T.W.E.E.T.: Trump’s Worst Ever Embarrassing Tweet

An Arc Digital tournament challenge

Berny Belvedere
May 1, 2020 · 20 min read

The time has come to choose Trump’s worst ever tweet.

I know, I know, there are more Bad Trump Tweets than there are grains of sand on the shores, or stars in the sky, but life under quarantine has enabled me to pursue a research opportunity of this magnitude, and By Jove I do not intend to squander it.

In March, I organized a tournament pitting the worst quotes I could find from the Democratic primaries against each other. A winner was crowned: Julian Castro.

The winner this time will be Trump. Because there’s only Trump. This is an All-Trump tournament. I have narrowed it down to 64 entries, but let me tell you, we could’ve ran a thousand.

There are four regions, with 16 entries per region. Although Trump has been tweeting since 2009, I have divided the tournament into his pre-presidency phase (2009–2016) and his presidency phase (2017-present).

There is no single quality that makes a Bad Trump Tweet. You’ve got the usual suspects: his unearned arrogance, his unrepentant belligerence, his extremely suspect grasp of the concepts he’s tweeting about. But there are also more subtle indicators of a mind in full command of bad tweeting: grotesque misspellings, random musings, mind-boggling weirdness. Some are serious. Some are hilarious. All are awful. But each matchup asks a very simple question: Which of the two is the worse tweet?

As with last time, I supply the quotes, you supply the votes.


(1) Kenya vs (16) Dunes

(1) Kenya

So, the birther stuff, right? Although Obama’s shining moment at the 2004 Democratic convention was electrifying to political observers, most Americans got to know him during the 2008 Democratic primaries. But since he hadn’t been in national politics for very long, and since he is black with a “funny name” (as he himself has put it), bad actors exploited this information gap and racially targeted him by suggesting he’s foreign born. But, well … check the time stamp there. We’re in the fourth year of this human being’s presidency and Trump is advancing rank birtherism. Being a birther in 2008 was bad enough; my guy was birthering in 2012. Reprehensible stuff.

(16) Dunes

There are many impressive components here, most of them centering on Trump’s decision to include the word “geomorphology” in an actual tweet. First, there is the spelling, which—sit down for this—is somehow correct. Then, there’s the suggestion, from Trump himself, that he has learned something. Learning implies going from ignorance to knowledge, and Trump hates to convey that he’s ever in his life endured the indignity of ignorance. But there it is: he tells us he has learned something. Finally, there’s the weirdness of what he has learned. Donald Trump absorbing insights about movement landforms is unimaginable to me. Or maybe it’s because my geomorphology doctorate from Trump U didn’t really teach me anything.

(8) Barney vs (9) Civilization

(8) Barney

Trump calling out former Congressman Barney Frank on failing to suppress his powerful nipples is quite the Twitter moment. But it’s when Trump evaluates it as “disrespectful,” as though Frank went into Congress looking to flaunt his nips, with total disregard for proper blue shirt wearing protocol, that makes this one a true classic.

(9) Civilization

Trump’s elemental indecency is on full display in a lot of these. In this particular tweet, he says that taking in people from Syria spells the end of civilization. Imagine saying that. Imagine thinking that. There are reasonable arguments for robust immigration-restrictionism. But likening the taking in of Syrians with the end of civilization itself is grotesque.

(5) Autism vs (12) Wade

(5) Autism

“Doctor-inflicted autism.” What an inveterate crank.

(12) Wade

Dwyane Wade, the greatest Heat player of all time, might have expected that his family member’s death remain unpoliticized. But that would be quite naive on his part to think this. Welcome to having your cousin’s death repurposed as an extremely tactful advert for Trump’s capacity to be so very great for the black community.

(4) Gross vs (13) Groveling

(4) Gross

Impeachment, you say? This tweet, going all the way back to 2014, is too perfect.

(13) Groveling

We are supposed to believe that simulating a deformed arm with an open mouth—something that, to our collective shame, literally every middle schooler in America knows is a way to mock a disabled person—is Trump’s special way to make fun of “groveling.” Yup. That totally checks out. Trump is constitutionally indecent.

(6) Windmills vs (11) Mosque

(6) Windmills

This tweet was lovingly crafted by Donald J. Trump to inform the public about the greatest threat to both bald and golden eagles. After chewing on that tasty morsel of information, Trump tacks on a nuclear take to the end of this tweet, almost as an after-thought, about “fictional global warming.” Imagine inhabiting Donald Trump’s brain.

