In the Gilded Age, Caroline Astor ruled New York. Born Caroline Schermerhorn, she was already a member of one of the oldest families in the metropolis before she married into the obscenely wealthy Astor family. Soon enough her lavish parties, rigid etiquette, and clique of mean-girl socialites had turned Caroline into the gatekeeper of the New York Elite. And she didn’t become the Mrs. Astor by playing nice.
1. She Came From Big Money
They say anyone can make it in America, but Caroline Astor was not just anyone. Born in 1830 to the Schermerhorn clan, she could trace her ancestors all the way back to the founding of New York City, a claim many would beg, borrow, and steal to make. Moreover, all that time in America had produced a mountain of wealth; her father Abraham was worth half a million dollars when she was born. And with all that money came big plans for little Lina.
2. She Had The Wedding Of The Year
After an extravagant childhood, Caroline came out into the world with a bang. After learning the best manners money could buy, she married William Backhouse Astor, Jr. at the age of 23. The middle son of the Astor real estate and fur-trading empire, William had a lot of money to throw around, and it was one of the society weddings of the season.
But there is one thing about their nuptials most people don’t know.
3. She Married Down
Today, the Astor family is a towering dynasty, and old New York and the Gilded Age are practically synonymous with the clan. But believe it or not, it was Caroline who was stooping when she married William, not the other way around. As one of the oldest families in New York, the Schermerhorns had much more clout than the upstart Astors. And Caroline made sure her husband knew it.
4. She Was Ambitious
Caroline had been brought up to be unfailingly polite and prim, but the young wife was hiding a dark secret. She quite liked lording her status over people, and after giving William five children, she set about distinguishing herself from anyone beneath her in society. She became infamous as a New York city gatekeeper…and with this "job" came a strange obsession.
5. She Was A Queen Bee
At the time, scores of people were rushing into New York to make a name for themselves, and Caroline thought it was her job to perform quality control. As a result, she started fixating on etiquette rules as a test for who was worthy of entering her company. She also began throwing lavish parties, exquisite teas, and impeccable receptions at her home, making sure only to invite guests that were of her social standing.
And there was one guest in particular she never failed to invite.
6. She Had A Clique
At the height of her party planning and social climbing, Caroline had one bona fide partner in crime: The lawyer and man about town Ward McAllister. Incredibly enough, McAllister was even more obsessed with social standings than Caroline, and together the mean-girl duo took this obsession with cliques to a new level. Like, a particularly terrifying new level.
7. She Loved Excluding People
In order to flex their power, the duo came up with a devious plot. McAllister made an index of "The Four Hundred"—as in, the mere 400 hundred people who he and Caroline considered the cream of New York society. In fact, Caroline had such a hand in this list that the (false) rumor went around that they decided on that number because it was the number of people she could fit into her ballroom.
The list was basically the Gilded Age version of a burn book, only, in this case, being excluded was the burn. And guess what? It worked.
8. People Were Obsessed With Her Smell
Before long, Caroline Astor had more than made a name for herself; she was a downright sensation. Gossip hounds begged to know what she had worn to soirées, and sharp-nosed guests feverishly noted that her perfume was a "sweet odor somewhat like wild lavender and garden roses mixed". Many even rumored that one of her bodices used to belong to Marie Antoinette.
From the outside, it seemed like Astor had the perfect life. But if you looked closely, the cracks were starting to show.
9. She Was In A Sham Marriage
Caroline’s marriage to William Astor had been good for both of them, giving him prestige and her even more money. But they were hiding something from society. Even with their five children, it was a supremely chilly marriage, mostly because William preferred lolling about on yachts to doing pretty much anything with his wife. This took a toll on Caroline.
10. She Was Desperate For Attention
Although she always put on a perfect smile for her adoring public, Caroline Astor may very well have been wilting inside. Indeed, many historians believe that it was William’s neglect that pushed Caroline into her frenzied social life, filling her romantic void with the friends and frenemies of the ballroom. Oh, but William had something to say about that too.
11. Her Husband Didn’t Understand Her
Not content to just snub his wife, William could be explicitly cruel to Caroline when he wanted, too. Whenever he managed to come home, he expected his place to be his own quiet sanctuary, and Caroline’s many gatherings often frustrated him. So what would he do? Break up the party, send the orchestra home, and order his children to bed, naturally.
Still, Caroline was one smart cookie, and she knew exactly how to turn the situation to her advantage.
12. She Manipulated Her Spouse
Caroline quickly learned how to deal with her recalcitrant husband. Namely, she nipped William’s disruptive arrivals back home in the bud. In fact, they grew so scarce that people began to whisper that Caroline now purposely kept him out at his various clubs so she could curb his outbursts. Still, even she couldn’t handle her next high society rival.
