when the two were alone together, Singer reportedly climbed onto an armoire and threatened to kill the Count if he so much as touched her.
Somehow though, Singer managed to make marriage work for her. Just not this one.
John Singer Sargent (1856–1925), Wikimedia Commons
29. She Found The One
After five years of this, the Count and Singer had the marriage annulled by the Catholic Church—having a much easier time of it than Boni and Anna Gould, not the least because there was little evidence of intimate relations. In 1893, the 28-year-old Winnaretta then married another noble, the 59-year-old Prince Edmond de Polignac, in a lavender marriage that suited the lesbian Singer and the gay Polignac just fine.
Of course, this only made it easier for Singer to stir up drama.
30. She Was A Heartbreaker
The leading women of Singer’s day seemed to find her irresistible, and over the years she carried on affairs with the likes of the beautiful painter Romaine Brooks as well as King Edward VII’s rumored illegitimate daughter Olga de Meyer. These women’s husband sometimes also found her infuriating: One scorned lover reportedly turned up outside Singer’s Venetian palazzo and ordered her, "If you are half the man I think you are, you will come out here and fight me”.
But for every romping story like Winnaretta Singer’s, the dollar princesses have ten more tragedies—even when they have loving marriages.
Unknown authorUnknown author, Wikimedia Commons
31. Mary Curzon: The Perfect Bride
Mary Curzon is one of the most famous dollar princess “success” stories, but her fate post-marriage was as tragic as they come. Born in 1870 in Chicago as Mary Leiter, her father was an incredibly successful merchant, and Mary herself earned a reputation for being as well-bred and educated as she was beautiful.
When she caught a husband, then, he was a very big fish indeed.
Alexandre Cabanel, Wikimedia Commons
32. She Fell In Love With A Future Baron
Soon after being introduced to London society, the 20-year-old Mary met the 35-year-old George Curzon, a member of parliament and the heir to the Barony of Scarsdale. Unlike so many other dollar princesses, Mary was drawn more to George for his political aspirations than for his title, and their marriage in 1895 was a love match. It would also rocket them both to international power.
George Grantham Bain Collection (Library of Congress), Wikimedia Commons
33. She Charmed Everyone
Like Jennie Jerome, Mary was one of the most charming, diplomatic wives around, and when her new husband won re-election to Parliament soon after their wedding, many credited his bride’s sweet smiles for the feat. This upward trajectory continued, and a handful of years later George became Viceroy of India, with Mary becoming Vicereine, the highest official title in the Indian Empire for a woman.
Mary seemed to have it all, which is when fate came and snatched it away.
![Lord Curzon-Elephant [sic] procession to Sanchi Tope.](https://www.factinate.com/storage/app/media/factinate/2026/4/24/1777023286cb2d85a6bb4595c07e4f29ddb0f7ff355fb3e9d6.jpg)
Lala Deen Dayal, Wikimedia Commons
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34. She Couldn’t Give Him A Son
In truth, something had been missing from the Curzon marriage for a while: A son and heir that George desperately wanted. Instead, Mary gave birth to a succession of three girls, the last of whom was born during her time as Vicereine in 1904. And though she tried to get pregnant again right after, she suffered a bitter miscarriage.
Weighed down by her “failure” as well as her endless political duties, Mary’s health grew frail. Until the day it snapped.
Bain News Service, publisher, Wikimedia Commons
35. She Would Not Give Up
Mary was so ill that doctors told her husband to prepare to say goodbye—but then, she made a miraculous recovery. That's when he made a chilling choice. Once more putting his work above everything else, even the woman he loved, he took his post back up in India and left Mary to convalesce alone. And even as sick as she was, she took her own wifely duties seriously.
When she was barely able to move around, and only with help, she wrote to George and told him she would join him in India shortly. And surprisingly, she did—but that didn't mean the nightmare was over.
William Logsdail, Wikimedia Commons
36. She Perished Young
In the summer of 1906, Mary Curzon’s body gave out. An illness and awful cough that “shook [her] bones to pieces” took over, and she wrote to her brother, “I sometimes fear and feel I shall never be well again”. That July, she suffered a fatal heart attack at just 36 years old, proving that even when a dollar princess’s marriage goes well, it can still go so wrong.
While Mary helped shape British politics for years to come, the next dollar princess helped shape an American dynasty.