(11) Mosque

A thought experiment for the ages! Back when the thinking emoji was just a sperm cell in Charlie Kirk Sr.’s reproductive member, Trump was delivering POWERFUL hypotheticals of this caliber.

(3) Flag vs (14) Cruz

(3) Flag

I give Donald Trump a pass for not being familiar with the obscure constitutional technicality known as the First Amendment. It’s only been around a couple centuries. Cut him a break, fam.

(14) Cruz

Trump is almost impossibly superficial. What does Trump mean by “I will spill the beans on your wife!”? Typically, that refers to exposing a secret about someone. But Trump doesn’t know anything about Heidi Cruz, Ted’s wife. He only knows what she looks like. So, for Trump, “spill the beans” likely meant “inform the public about how she’s not attractive.” This is borne out by Trump’s retweeting a follower’s tweet showing a nasty juxtaposition between Melania and Heidi. For Trump, only cosmetic things matter. A pitiable person.

(7) Fraud vs (10) F**kface

(7) Fraud

With a couple weeks to go before Election Day, and with nothing even approximating adequate evidence, Donald Trump asserts that our main democratic institution—our electoral system—has been illegally captured by Democrats. One of Trump’s very worst features is his willingness to burn our institutions to the ground if he can extract even the most minuscule personal advantage from doing so.

(10) F**kface

This tweet, from the future president of the United States, includes the term “F**kface Von Clownstick.” That is all.

(2) Trump U vs (15) Affleck

(2) Trump U

So, Trump U is one of the most shameless grifts to ever come out in the “educational” space (using that word extremely loosely)—and, man, the educational sector has seen some grifts. What makes this tweet extra offensive is that this man’s entire being is a Trump Tower-sized middle finger raised against the very idea that genuine learning matters. Go ahead and scam people with Trump Steaks or whatever. But you don’t get to scam people within higher learning. That’s just cosmically wrong for you of all people to get to do that.

(15) Affleck



(1) Vaccines vs (16) Manziel

(1) Vaccines

There is so much wrong with this tweet. There’s the faux narrative structure (“Healthy young child goes to doctor…”). There’s the idea that the “healthy young child” first “doesn’t feel good” and then “changes.” Very helpful description of the developmental path there. And then there’s the all-caps “AUTISM” waiting in the explanatory wings, ready to provide a scientifically solid account of this medical conundrum. Finally, there’s the HARD DATA that Trump provides at the end by reference to “many such cases.” What a tweet.



(8) Alaska vs (9) Hoax

(8) Alaska


(9) Hoax

“It is snowing, therefore global warming is a hoax” is a take that explodes in your face like a logic bomb and now your brain is splattered on the pavement.

(5) Games vs (12) HuffPost

(5) Games

Obviously the worst part of this tweet is the baseless suggestion that video games “create monsters.” But an underrated fail here is Trump’s clumsy insertion of “glorification.” The idea in these debates is that video games contain the glorification of violence. But Trump instead phrases it as “video game violence & glorification,” which, if you remove “violence,” reads like Trump is saying “video game glorification” is creating monsters. Who knew that thinking Animal Crossing is great has such a pernicious effect! Stop glorifying video games, people.


This guy cares so very much about looks. Which is weird, because, apart from money I’m not so sure that he’d be crushing the dating scene. This tweet is a vicious attack. Plus, why the reference to her ex husband leaving her “for a man”? Why is that important?

(4) Birther vs (13) Obama

(4) Birther

This posture—never apologize; always “take the offensive”—is simultaneously one of the things his supporters most like about Trump (“he fights!”) and one of the worst things about him.

(13) Obama

Part of Trump’s relentlessly racist Obama smear campaign.

(6) Schlonged vs (11) Gloomy

(6) Schlonged

Cards on the table: “schlonged” is a masterful word. It truly is a marvel of the language. Which is why Trump’s decision to downplay its true meaning is such a betrayal. It clearly doesn’t mean beating someone badly. What’s weird is that Trump says all kinds of unhinged stuff but this—THIS—is something he feels he has to walk back?

(11) Gloomy

Can you fathom the level of self-importance necessary to unironically type out the words “The world was gloomy before I won”?

(3) Landslide vs (14) Jonah

(3) Landslide

There are two egregious falsehoods here: (1) that Trump won “in a landslide” and (2) that millions of people “voted illegally.” Trump is among the best in the entire Twitter universe at jam-packing, just consolidating, lies and falsehoods within single tweets.

