Alice Roosevelt was one supremely naughty girl—especially for the daughter of a President. One of the most beautiful women and most raucous socialites of her time, Alice lit up newspapers around the world with her antics, driving her father Theodore Roosevelt wild. Only, it wasn’t all harmless fun. Behind the doors of her stately homes, Alice hid dark secrets that only saw the full light of day after her end.
1. Her Birth Was A Tragedy
If you’re wondering why Alice Roosevelt turned into a wild child, look no further than the hour of her birth. Although she was the daughter of future President Theodore Roosevelt and his wife, banking heiress Alice Lee Roosevelt, the little baby was in for an immediate tragedy. Just two days after her birth—on Valentine’s Day 1884, no less—Alice’s grandmother died of typhoid fever. And this was just a prelude to the horror to come.
2. She Lost Her Mother At A Painfully Young Age
Believe me when I say that Alice was born with a lot of baggage. That’s because, mere hours after Grandma Roosevelt passed, Alice’s young mother also died in the bloom of her youth, succumbing to kidney failure that no one had even known existed. No sooner had she drawn her first breaths than Alice was a harbinger of doom. Oh, but it got ten times worse.
3. Her Father Abandoned Her
As if it wasn’t enough to have your grandmother and mother drop dead within hours of your birth, Alice’s father then dealt her a heartbreaking blow. He had loved his young, beautiful wife dearly, and now couldn’t even stand to be in his daughter’s presence after the tragedy. He immediately escaped to his remote North Dakota ranch, while sending Alice to live with her Aunt Anna for years on end. And that wasn’t all.
4. There Was One Taboo Subject In Her Life
Theodore Roosevelt was so torn up, he wouldn’t even call his little girl by her name, since “Alice” was also the name of her late mother. Instead, he called her “Baby Lee” and almost never mentioned Alice’s mother again, period. Alice herself followed suit: She avoided using her own name as well, calling herself “Mrs. L” in adulthood.
A dead mother, an absent father, and a whole bunch of repressed feelings. I mean, what could possibly go wrong? Answer: EVERYTHING.
5. Her Life Turned Upside Down
Alice’s life was already something of a tragic fairy tale. Then it turned into a catastrophe. When she was just two years old, Alice’s father remarried, this time to his old high school sweetheart, the stately and proper Edith Kermit Carow. The one problem? Cold, distant, and intellectual, Edith was about as far from Alice’s warm, romantic mother as you could get, and the transition was nothing short of disastrous.
6. She Had An Evil Stepmother
As Alice grew up, she blossomed into a young, delicate beauty who looked astonishingly like her mother. Well, her new stepmother Edith did not like this, and she made sure Alice knew it. Edith had actually known her mother before marrying Theodore, and found the elder Alice both strikingly gorgeous and unforgivably simple. Accordingly, Edith once sneered that if the woman hadn’t passed prematurely, she would have “bored Theodore to death.”
With this cruel volley, what else could Alice do but strike back? With a vengeance, that is.
7. She Was A Spoiled Brat
While this was going on, Alice’s father did still occasionally spoil her and seek out her affection, and Alice didn’t hesitate to take advantage of it. One day, she gave a brutal ultimatum. When Theodore—then the Governor of New York—and her stepmother insisted she attend a girls’ school in New York City, Alice wrote back a scathing letter.
She wrote, "If you send me I will humiliate you. I will do something that will shame you. I tell you I will.” This likely didn’t go the way she wanted.
8. She Was The Black Sheep
As time wore on, Alice’s charms wore thin even on her indulgent father, and she came to believe that he preferred her new, younger half-siblings with Edith over her. Not that this changed her behavior. Perhaps lashing out, she became even more stubborn and wild, taking up the habit of “running the streets uncontrolled with every boy in town,” or so her stepmother thought.
Alice Roosevelt was clearly no shrinking violet—and she was about to find herself front and center on the world’s stage.
9. She Became The First Daughter Amid Tragedy
In 1901, Alice’s father Theodore was serving as Vice President of the United States when a national nightmare shook Washington’s foundations: President William McKinley was assassinated. Suddenly, Roosevelt was acting president, and the teenaged Alice, still just 17 years old, became the First Daughter. Her reaction was…well, pretty ghoulish.