13. She Had A Huge Rival
At the time Caroline was reigning supreme, another power was ascending to challenge her authority: New money. Specifically, the new money of the Vanderbilt family. See, this now elite family was tres nouveau riche at the time, and Caroline and her posse considered them coarse and not fit for company. Which maybe explains the devasting insult she dealt them.
14. She Played An Infamous Power Game
By the 1880s, the Vanderbilts were growing so wealthy from their railroad empire, even Caroline couldn’t pretend they didn’t exist. Instead, she snubbed them in the worst way possible. She pointedly refused to call on Alva Vanderbilt, one of the leading Vanderbilt wives of the day, thereby assuring she could never come to any of her highly sought-after social events. Oh, but Alva got her back, right in her weak spot.
15. She Played Favorites
Of all Caroline’s children, her daughter Carrie and her baby John "Jack" Jacob Astor were the most lauded by society—and Caroline liked to show her daughter off especially. After all, one newspaper had dubbed Carrie the "beauty of the house of Astor". Caroline’s vanity about her daughter, however, was also a gap in her armor…one Alva jumped on.
16. She Got A Cruel Snub
While feuding with the Vanderbilts, Caroline was also busy trying to get Carrie out into society. So when the Alva Vanderbilt held a housewarming costume party in the family’s new, massive manor, the Astor matriarch was shocked that her daughter Carrie didn’t get an invite to participate in some of the evening’s activities. After all, Alva had never "officially" met Caroline Astor. It had far-reaching consequences.
17. She Made A Public Surrender
Faced with her daughter’s potential loss of status, Mrs. Caroline Astor broke down. At long last, she had to actually pay a visit to the Vanderbilt home so Alva could drop the pretense and actually invite Carrie to her party. With the visit, the walls of high society came tumbling down: The Vanderbilts were finally with the "in" crowd. Later, Caroline admitted, "The time has come for the Vanderbilts".
Only, as it happened, this entire time Caroline Astor was ignoring the real threat to her existence…and it was coming from inside her family.
18. She Didn’t Play Nice
We already know that the Astors’ picture-perfect family life only looked that way from the outside. But the mess extended far past Caroline’s relationship with her distant husband. In reality, Caroline didn’t get along with the whole Astor family in general, particularly with her husband’s older brother John Jacob Astor III—or his wife, Charlotte Augusta Gibbes. And in 1862, things really hit the fan.
19. She Started A Trend
As a new decade came on in the 1860s, Caroline thought it was high time to show society what she was really worth. Accordingly, she and William commissioned a brand spanking new brownstone—which was a very modern and fashionable style of building at the time—at 350 Fifth Avenue, right in the heart of the posh Upper East Side. But there was one enormous problem.
20. She Was In The Middle Of A Family Feud
When Caroline moved into her new home, she had familiar neighbors: Her hated brother-in-law John Jacob III and his wife Charlotte. And familiarity definitely bred contempt in Caroline and Charlotte’s case. Huge mansions to live in or not, the close proximity put a further strain on their already tense relationship. Until, one day, Caroline got the surprise of her life.
21. She Outlived Her Enemy
In 1887, at the relatively young age of 62, Caroline’s frenemy Charlotte passed on. Sure, Caroline probably affected all the usual mourning rituals and gave nothing but her high-society best when it came to sending off her sister-in-law. And yet. There’s simply no denying Caroline was happy about the turn of events—and she had one chilling reason for her joy.
22. She Gave Herself A New Name
In the Gilded Age, your family name meant everything, and there was a huge hierarchy about naming conventions. For example, before Charlotte Gibbes passed on, she was the "Mrs. Astor," a title of great honor—after all, Charlotte was the elder wife of the elder brother of the Astor family. Meanwhile, Caroline had to be happy with being the mere "Mrs. William Astor".
Well, now that Charlotte was gone, Caroline knew the title was up for grabs and intended it for herself. In fact, she wanted it so much, she nearly destroyed the Astor family.
23. Her Nephew Challenged Her
In the days following the funeral, Caroline got alarming news. Although she was all ready to step out into society as the one and only "Mrs. Astor," her feud with Charlotte haunted her from beyond the woman’s grave. That’s because Charlotte’s beloved son William Waldorf—who knew how much his mother hated Caroline—wanted to rip the honorary title from Caroline’s greedy hands and give it to his wife Mamie. Enter: All-out war, high society style.
24. She Was A Mean Girl
Caroline Astor must have taken one look at poor Mamie and bared her teeth. After all, the girl was a full 18 years younger than Caroline, and hadn’t spent the last decade of her life playing society hostess and building up every ounce of clout she could in various balls, luncheons, and teas. In other words, Caroline immediately came up with a plan, and poor Mamie didn’t know what hit her.
