Gossip Girl Was Actually a Documentary
The real-life aristocrats who made the Gossip Girl crew look like saints
There are a lot of ways Gossip Girl, which first aired in 2007, dates itself. Now that Gen Z is older than Serena, Dan, Blair and Chuck were, it’s hard to imagine a world in which Millennials were cool and cutting edge. Watching fashionista Jenny Humphrey confidently wear a fedora and a vest over a white t-shirt (a look that had a death grip on the late aughts) is cringe-worthy now. The top-of-the-line Blackberrys or flip phones that Upper East Siders would use to check Gossip Girl or toss in a trash can look ancient next to even early generation iPhones. Nelly Yuki getting dumped at a Flo Rida concert... Serena winning a Guitar Hero championship at Blair’s classy penthouse birthday party... Chuck’s basketball getup… A moment in time if I ever saw one.
Trends change faster than the seasons, and yet.
There’s something about the drama, the pace, the drumbeat of Gossip Girl that make it timeless. And maybe that’s because even the more outlandish stories of wealth, love, betrayal and greed, have been recycled throughout history, especially in the Big Apple. As one TikToker pointed out, “You can look in the history of New York City, any era, and you will find in the socialite scene a Blair, a Serena and a Chuck.”
So I decided to become a historian and hit the books (by books do I mean Wikipedia? That’s not a secret I’ll ever tell) to share with you all, as a little Thanksgiving-eve treat, some real life events Gossip Girl may have drawn inspiration from: the story of the Waldorf-Astoria hotel.
Fair warning that if you paid attention in 10th grade U.S. history class and you don’t have a brain that completely discards information the minute you learn it like mine does, you might already know all of this. Or if you’ve watched Max’s The Gilded Age, I’m assuming this is kind of roughly what it’s about? I am tempted to watch and see for myself but 1) I am not convinced Meryl Streep’s daughter can act 2) I’d rather put respect on Christine Baranski’s name first by finally watching The Good Wife and 3) Although Cynthia Nixon does have a face that looks like she’s never seen an iPhone, it’s hard for me to separate her from Miranda let alone her gubernatorial race with Andrew Cuomo (most of you have forgotten but I have not).
Anyway, brace yourselves, Upper East Siders, because this is a juicy one.
William Waldorf Astor, born in 1848, was a staple in New York’s gilded age. He was a lawyer, a politician and a connoisseur of the arts. But while Astor was already rich, the death of his father in 1890 made him rich, rich. The second richest man in America only next to John D. Rockefeller. Rich enough to be petty.
See, William had an aunt named Caroline Webster "Lina" Schermerhorn Astor, who outranked even the wealthy Astor family she married into as a descendent of the original 1600s Dutch settlers of Manhattan otherwise known as the... wait for it ... Knickerbockers.
I’m just going to put this plainly: Caroline, Lina, whatever you want to call her, was a cunt. She was literally known as the gatekeeper of Manhattan society. She spent most of her days being judgy in a brownstone on Fifth Avenue, but she and her husband also owned an estate in Newport, Rhode Island with a grand ballroom used to host “The 400” -- the 400 people in New York who Caroline deemed to be members of “Fashionable Society.” She held such a tight grip on the aristocracy in New York City, it took her years to finally anoint the mega-wealthy Vanderbilt women as members of the 400, deeming railroad money to be “dirty.” She was everything Blair wanted to be. I’m quite confident our Queen B would have sold out at least two of her closest friends just to be let into one of Lina’s elite parties, and we would have rooted for her while she did it.
But by inheriting both his father’s fortune and his esteem in 1890, William Waldorf effectively became the head of the Astor family and so he decided that it was time to take Aunty Caroline down a notch (What did I say? Mega rich = petty).
Lina’s husband was also named William and so her name on the streets of the Upper East Side formally was “Mrs. William Astor.” But this simply wouldn’t do. William Waldorf Astor didn’t want anyone getting Miss Uppity confused with HIS Mrs. William Astor, Waldorf’s wife Mary or “Mamie”. But Mary was a nobody and Queen L was not about to have her own name stolen by some bland broad18 years her junior named Mamie. And I don’t blame her! The audacity of this man!
So Lina said no <3. And although William had buckets of money, he didn’t have near the social capital Lina had built up with years of blood, sweat and tears (all metaphorical, I’m sure her white cotillion gloves never had even a speck of dirt on them). Needless to say, all of his efforts to sabotage Lina were thwarted.