Despite the grim circumstance, she reportedly heard the news with “sheer rapture.” It only ramped up from there.
Sign up to our newsletter.
History’s most fascinating stories and darkest secrets, delivered to your inbox daily. Making distraction rewarding since 2017.
10. She Was A Social Celebrity
In 1902, Alice officially came “out” as a debutante. She was an instant sensation. That evening, she decided on wearing a slightly unconventional pale blue gown as opposed to a white frock and sparked a fashion trend in the process. Admirers dubbed the icy hue “Alice blue,” and women across America started wearing it. Yet behind her picture-perfect looks at these functions, Alice was already showing disturbing tendencies.
11. She Was A Bad Girl
Women of Alice’s day and age were expected to make polite appearances at parties, but Alice was having none of that. Brash, witty, and beautiful, she lit up every room she walked into…and she did a whole lot more than that. She became notorious for smoking, drinking, gambling, and staying up way later than was proper with gentlemen callers.
To add to her wild mystique, she also owned a pet she dubbed “Emily Spinach.” Believe me, though: her most infamous moments were yet to come.
12. Her Father Was Ashamed Of Her
With all of her in-your-face partying, Alice was something of an acquired taste. While her father grew actively ashamed of her, others were enraptured. Kaiser Wilhelm II, for example, let her christen his boat and then kept her photo in it at all times. Agog at her antics, the press also nicknamed her “Princess Alice” for her outsized popularity. And Alice found a diabolical way to capitalize on her fame.
13. She Was Her Own Paparazzi
In between partying with the Vanderbilts and napping well into the day, Alice was also hard at work building her own myths. President Roosevelt used to complain that gossip about Alice’s comings and goings would make the headlines above the actual news…and that’s just how Alice wanted it. In fact, she used to phone into tip lines and tell them where she was about to go so they could snap photos, earning a nice cash bonus in the process. This was a slippery, slippery slope.
14. She Played Mean Pranks
While Alice was fun to be around in her best moods, she had a terrifying mean streak. At one point, she was bored in a White House gathering and decided to put a tack on a “middle-aged” and “dignified” man’s chair, then watch as he sat down and promptly bolted by up “like the ball from the cannon” while she acted innocent beside him. Very funny, Alice.
But when it came to family members instead of strangers, she could go from mean to downright insufferable.
15. She Was Her Father’s Right-Hand Woman
As Alice grew into a fully-fledged woman, she cultivated a whopping set of brains to match her beauty, and her father Theodore started relying on her to offer presidential advice from time to time. He may have regretted it. Alice, never shy about sharing her opinions, loved flying in and out of his Oval Office for anything ranging from the lightest triviality to the heaviest political musing. One day, this led to an infamous altercation.
16. She Was Extremely Annoying
On this particular day, Alice must have been feeling particularly opinionated, because she interrupted her father no fewer than three times while he was trying to have a conversation with his friend, the writer Owen Wister. Finally, the president broke. Pushed to his wit’s end, he threatened to throw Alice “out the window” unless she left him alone, then famously huffed to Wister: "I can either run the country or I can attend to Alice, but I cannot possibly do both.”
How prophetic those words turned out to be.
17. She Scandalized Her Shipmates
In 1905, Alice joined a handful of congressmen on a diplomatic cruise bound for Japan and China, among other destinations. But one evening, it went from stately to scandalous. Bored (as usual) with the serious crowd, Alice bounded into the ship’s pool with all her clothes on, and even took a reluctant congressman with her. The consequences were immediate.
18. She Showed No Remorse
Like so much Alice did, this antic caused an immediate uproar, and years later Bobby Kennedy ribbed her about her impropriety. Alice’s response? She clapped back at Kennedy that it would have been even more scandalous if she’d done the prank with her clothes off. Still, even with all this late-night pool jumping, that wasn’t even the most outrageous thing to happen on that ship.