25. She Crushed Her Rival
For the next months, the two sides of the family engaged in a silent feud with each other, each trying to get their pick for the Mrs. Astor to win. Except, well, Caroline was way ahead of the game. By the time William Waldorf and Mamie could even blink, she’d already carried away the trophy, and everyone recognized her as the preeminent Mrs. Astor. Which is right about when William retaliated with a stunning move.
26. She Made The Wrong Person Mad
Licking his wounds from the "Mrs. Astor" battle, Caroline’s nephew got a vicious revenge. Caroline woke up one morning in her Fifth Avenue home to find out that her new neighbor was no longer John Jacob Astor’s old house, but a construction site. That’s because William Waldorf, petty as all get out and annoyed at Caroline, had torn the house down. But it’s what he was building in its place that was the real attack.
27. Her Family Tried To Disgrace Her
As it happened, the spiteful William Waldorf wasn’t just building another stately mansion; he was building the very first and very famous Waldorf Hotel. See, at the time, respectable society people never met in public places; you simply had to be invited to someone’s private party to get into the in-crowd. He was telling Caroline exactly how he felt about her. And that wasn’t the only part of the insult.
28. Her Influence Was Under Attack
Besides shoving some nouveau riche contraption right in Caroline Astor’s face, her rebellious nephew also purposely built the Waldorf so that it towered over everything in the area, including Mrs. Astor’s own home. This, of course, was a not-so-veiled attempt to tower over Caroline’s own social influence. Yep, William fully intended Caroline to be insulted at the down-market building…and oh, she was.
29. She Had A Cutting Wit
With the Waldorf Hotel staring her right in the face, Caroline couldn’t help but be offended. And she had the perfect comeback. In a fit of sharp wit, she reportedly sniped about the "glorified tavern next door," a bon mot that had made its way all around New York City and is still infamous today. Still, Caroline Astor wasn’t just about words, she was also about actions. She planned her counter-attack very carefully.
30. She Plotted Her Revenge
In the wake of the Waldorf, Caroline teamed up with her son John "Jack" Jacob Astor IV to find a way to hit back at their relative. Their first idea was the definition of petty: They wanted to tear down their own house and build…horse stables in its place, just in case Waldorf needed a clearer picture of what Caroline thought about him. But then they hit on another idea entirely.
31. She Hit Back Where It Hurt
Faced with this expensive problem, Caroline came up with an ingenious plan. She would simply fight fire with fire and build her own hotel. Naturally, she called it the "Astoria"—really rubbing it in her nephew Waldorf’s face that she was the one with the family name. It was truly the ultimate power move…but a sharp, stinging curveball was coming her way.
32. She Suddenly Became A Widow
In 1892, Caroline received life-changing news. Her husband William Astor had died suddenly of an aneurysm. Adding insult to the injury of their entire marriage, he was an ocean away when it happened, and passed in the posh Hotel Liverpool in Paris, France. They had never been particularly close, but she was now truly alone and a vulnerable widow. But, as always, Caroline had a plan.
33. She Built An Enormous House
Sure, Caroline had destroyed her own home just to spitefully build the Astoria hotel—but instead of becoming homeless, she just gave herself a major upgrade on the domestic front. In due time, she’d built a double mansion further up the Upper East Side at 841 Fifth Avenue. Trust Caroline Astor to find even new ways to live the phrase "moving on up". Only, her new house had a creepy side.
34. She Was A Little Too Close To Her Son
As the only boy and the baby of the big Astor family, Jack Astor was the apple of Caroline’s eye, and she depended on him more as she got older. Then she proved her devotion in an utterly bizarre way. The big double mansion she built was actually for both of them, with Jack and his wife Ava Willing living at 840 Fifth Avenue, the next address over from Caroline. I bet you Jack’s family loved that. And Caroline’s strong will kept making impressions...
35. She Was A Narcissist
Caroline Astor had one unforgettably—and unforgettably narcissistic—trademark when it came to the lavish balls in her home. In 1890, she commissioned an enormous portrait of herself in black satin from famous French painter Carolus-Duran, and she in no way let it gather dust in the back of a closet. Oh no, she had much bigger plans for the artwork.
36. She Knew How To Stage An Entrance
Ever a woman who knew how to perpetuate her own branding, Mrs. Astor became notorious for positioning herself exactly in front of her expensive portrait when she greeted incoming guests in the front hall of her massive home. You know, in case anyone she invited forgot she was the lady of the house, let alone forgot how much money she had.
37. She Had A Mystic Nickname
The kind of fervor that Caroline Astor inspired in her friends and acolytes alike was practically unparalleled in New York at the time, and it earned her one excellent nickname. Her BFF Ward McAllister used to call the formidable socialite the "Mystic Rose" for her uncanny ability to draw people together and rule over moments of magical luxury.
