We Miss Catty Sassy Trump

Before he was the President, he was the Queen of Sass. We miss him.

Many people knew who Donald Trump was before he ran for President in 2015, but most of what they knew about him probably had to do with his celebrity status and the Trump brand. They knew about Trump Tower, they knew about The Apprentice and they knew about his catchphrase, “You’re fired.” But the thing that I knew about him, more than anything—the thing I was obsessed with—was his feud with Rosie O’Donnell.

If you watched the Republican primary debates for the 2016 election, you probably noticed his rebuttal to Megyn Kelly when she asked him about his disparaging rhetoric toward women. “You've called women you don't like fat pigs, dogs, slobs, and disgusting animals,” she said. His retort? “Only Rosie O’Donnell.”

My take on Trump’s infamous rebuttal

He was referencing their notorious 2006 feud, which began when Trump decided to give a second chance to a Miss USA contestant who had some sex and drug-related scandals. Rosie O’Donnell slammed Trump on The View by cartoonishly combing her hair over and doing a pretty terrible Trump impression, satirizing the fact that a twice-divorced reality show star should be the moral authority on anything. She then said he was “bankrupt” which was probably what triggered Trump to respond. His initial response was, “I’ll most likely sue her for making those false statements – and it’ll be fun. Rosie’s a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie.”"

But this wasn’t the end. Trump repeatedly referred to Rosie O’Donnell as a “loser” but his insults continued over the next several years, culminating in this tweet when Rosie got engaged:

I’m sorry—look, I hate Trump as much as the next liberal but this tweet is just flawless. He then cheekily tweeted this a year later, when Rosie survived a heart attack:

But nothing beats his ultimate Rosie tweet, a full eight years after the feud began:

Trump’s feud with Rosie O’Donnell was the beginning of my Trump obsession. I didn’t like him then either—I mean, he was clearly an asshole. But damn, was the man funny. And he wasn’t funny in a crude, guys’ guy way, which was the fashion at the time (think Family Guy, Dane Cook, Stiffler from American Pie, etc.) Trump was funny in the way that—okay, to quote Trump himself this isn’t very politically correct, but he was funny in the way that previously, only gay guys could be funny.

This isn’t to say that Trump is gay. I’m confident he’s not, and I think people who attempt to make fun of him for being gay are exposing their own thinly-veiled homophobia. I do, however, think Trump is “queen-coded.” And to be clear, this is not an insult. It’s the only good thing about him, aside from Operation Warp Speed and his underrated plan to buy Greenland.

Trump being the straightest queen to ever exist is backed up by many things. Take, for example, his love of Broadway. Trump’s favorite Broadway shows are Evita and Cats, and he loves Broadway so much that purportedly, he had a staffer nicknamed The Music Man who would play Broadway showtunes to calm him down.

He also seems oddly at ease with his own masculinity or lack thereof, something that I don’t think people notice because he has aligned himself with a party that values machismo above all else. I know what you’re saying—that’s not true, Trump is the ultimate in machismo. Where did you hear that, MSNBC? It’s not true. Trump does, however, abide by the compass of Weak vs. Strong. It just so happens that Trump doesn’t care who the Strong person is—all that matters is that he humiliate and dominate the Weak person. One could call this toxic masculinity, but it’s the mindset of many a seventh grade mean girl, or—dare I say—reality show winners.

What made Trump so effective in the crowded 2016 Republican primaries was that he treated each debate like a rose ceremony, allying himself with the stronger contenders to bully the weak—who could forget how he went full 9/11 truther to go after the ultimate beta cuck of the group, Jeb Bush? As the kids like to say, Trump lowkey mogged him with rizz. It didn’t actually matter what Jeb Bush had said or done. Trump sniffed him out as the weak one, and acted accordingly. It’s exactly how he functioned when he was actually doing reality TV.

Take for example, one of Trump’s best moments from The Apprentice. The contestants had to create some kind of business seminar, and one contestant, Clay, had chosen to teach a seminar about “sex in the workplace,” which included the acknowledgment that he was gay. A different contestant, named Adam, said that Clay’s homosexuality, and the mention of it in the seminar, made him uncomfortable. Keep in mind this was in 2005, when casual homophobia was largely tolerated by society.

I expected Trump to bully Clay for being gay. But instead, he asked him, “Are you a homosexual?” When Clay said yes, Trump shrugged, attempting not to care, and said, “Okay.” He then interrogated other members at the board room to discover that other people were informed Clay was gay, and he was not. He didn’t care that Clay was gay. He cared that nobody told him. He then asked, “Did everybody know this?”

He wanted the tea!!!

Trump went on to say that “this is why we have menus in restaurants. Some people like steak, some people like spaghetti.” He then pivoted to bullying Adam for finding Clay’s homosexuality so provocative. That’s because Trump doesn’t care who’s masculine or who’s straight. He cares who’s strong. And Adam, frankly, was weak.

He asks Adam if he’s ever had sex before (Adam, weirdly, refuses to answer.) He then sums it up with this withering monologue: “Listen, Adam isn’t good with sex. You might be in ten years but right now you don’t feel comfortable with sex. You will. Someday, you will. It’s gotten me into a lot of trouble. It’s cost me a lot of money. You understand that? You’ll probably be there. In many respects I hope you are. Because there’s nothing like it.”

This interaction perfectly sums up Trump’s attitude toward masculinity and why the Lamestream Media gets it wrong. Trump is aggressive. He’s obsessed with being dominant. But he’s not dominant in a traditionally masculine way. He’s…kind of a messy bitch.

Take, for example, in the 2016 primaries, when Rand Paul accused him of dispensing childish jabs about people’s appearances and Trump shot back, “I've never attacked him on his looks, and believe me, there's plenty of subject matter there.” He tried to be Sassy Trump on the campaign trail and as President, and in many ways he succeeded (frankly.) But it just wasn’t the same, even when it was absolutely hilarious:

I realize that for many people, especially younger people, they mostly know Trump for the more sinister headlines: Project 2025, his selection of terminally online groyper ally JD Vance as VP, his mishandling of the covid pandemic. And those are, arguably, the more important things to know. But it occurred to me that a lot of people are living only with the knowledge of Sinister Dictator Trump, with no experience of Sassy Queen Trump. That must be why a video of Trump dispensing relationship advice to a young woman on the Wendy Williams show went viral in June of this year. He seems truly happy in his environment as one of the gals. His advice is respectful and honestly pretty smart. It pains me to watch stuff like this, as funny as it is, because this is what he was meant to be doing!

Trump was not meant to be President. Trump was meant to have his own daytime talk show, one part gossip, one part snarky red carpet fashion critiques, one part genuine relationship advice for women. Trump would be the only man in the room. He wouldn’t flirt with any of the women except to say things like, “Believe me, looking at you, you will have no trouble getting guys.” He’d be their bestie.

Allow Twitter’s completely unleashed AI to paint this picture for you:

This was his destiny. We are in the Bad Timeline in which this daytime talk legend and Broadway guest star somehow winds up being the President. The last time Trump was truly happy was probably his SNL appearance during his first campaign, and even that is debatable. This was Trump in his element:

Of course, I do not want Trump to win another term. Many people who follow this Substack probably agree. But I think on some level, even Trump agrees.

This isn’t you, Sassy Donald. Turn back now. Start your talk show. We miss you.

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