19. She Fell In Love On A Cruise
While sailing around the world relatively unsupervised, the vivacious Alice happened to get extra friendly with one congressman in particular: Nicholas Longworth III, a self-serious Republican with something of a hang-dog face and a reputation as a playboy. Although she’d met him before, Alice only really noticed him on the ship.
Then again, she did have a compelling reason to fall for him…
20. She Had A Sugar Daddy
Longworth was a whopping 14 years older than Alice, and more than that, he creepily bore quite the resemblance to her father Theodore Roosevelt. For reasons Freud would probably find fascinating, Alice found Longworth irresistible and admitted lukewarmly that she was “more or less” in love with him. If that sounds shaky, well, Alice started making some very shaky decisions from then on.
21. She Made A Big Announcement
By the time the diplomatic ship docked back in the United States, Alice had some news that set the gossip rags atwitter. She was engaged to Nicholas Longworth, perhaps as unlikely a groom in her sea of suitors as she could get, minus his political bona fides. Still, Alice threw herself into wedding planning with a gusto only she could muster—and she did not disappoint.
22. She Was An Attention Hog
Alice Roosevelt’s wedding was going to be the social event of the season no matter what happened, but the socialite really made sure all eyes were on her. Not only did she wear a light blue wedding dress—a nod to the “Alice blue” that she herself had coined—she also cut her massive, gorgeous wedding cake with a sword she borrowed from a military aide during her reception. Mmm, might be a bit much, Alice.
After a honeymoon that included visits to the likes of King Edward VII and Kaiser Wilhelm of Germany, Alice and Longworth settled into a quiet, happy life of domestic bliss. JUST KIDDING, it was an absolute nightmare.
23. Her Marriage Tread Dangerous Ground
For the first years of her marriage, Alice and Longworth got along famously, but the ties that bound them were already fraying at the edges. The two loved to party until all hours of the morning, but while all that was fun and games during their courtship, the strain began to show once they were husband and wife. In other words, there was nowhere to go but down.
24. She Turned On Her Husband
In 1912, Alice dealt Longworth one of the worst betrayals she could: She publicly opposed his run for election. Instead, she supported her father’s preferred candidate, appearing on stage alongside the rival and using her fame to drum up interest in him. The damage was enormous and irreparable. Longworth lost—and when he did, Alice proudly boasted that she was the reason.
For some couples, maybe this love-hate thing would get their rocks off. For Alice and Longworth, it created an enormous rift. One that grew wider with Alice’s next move.
25. She Was Promiscuous
Just when Alice’s eyes started straying is hard to pin down, but it’s an absolute fact that she carried on multiple affairs behind Longworth’s back—or heck, even in front of him. Her paramours were an open secret amongst the White House elite, and given her powerful father, Longworth pretty much had to grin and bear it. Of course, Longworth carried on his own dalliances, too…but then came the most devastating blow of all.
26. She Had An Illicit Love
One of Alice’s most prominent and long-term affairs was with Senator William Borah, a man who, like Longworth, was decades older than her but apparently much steamier in the bedroom. Although Borah had also long been a married man, he and Alice were frequently sneaking about town with each other. Until, that is, they got a very harsh wake-up call.
27. She Had A Lovechild
Around 1925, Alice found out shocking news: After more than a decade in her childless marriage to Longworth, she was pregnant. Those in the know in Washington suspected that Borah—whose own marriage was equally childless—was the father, and Alice’s own diaries all but confirm she was about to have his lovechild. But when the child was born, well, Alice took it right up a notch.
28. She Was Malicious
Fun-loving and smart, people often described Alice Roosevelt’s humor as “brilliantly malicious,” and she saved her cruelest dig for her cuckolded husband. Although she ended up naming her baby girl Paulina, she once quipped that she initially wanted to name her “Deborah,” as in “de Borah.” Ouch. As it was, anyone who knew the girl nicknamed her “Aurora Borah Alice.” Double ouch. Still, Alice was just getting started.
29. She Was A Bad Mother
Truth be told, Alice was about as good a mother to Paulina as she had been a faithful wife to Longworth. Wrapped up in her glittering world of social events—at her height, she went to over 1,000 events in just 15 months—Alice didn’t have much time to raise Paulina, and they never developed a close bond even in adulthood. As we’ll soon see, this would come back to haunt her.