38. She Made Her Rival Run Away
By now, there was no one in New York who didn’t know about Caroline’s feud with her nephew William Waldorf Astor—and, delightfully for her, everybody knew that she had emerged the winner. Waldorf was not a gracious loser, not by a long shot. After trying and failing to oust his aunt with his hotel, Waldorf quite literally ran away to England. But even there, Caroline’s power pursued him.
39. Her Nephew Nearly Disappeared
When Caroline’s nephew went to Dear Old Blighty, he was committed to never thinking of his defeat again. It reached terrifying proportions. After picking up British citizenship, William quite literally faked his own death. Why? Mostly so American papers would stop reporting what a trounce he’d gotten from his elderly aunt. This fell apart in the most delicious way.
40. No One Wanted To Mess With Her
Unfortunately for poor William Waldorf Astor, his hastily cobbled together and simple plan—which involved servants just telling reporters he’d passed from pneumonia—was immediately found out. And once word about that got around, journalists were even more ruthless about mocking him in the papers. It just goes to show: Never cross Caroline Schermerhorn Astor.
For all that, though, Caroline’s feud with her nephew had a surprising end.
41. She Created An Iconic Hotel
In a strange twist of fate, Caroline Astor and William Waldorf Astor’s legacies were united in the end. Shortly after Caroline and Jack built their "Astoria" hotel right beside the "Waldorf," the two properties merged, becoming the world-famous Waldorf-Astoria hotel, although those buildings are no longer in existence, either. Instead, the Empire State Building now stands in their place.
As Caroline moved around Manhattan, she kept making her mark.
42. She Made Central Park Cool
In due time, Caroline tired of her mega-mansion on Fifth Avenue and ended up moving into a house that directly faced Central Park. But even in these later years, the socialite remained ever herself. She continued to live with her son Jack and his wife Ava, different surroundings be darned. Only, the family was keeping another skeleton in their closet.
43. She Lost Her Mind
As Caroline Astor hit her 70s, even her indomitable spirit couldn’t withstand the ravages of time. She began to suffer from intermittent dementia, all while still putting on her best face to society and keeping a close watch of her son. (Although, as we’ll soon see, no one could predict or control what was about to pass.) And when the end came, Caroline made sure it was legendary.
44. She Went Out with A Bang
In 1908, at the age of 78, Caroline Schermerhorn Astor passed on, and she took a whole age of New York City with her. Her passing did not go unremarked: Her youngest daughter Carrie, ever eager to please the society matron even in death, erected an enormous 39-foot-tall cenotaph for her mother in a cemetery located at Broadway and Wall Street. And Caroline had one more flourish to give.
45. She Was Irreplaceable
The void that the Mrs. Astor left in the Gilded Age was felt in years to come. In fact, she was so central to New York Society that while she was the single, unchallenged head of the socialites while living, after her demise it took three prominent women—Marion Fish, Theresa Oelrichs, and Alva Belmont—to take over her position running events. Sadly, her son betrayed her memory immediately after her end.
46. She Was An Excellent Matchmaker
Like the proper little heiresses they were, all of Caroline’s daughters made gob-smackingly "good" marriages, with one girl even marrying into the Roosevelt family. At first, Caroline’s precious baby Jack followed in his sisters’ footsteps. For one thing, his wife Ava Willing was an eminently respectable socialite, and the pair had an eminently respectable two children. But the very year after Caroline passed on, Jack revealed the disturbing truth.
47. Her Son Sullied Her Legacy
In 1909, with his mother barely cold in her grave, the 47-year-old Jack sent shockwaves through polite society. He announced he was divorcing Ava, which was bad enough—but he also announced his intention to immediately re-marry…and his chosen bride was the 18-year-old society belle Madeleine Talmadge Force. In an instant, Caroline’s legacy crumbled.
48. The Astor Name Fell Apart
After decades sitting atop the New York food chain, this scandal turned Caroline Astor’s family name into mud. Almost no one in polite society could get over the nearly 30-year age difference between her son and his new bride. This led to one of the most infamous events in history. To escape the heat after their marriage, the pair went on a honeymoon to Europe to wait for things to calm down. They got much more than they bargained for.
49. Her Heir Made A Fateful Decision
In the spring of 1912, Jack and Madeleine discovered she was pregnant, and, wanting the child to be born in the United States, they immediately purchased tickets back to New York. Used to only the finest things in life, the newlyweds booked a first-class passage on the hottest new ship’s maiden voyage—the Titanic. It brought about a violent end and the last, desperate gasps of Caroline Astor’s legacy.
50. Her Baby Died Infamously
The horror that came next needs no introduction: On April 15, 1912, the Titanic sunk into the ocean after hitting an iceberg, and Caroline’s baby boy went down with the ship. Still, his mother taught him well. Though disgraced in New York, Jack’s last moments were that of a gentleman. After putting Madeleine in a lifeboat—she eventually survived—Astor was last seen calmly smoking on the deck as the ship went down. Once an Astor, always an Astor.