Now at this point I must disrupt the flow of the story to tell you that based on my very extensive googling and Wikipedia-ing, two competing timelines of what happens next have emerged. Full transparency, I am just choosing the more dramatic one. Is it entirely correct? Probably not but take that up with Wikipedia. They say the victors write the history books but personally I think it’s the drama queens. Have any of you actually read the Bible?? Anyway..
In very Blair fashion, Lina essentially banished William from Manhattan. He fled with his family to England where he could become a viscount as a little treat.
But there’s nothing more dangerous than a rich man with a bruised ego. The Atlantic Ocean did not stop Lina from living rent free in William’s mind, and he decided he’d have the last laugh.
William started making plans to have his father’s house, which happened to be next door to Lina’s mansion on Fifth Avenue, torn down and replaced with a 13-story hotel. Not only was the construction noisy and annoying, the structure would quite literally overshadow Lina’s luxury estate and all the other buildings on the block. He’d call it the Waldorf Hotel.
Was this an effective and creative plot to further a family feud? Absolutely. Was it a complete and total win for Willy? Absolutely not. Our man could not catch a break. As the hotel was being constructed, he got railed by the press, making fun of him for putting too many bathrooms in the floor plan and calling the hotel “Astor’s Folly.”
Between Lina pantsing him in polite society and the mockery of his hotel, William was so down and out, he appears to have faked his own death just to get the haters off his back. Most historians can at least make an educated conjecture that Astor had his staff report to American reporters that he perished from pneumonia. But William, who if you haven’t noticed by now is clearly the Serena van der Woodsen in this scenario, did not even come close to pulling this off. Within days, the media caught wind that William was faking it and resumed mocking him mercilessly.
Still, if this man’s one goal in life was to be petty (which seems likely) he was succeeding. Lina had to have been royally pissed off by this weaponization of real estate. Unwilling to be neighbors with the riff raff at The Waldorf, which she called a “glorified tavern” (this woman hated immigrants more than Trump did, so you can imagine how she felt about tourists), Lina nearly resigned to tearing down her mansion and turning it into stables. But enter, JJ, Lina’s son.
If William Waldorf is a shadow of Serena van der Woodsen, it’s easy to see how Chuck Bass’ fierce loyalty (except when it’s inconvenient for him, honestly) to his own Queen B might have been inspired by Lina’s loyal, and equally petty, son John Jacob Astor IV.
JJ said to Lina, “Hold on a minute, I am also a wealthy Astor man and I can sling my dick around Manhattan just as well if not better than this loser half-Brit with a receding hairline.” JJ resolved to tear down his mother’s house and build another hotel, a bigger hotel. And as a true family man, he named it The Astoria.
That this hotel next door was an entire four stories higher than William’s AND bore his family name was a major blow. Waldorf might have won one battle but Miss Lina was always going to win the war.
However, just as Serena, Blair and Chuck (and Nate, but he’s not usually doing that much. The series was pretty spot-on when it made Nate a descendent of the Vanderbilts who were really just not apart of all this) frequently did Lina, JJ and Willy realized they were stronger united than squabbling with each other. They remembered that in the end they were family, which, if anything, meant they can all share in one giant pot of gold. They formed a truce, merging the two hotels together by constructing a small passageway called “Peacock Alley,” which is really so fitting I’m wondering if Lina came up with it.
To think, a hotel empire built solely upon a man just failing to leave a successful woman alone.
But the two cousins JJ and William would continue competing with each other for years to come. The family makes Gossip Girl’s cycle of constant competition fueled by greed and the pressures of upper class society appear to not just be fodder for some good entertainment, but also a pretty realistic representation of, as Kristen Bell’s voiceover would phrase it, Manhattan’s elite.
So the next time someone tries to tell you that Gossip Girl writers were outrageous for writing that Bart Bass faked his death, just remind them life is usually stranger than even the silliest of fiction. Yeah, Bart eventually getting pushed off the Empire State Building was maybe a little bit of a stretch but, let’s not forget, JJ Astor would later go on to die tragically upon a major historical structure also….
Don’t forget reply to this email with a Gossip Girl moment you just can’t stop thinking about. It can be as big as Chuck buying a burlesque club at age 16 or as small as Serena wearing her graduation tassel in her hair instead of a cap. We’ll compile these all for a Friday post. And catch up on this week’s posts about which characters deserved better and worse and coming to terms with Chuck and Blair.