Unknown. Bourne&Shepherd, Dec. 1902, Wikimedia Commons
37. Consuelo Yznaga: The Best Friend
Consuelo Yznaga isn’t well known today, but as her story and scandal go on, you’ll see just how embedded she is in American history…at least, in its backdoor bedroom dealings. Born in New York City in 1853, Yznaga hailed from Cuban nobility and a long line of plantation owners. As such, she grew up with the future elite of New York society, what novelist Edith Wharton would go on to describe as the “Buccaneers.”
In fact, her childhood best friend Alva Smith married William Vanderbilt, scion of the American Vanderbilt family. But Yznaga’s own marital accomplishments were nothing to sneeze at.
Unknown photographer, Wikimedia Commons
38. She Was A Future Countess
While Yznaga’s friend Alva kept her money stateside, she went the dollar princess route, marrying George Montagu, the Viscount Mandeville, in 1875. Since George was the future Duke of Manchester, it was only fitting that Yznaga brought with her an eye-popping dowry worth multiple millions when converted into today’s money.
But all the money in the world couldn’t save her now.
The Sketch, Vol. XXXIII, No. 426, March 27, 1901, page 375, Wikimedia Commons
39. She Married Into A Nightmare
Consuelo Yznaga had been sold a fairy tale, but almost as soon as she settled into her new European estates, she realized something had gone horribly wrong. Her husband might have been a future duke, but he was also an utter brute, and in less than a decade he had squandered all the money she’d brought in on gambling and mistresses.
The Duke was so far gone, Yznaga’s father in-law banished the couple to Ireland for years to get him under control. But when Yznaga emerged back into society, it didn’t get much better.
40. She Betrayed Her Best Friend
Yznaga’s terrible husband passed in 1892, leaving her free to do what she wanted…which wasn’t a good thing. Around the same time, Alva Vanderbilt shocked society by demanding a divorce from her husband William. Rumors flew as to the reason why—but no one guessed the sickening reason for the split. According to some whispers from those who knew the couple, William Vanderbilt hadn't just cheated on his wife—he'd cheated with her best friend, Consuelo Yznaga.
Perhaps the most poignant part? Alva had actually named her own daughter Consuelo after her traitorous friend, who she’d also made the girl’s godmother. But this goddaughter had possibly the worst time as a dollar princess.
![Portrait of Consuelo Yznaga, Duchess of Manchester [2] (1853-1909), wife of George Montagu, 8th Duke of Manchester (1853-1892).](https://www.factinate.com/storage/app/media/factinate/2026/4/24/1777015331c4ec5e60667c0bbc8dab8ef87fd6450a840382b7.jpg)
John Singer Sargent, Wikimedia Commons
41. Consuelo Vanderbilt: The Pitiful Princess
From the moment of Consuelo Vanderbilt’s birth in 1877, Alva was determined that her daughter make an aristocratic European match just like her namesake. Accordingly, Alva forced the girl to wear a steel rod from a young age to perfect her posture, and would whip her with a riding crop at any sign of misbehavior.
The Vanderbilt matriarch was open and unapologetic about her control; when Consuelo once protested, her mother retorted, “ do the thinking, you do as you are told”. It would be her doom.
USA Library of Congress Bain collection, Wikimedia Commons
42. She Was Stunning
Like her predecessor Jennie Jerome, Consuelo won both the family and genetic lottery, being both unimaginably wealthy and unimaginably beautiful. Peter Pan playwright James Barrie wrote, "I would stand all day in the street to see Consuelo Marlborough get into her carriage,” and men went wild for her "piquante oval face” and “long slender neck”.
By the time Consuelo reached maturity, she was the embodiment of the “slim, tight look” that characterized women during the Edwardian era. And her mother knew this all too well.
http://www.americanprincesses.com/example3.htm, Wikimedia Commons
43. Her Mother Had One Dream For Her
By the time Consuelo became of marriageable age, Alva was sure she could win her daughter one of the biggest catches in Europe, namely Charles Spencer-Churchill, the 9th Duke of Marlborough, who came from an illustrious family and was also the cousin of Winston Churchill. There was just one thing Alva hadn’t counted on.
