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President Donald Trump, an infamous businessman, gets a kick out of a good rebrand — a strategic pivot, if you will. Whether juvenile or cutting, his insults serve as labels that stick… sometimes. Some of these name-calling campaigns have been incredibly effective, and others? Just… no. See, Trump’s kind of like your friend — who just took up stand-up comedy — running their lines by you in casual conversation… And depending on your reaction, it becomes part of their routine.

So let’s see which ones stuck and which sucked.

The Hall of Fame

These ones landed — whether we like it or not.

Joe “Sleepy Joe” Biden

Take a shot every time you’ve heard this one. “Sleepy Joe” was an incredibly catchy moniker — so much that voters on both sides have likened Former President Joe Biden’s final moments in office to the 1980s classic, "Weekend at Bernie’s,” where a couple of teenagers take advantage of their deceased employer’s beach-house for a weekend of partying while parading him around like a puppet. And perhaps this nickname deserves some credit. Yes, Trump called Biden “sleepy” before he lost to him, but the nickname lives on.

“America cannot afford four more years of a ‘Weekend at Bernie’s’ presidency,” Florida Gov. Ron DeSantis said at a 2024 Republican National Convention.

Ron “Ron DeSanctimonious” DeSantis

Speaking of DeSantis, Trump enjoyed calling him “Ron DeSanctimonious” until, of course, DeSantis dropped out of the presidential primary and endorsed Trump — that’s when he announced the nickname’s retirement. Perhaps a bit rich of Trump to call someone else sanctimonious, but it did roll off the tongue well. Even its victim himself, expressed his approval to Piers Morgan on his show: “I don’t know how to spell the 'sanctimonious’ one. I don’t really know what it means, but I kind of like it. It has a lot of vowels.

Steve “Sloppy Steve” Bannon

Thanks to its visual element, this one was particularly impactful. Steve Bannon’s disheveled appearance — while on-trend for rich dads on the California coast — is an easy target for a New York politician with Edna Mode’s instinct for critique.

Notably, he shelved the moniker with last season’s trends after Bannon — despite being called “sloppy” — publicly praising his critic on live television… Trump then responded with a tweet, calling Bannon one of his “best pupils.”

The Hall of Shame

When the insult doesn’t land, it’s just embarrassing.

Jerry “Moonbeam” Brown

This one wasn’t actually a Trump-original — dating back to the 1970s — when a columnist for the Chicago Sun-Times, Mike Royko, famously called the then-California governor, Jerry Brown, “Moonbeam.” In the end, Brown had the last laugh as Royko watched the country evolve toward Brown’s vision and, in turn, attempted to revoke the moniker — until 33 years later when Trump revitalized it with a tweet.

Royko first coined the term referring to Brown’s demographic of young voters with an allergy to tradition. “If it babbles and its eyeballs are glazed,” he wrote in 1979, “it probably comes from California.” But as any New Age Californian can confirm, such animosity is often love lost in translation — as it was for Royko who eventually spent years trying to scrub the nickname, calling it “an idiotic, damn-fool, meaningless, throw-away line” in 1991.

“Enough of this ‘Moonbeam’ stuff,” he decided. “I declare it null, void, and deceased.”

For the record, Brown’s office quickly responded to Trump’s claim, explaining that the formerly incarcerated had been “out of custody for at least 10 years and the majority were convicted of drug-related or nonviolent crimes… A pardon may be granted to individuals who have demonstrated exemplary behavior and have lived productive and law-abiding lives following their conviction.”

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Ron “Meatball Ron” DeSantis

The Italian-American Florida Governor, DeSantis, lived rent-free in Trump’s mind, earning himself a handful of pet-names. This one though? Among the weakest — forced, forgettable and lands with a thud — perhaps why Trump himself denies ever using it.

After a poll indicating that the two were neck-in-neck for the Republican nomination was published and Trump lobbied many insults against DeSantos. The New York Times reported that he was posting Ron-related innuendos on Truth Social, and continued his insults toward the governor in casual, private conversations, calling him “Meatball Ron” — an accusation that apparently disturbed the President.

He took to Truth Social: “I will never call Ron DeSanctimonious '‘Meatball’ Ron…It would be totally inappropriate to use the word ‘meatball’ as a moniker for Ron!”

Did we ever think we’d see the day the Commander in Chief in the war on WOKENESS monitor how appropriately backgrounds and appearances are mocked?

Letitia “Peekaboo” James

In a clunky and convoluted message on Truth Social, Trump referred to New York Attorney General Letitia James as “Racist A.G. Letitia ‘Peekaboo’ James.'“ Now this one’s weak because of its lack of clear meaning — Was it about hide-and-seek? A childhood insult? Or a popular interpretation — a not-so-subtle way of saying an old-timey slur for Black people, starting with "jig.” His then-spokesman Steven Cheung pushed back against this theory, writing in an email that “anyone who thinks ‘peek-a-boo’ is a racist phrase is obviously sick in the head and their assertion strains credulity and should not be taken seriously,” but didn’t clarify its meaning.

Honestly, this one is just confusing, strange and potentially offensive on a historic level.

Elaine “Coco Chow” Chao

After Former President Biden signed a bill that would keep the government funded and prevent a partial shutdown, Trump posted to Truth Social, “[Mitch McConnell] Must immediately seek help and advice from his China loving wife, Coco Chow!”

This one wasn’t great. And it reminds me of when he said it would be “totally inappropriate” to call the Italian-American Florida governor “Meatball Ron,” but it seems that principle doesn’t apply to the Taiwan-born Elaine Chao, whose parents have high-level political connections in China — especially since he doubled down.

That’s when Chao responded in a statement: “When I was young, some people deliberately misspelled or mispronounced my name. Asian Americans have worked hard to change that experience for the next generation. He doesn’t seem to understand that, which says a lot about him than it will ever say about Asian Americans.”

Kamala “Laffin’ Kamala” Harris

This one is just a verbal fumble — like a dad joke with bad intentions, the execution was dead on arrival and the intention was clear: Someone who laughs isn’t to be taken seriously — an already uphill battle for women in male-dominated industries. Ultimately, it was part of a larger narrative to paint Harris as his unserious and underprepared opponent. And he was married to it — but its greatest offense? The insult lands like a mouthful of dry toast.

The Power & Pitfalls of Trump’s Name-Calling

Love him or hate him, Trump understands marketing — evident in both his nicknames and his ability to get half the country to defend his claims that Haitians in Ohio are abducting and eating their neighbors’ pets. And while some of his nicknames were undeniably effective, others fell flat on their face — or were so outlandish that even his most followers struggled to justify them.