(14) Jonah

There is so much going on here. First, there’s Trump quoting a hilarious insult at his own expense. Anytime you’re quoting verbatim someone roasting you, it’s like an extra opportunity for people to laugh at you (“Bro, you said the other day that my ‘breath is so bad it causes flowers to instantaneously wilt and that I am the greatest loser in the history of loserdom.’ I didn’t like that you said that.”). Then, there’s the suggestion that Trump being likened to 14 year old girls is a “horrible insult to women.” Why, bud, because they’d be so insulted to be compared to you? But it ends in an amicable way as Trump helpfully provides Jonah Goldberg with the opportunity to pick when he will resign. Look, he doesn’t have to do it now. He can do it later. It’s cool. Whatevs.

(7) Athlete vs (10) Haters

(7) Athlete

Since learning of this tweet, I’ve thought about Coach Ted Dobias quite a bit. I’ve thought about what his life must have been like to not exist at all, because there is zero chance Trump played sports at all, let alone that he was the best in New York at any sport other than receiving a hefty inheritance from dad.

(10) Haters

The love and affection oozes out of this man as he delicately whispers the following sweet nothing into our collective ears: “I cannot help the fact that you were born fucked up!”

(2) Lightbulbs vs (15) Carson

(2) Lightbulbs

Cancer-causing lightbulbs. You hate to see it.

(15) Carson

Donald Trump running through a list of Ben Carson’s most hilarious confessions is actually quite great. Carson, like Trump, is a remarkable person, combining violent tendencies with a joyous freedom to theorize freely in the realm of pyramid studies.


(1) Corona vs (16) Liddle

(1) Corona

This tweet, more than any other, reveals the motivating force behind Trump’s catastrophic negligence in the face of a looming pandemic. He wanted the stock market to remain strong. His number one pitch to the American people, heading into the elections, was: Look at our amazing economy! Taking an aggressive stance against the coronavirus would have complicated that, likely causing stock prices to crash. Absolutely unforgivable.

(16) Liddle

Bro what in the hell

(8) Kansas vs (9) Christmas

(8) Kansas

So, this is a first in this tournament. This one is a deleted tweet. I partially defended Trump when this first came out, because it’s not obvious that a town called “Kansas City” is going to be anywhere but in Kansas. Why, then, does this tweet make the cut? Because Trump has styled himself the great oracle of the American heartland. Can’t do that while at the same time not knowing basic things about the Midwest.

(9) Christmas

There is no dumber war in the history of wars than the War on Christmas. And, folks, the human race has had some dumb wars.

(5) Treason vs (12) Elijah

(5) Treason

Donald Trump, the president of the United States, actually tweeted out that a political opponent of his should be tried for treason. How unhinged is this?

(12) Elijah

This tweet belongs to a multi-tweet saga in which Trump repeatedly singled out Elijah Cummings and the city of Baltimore for being emblematic of everything he—and, crucially, his supporters—despise about America. The empathy emanating from Trump’s “Too bad!” is palpable.

(4) Tapp vs (13) 400

(4) Tapp

This tweet contains many quintessentially Trumpian features. A bizarre misspelling (“tapp”), an over the top description of something to try to make the target person look worse for what they’ve done (“very sacred election process”), a historically illiterate comparison (What Obama did vs. Watergate), an outlandish insult (“Bad (or sick) guy”), and, finally, an unnecessary use of parentheses (“(or sick)”). Ticks all the Bad Tweet boxes.

(13) 400

There it is. There’s the reference to our 400 pound hacker. This is the closest we’ve come to figuring out what image enters Trump mind when he thinks about who hackers are and what kind of bodily shape they are in.

(6) Nunes vs (11) Peepers

(6) Nunes

Never has a man of such blinding unimportance, of such little talent, been exalted like this. This should be hagiographic satire, but it’s somehow real.

(11) Peepers

Honestly couldn’t stop laughing at this tweet. The “it’s not true!” bit is so funny because this is clearly motivated by wanting very badly to publicly call these people these names but this was the only way he could do so. I mean, that’s the structure here. He’s saying: “these people say I call this guy Mr. Magoo and this other guy Mr. Peepers but it’s not true!” And the whole point is to put out there the Magoo and Peepers bit.

(3) Russia vs (14) Religion

(3) Russia

It is simply unreal what Trump tries to get away with. Imagine being Donald Trump and trying to suggest Russia wants anyone but you in the Oval.