30. She Got A Tragic Telegram
In 1919, Alice was only really just getting on her feet as a bona fide adult when loss hit her like a speeding truck. That January, her father Theodore suffered from a fatal blood clot that had traveled to his lungs, dying suddenly at the age of just 60. The horrible news came with just one devastating line. Her half-brother Archibald telegraphed the siblings, “The old lion is dead.”
Unfortunately for Alice, the hits just kept on coming.
31. She Lost It All
In the 1930s, Alice suffered a blow unlike any she’d ever felt before. With the infamous stock market crash, her high-flying life also took a complete nosedive, and she and her husband lost a great amount of their wealth. So much so that the once untouchably elegant Alice started making tobacco commercials to supplement her income. But if she thought she’d hit rock bottom, she was very wrong.
32. She Entered A New Phase Of Her Life
In the 1940s, Alice became a grandmother after her daughter Paulina marred the American artist and author Alexander McCormick Sturm and had a child, Joanna, with him. It looked like the great American golden family were back in their glory, yet as with so much in Alice’s life, appearances could be deceiving. In reality, she was about to go through a dark crisis.
33. Her Family Fell Apart
Ever since her cold and distant childhood, Paulina had difficulty maintaining any kind of happiness, and her marriage had no happy ending, either. In 1951, when baby Joanna was still a young girl, Alexander Sturm passed suddenly of hepatitis, leaving Pauline grieving and Alice struggling to pick up the pieces of her family. But she had never been good at caregiving…
34. Her Daughter Made A Heartbreaking Confession To Her
Soon enough, Alice’s private life had reached a disturbing climax. Paulina was so depressed and bereft that she almost couldn’t go on, and she confessed as much to her icy mother. It must have taken everything in Paulina, but she begged Alice that if anything should happen to her, that Alice would take over the care of little Joanna in her stead.
When Alice agreed, she may not have known she was helping seal her daughter’s tragic fate.
35. She Lost Her Only Daughter
In 1957, Alice received the most dreaded news: Paulina had passed from an overdose of sleeping pills, just six years after losing her husband. But while Alice may have been a good time gal when it suited her, she was also a woman of her word, and she immediately fought to gain custody over Joanna, just as she’d promised Paulina during her last days. Then everything changed.
36. She Tried To Atone For Her Sins
Whether out of guilt for her previous maternal go-round or a newfound maturity, Alice treated Joanna almost the opposite of how she treated her daughter. She doted on and spoiled the young girl, and the pair became inseparable. As one friend put it, Alice “has been a wonderful father and mother to Joanna: mostly father.” Of course, this doesn’t mean Alice was losing her edge…in fact, as some powerful men soon found out, she was sharpening it.
37. She Was Powerful
As “Princess Alice” grew older, she practically became Dowager Empress of America, and she wielded a terrific amount of political power. When a man named Thomas Dewey tried to become president, it was Alice who made sure he would be forgotten in the annals of history. When she unfavorably compared his looks to “the bridegroom on the wedding cake,” it was enough to almost singlehandedly lose him two presidential elections in a row.
As always, though, Alice saved her worst vitriol for those closest to her.
38. She Insulted Her Cousins
Alice had a sharp tongue, and it got her into a nasty family feud. When her distant cousin Franklin Delano Roosevelt—who was married to her even closer-knit cousin Eleanor Roosevelt—started aiming for the presidency, Alice made no bones about how much she disliked him and his bid for the top spot. She even gave a public interview where she sneered that, “the same surname is about all we have in common.”
Nonetheless, there was one Washington family she got very close to.