William van der Weyde, Wikimedia Commons
44. She Was In Love With Someone Else
Consuelo was singularly uninterested in the Duke, title or not—because she was utterly in love with the socialite Winthrop Rutherfurd, a man 15 years her senior who possessed less than half the possibilities of a Duke of Marlborough. And when it came to keeping Rutherfurd, the normally compliant Consuelo got downright rebellious.
Lafayette L2115a, Wikimedia Commons
45. She Put Her Foot Down
Instead of caving to Alva’s demands, Consuelo planned to elope with Rutherfurd, thereby ending the marriage negotiations with the Duke once and for all. Sadly, her domineering mother was more than ready for her. When Alva got wind of Consuelo’s plans, she locked her daughter in her room, all while threatening to harm Rutherfurd and force Consuelo down the aisle.
When that didn’t work, Alva upped her machinations.
![Mrs. O.H.P. [Alva] Belmont](https://www.factinate.com/storage/app/media/factinate/2026/4/24/1777020673ed16d8cbf00b51d289e71fa320e8f52782fd47a1._O)
Adam Cuerden, Wikimedia Commons
46. Her Mother Played Dirty
As Consuelo staunchly refused to marry anyone but Winthrop Rutherfurd, Alva began getting extremely “ill,” a “sickness” apparently brought on by her daughter’s stubborn refusal to listen. The more Consuelo stood her ground, the closer Alva got to death’s door…until the girl, fearful she really was killing her mother, agreed to the wedding at last.
At that point, Alva suddenly made a full recovery. Enough to witness one of the worst days of her daughter’s life.
Stadler Photographing Co., New York-Chicago, Wikimedia Commons
47. She Bawled At The Altar
Consuelo Vanderbilt’s wedding to the Duke of Marlborough was the talk of society, but so too was her strange behavior on her “special day”. Reportedly, Consuelo spent her time at the altar uncontrollably weeping behind her veil. Meanwhile, the Duke collected $2.5 million, nearly $100 million in today’s money, as a marriage settlement that would inject new life into his dilapidated estates.
It was the beginning of something truly awful.
Carolus-Duran, Wikimedia Commons
48. Her Husband Made A Terrible Confession
It only took until the honeymoon for Consuelo to realize the full impact of her mistake. Not only was the Duke a relatively shallow man, he was also utterly dismissive of her. Then he made a series of chilling confessions. First, he admitted he’d only married her to “save Blenheim,” his ancestral home, and then informed her that he, too, was completely in love with someone else, and didn’t intend to romance her beyond producing an heir.
Philip Tennyson Cole (1862–1939), Wikimedia Commons
49. She Couldn’t Let Her Old Flame Go
Miserable with the Duke even after giving him a son, Consuelo rekindled her relationship with Winthrop Rutherfurd just a few years later. Eventually, she confessed to her husband that she still wanted to elope with Rutherfurd, and there were even scandalous whispers that her second son belonged to him, not the Duke.
But even when the Duke reluctantly agreed to a possible split and elopement, no happy ending was in sight.
John Singer Sargent, Wikimedia Commons
50. Her Love Rejected Her
In 1900, Consuelo went to London to sit down and discuss elopement with Rutherfurd—only to receive the shocking news that he didn’t want to marry her. In the desperate aftermath, and while her husband was away, Consuelo began an affair with the Duke’s cousin, Reginald Fellowes, and may have done the same with the artist Paul Cesar Helleu.
Clearly, Consuelo now wanted out no matter what it took, and soon both spouses couldn’t deny it.
51. Her Mother Admitted She Was Wrong
Before long, the Duke and his dollar princess were barely on speaking terms, much less intimate ones, and they separated in 1906, officially divorcing in 1921. In a too-little-too-late moment of vindication, even Consuelo’s own mother Alva admitted during the court proceedings that the marriage was a mistake, confessing, “I forced my daughter to marry the Duke”.
But the end of Consuelo’s marriage wasn’t quite the end of her tragedy.
52. She Got Something Of A Happy Ending
Consuelo Vanderbilt, for all her looks and wealth, was nearly endlessly unlucky in love. At one point near the end of her marriage, she planned to elope again, this time with the already married Marquess of Londonderry, only for it to also go up in smoke.
Eventually, Consuelo did find happiness when she married Jacques Balsan, an early lover of Coco Chanel; she remained married to him until his passing in 1956. When Consuelo herself passed in 1964, many saw it as the true end of a not-so-gilded era.
Interim Archives, Getty Images
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