39. She Had An Unlikely Friendship
As the star-spangled Kennedy family rose to the top of the American power game in the 1960s, Alice was right there along with them. Although she didn’t vote for John Kennedy, she took a shine to the clan’s innate glamour and developed a particularly tight friendship with Bobby Kennedy as she entered her twilight years. Except, well, this is Alice. So she managed to muck that up…
40. She Was A Mean Girl
Although Alice and Bobby Kennedy were unlikely but intimate friends, they often had rifts with each other—and Alice was usually at fault. One of her ice-cold barbs went deep. At one point, Bobby Kennedy had performed the none-too-shabby feat of climbing the newly-minted Mount Kennedy in Canada…and Alice didn’t hesitate to ridicule him for it, creating yet another big strain. And this wasn’t even her worst friend breakup.
41. She Was A Kingmaker
One of Alice’s most famous friends was then-Vice President Richard Nixon. Not only did Nixon act as one of her pallbearers when her daughter Paulina suffered her tragic end, but Alice also encouraged his political career, consistently and insistently inviting him to all the right parties until he did become President. Instead of gratitude, however, Alice only got betrayal.
42. The President Stole Her Words
In the 1970s, the Watergate scandal hit, and Nixon’s name was permanently tarnished. But that was just the beginning of the nightmare for Alice. At his resignation, the disgraced Nixon decided to quote from one of Alice’s published diary entries, specifically the one recalling her father’s grief over her late mother, where she wrote that "Only if you've been to the lowest valley can you know how great it is to be on the highest mountain top."
In case you’re wondering how Alice felt about that, the answer is: She went wild with rage.
43. She Was A Rage Watcher
Never one to miss a beat, Alice made sure to watch Nixon’s resignation on her television, and when she heard her now ex-friend using her own words to justify his shady actions, she did not take it lightly. Um, not at all. Reacting in with the classic Alice gusto, she reportedly let out a string of curses at her screen and denounced him as her friend. She did, however, leave her best snub for last.
44. She Snubbed Jimmy Carter
After a lifetime of infamy for her sharp wit, Alice had made a whole series of Presidents quake in their boots, kick her out of their sight, or both. But when it came to President Jimmy Carter, he never had the chance to do either—because Alice refused to meet him. Her reasons were classically cruel. She thought he was uncouth, so didn’t want to give him the honor.
45. She Was Just Like Her Father
Alice had a complicated relationship with her father—although, which one of her relationships wasn’t complicated?—but she also identified with him on a deep level. Like her, Theodore Roosevelt craved attention and was smart enough to get it whenever that craving hit. As she once said of him, "He wants to be the bride at every wedding, the corpse at every funeral, and the baby at every christening.”
46. She Loved Gossip
Alice Roosevelt’s bon mots had lit up the American public gossip mills since she was a teenager, but few people realize she took her instinct for drama right into her own private home as well. Roosevelt famously had a pillow on her living room settee that proclaimed, “If you can’t say something good about someone, sit right here by me.” Don’t mind if I do, Alice.
47. The White House Kicked Her Out
Eventually, all good things come to an end—and although Alice’s miserable marriage kept going against all odds, her father Theodore’s tenure as President didn’t. In 1909, he left the White House to make way for the 27th president, William Taft. But after all her years as First Daughter, Alice was none too happy to give up her privileges…and she let the new occupants know it in a terrifying way.
48. She Played A Cruel Practical Joke On The First Lady
As she was leaving the White House with her father, Alice left a disturbing goodbye “present.” She had made a voodoo doll in the likeness of the incoming First Lady, Nellie Taft, and upon her exit, Alice buried the grim doll in the front yard of the property. Evidently, Alice never quite clicked with the Tafts, and they even later banned her from the White House. And that wasn’t the last time she got into Washington hot water…
49. She Mortally Offended A President
If Alice didn’t get along with the Tafts, she really didn’t play nice with the next president, Woodrow Wilson. In fact, they were downright enemies. In 1916, Alice decided to crack a bawdy joke making fun of the current President, who then immediately kicked her out of his sight and his property, making it her second dis-invitation to the White House.
50. She Went Out With A Bang
In the end, Alice outlived all her younger siblings, as well as so many other giants of American history who she had met and even shaped. Still, even she couldn’t live forever. On February 20, 1980, she passed in her Embassy Row house in Washington D.C. The cherry on top? She made it just eight days past her 96th birthday. An overachiever until the end.