(14) Religion

I hope Jesus is taking notes. Because he’s been one-upped by this savior of religion.

(7) Impeached vs (10) Coup

(7) Impeached

One of the funniest things to come out of the whole impeachment saga is the way Trump insisted on describing his phone call with the Ukrainian president. He kept characterizing it as a “perfect” phone call. That’s just a weird way to put it. Like, “perfectly legal makes sense. Honestly the all-caps flourish and the substance of what he’s saying, a hysterical incredulity over getting impeached because of a phone call, makes this an instant classic.

(10) Coup

This deserves to be in here for the decision to use “coup,” alone. Anyone who has ever read anything about coups knows the Russia investigation was not a coup.

(2) Witch Hunt vs (15) Apple

(2) Witch Hunt

Let’s do the math here. Trump enduring opposition from Democrats is a harsher treatment than Abraham Lincoln getting assassinated. Verdict: totally checks out.

(15) Apple

Has there ever been a better explanation for any misstep, in the grand history of missteps, than this? Trump is suggesting he was using a linguistic shortcut, a “way to save time and words,” when he called Tim Cook, CEO of Apple, “Tim Apple.” You love to see such a commitment to being economical with language. Perhaps a love of poetry taught him this skill.


(1) Virus vs (16) Crowley

(1) Virus

One of the biggest lies on display in this entire tournament—itself a monumental achievement—is “I always treated the Chinese Virus very seriously.” Let’s see, failing to act on warnings given to you months in advance and then shepherding the country into top honors for global coronavirus cases and deaths is absolutely representative of taking the virus “very seriously.”

(16) Crowley

What makes this tweet so funny is that this is a reference to the emergence of AOC, who beat the powerful Democrat Joe Crowley to take her seat in the House. What’s funny about that? Trump seems to think Crowley being critical of Trump is what did him in. Yes, because if there’s anything that mobilizes Democratic Socialists to get the vote out is politicians who are insufficiently respectful to Donald Trump.

(8) Turkey vs (9) Mars

(8) Turkey

The money quote is: “in my great and unmatched wisdom.” How do you write that unironically? How does a person come to have such dizzyingly absurd levels of self-regard?

(9) Mars

The moon is not a part of Mars lmao

(5) Liberate vs (12) Wall

(5) Liberate

Only time in this tournament in which I stacked multiple tweets together. Because, really, they’re the same sentiment. The sheer irresponsibility of posting this is unreal.

(12) Wall

Trump is trying to act like the USMCA, the follow-up to NAFTA, is a fulfillment of his outlandish campaign promise to have Mexico pay for his wall. Imagine thinking that all the people chanting that Mexico will pay for the wall during Trump’s rallies in 2015–2016 had a NAFTA-like agreement as the mechanism by which they envisioned Trump would fulfill this campaign promise. Absurd.

(4) Covfefe vs (13) Writer

(4) Covfefe

The second deleted tweet entry in this tournament. An instant classic. As dependable as instant covfefe.

(13) Writer

I love how he qualifies the obviously absurd “priding myself on my ability to write” with “somewhat.” Isn’t it common knowledge that Trump didn’t write his own books? What is he talking about?

(6) Hydro vs (11) Rocket

(6) Hydro

Game changer.

(11) Rocket

Cringe level is off the charts here. “North Korea will become a different kind of Rocket — an Economic one!” LOL

(3) Steal vs (14) Lynch

(3) Steal

So irresponsible. So over the top. So bad.

(14) Lynch

Yes, impeachment is equivalent to a lynching. This right here is why #Blexit is such a powerful social movement.

(7) Shadow vs (10) Love

(7) Shadow

Did you know that Arch Conservative Constitutionalist Donald J. Trump thinks it’s illegal for a private company to restrict the visibility of certain users?

(10) Love

Saying that rival politicians are “incapable of loving our country” is reprehensible.

(2) License vs (15) Noble

(2) License

Oh, nothing. Just the president calling for media entities to be censored. No big deal.

(15) Noble

This is a new one. But already a classic. Trump misspelled “Nobel” as “Noble” (first of all, what he actually wanted to say was “Pulitzer”—so there are, like, layers of mistakes going on here), and then didn’t have the integrity to admit he was wrong. So he came out with this beauty. He blamed on “sarcasm.” You love to see it.


(1) Kenya vs (8) Barney

(5) Autism vs (13) Groveling

(11) Mosque vs (14) Cruz

(2) Trump U vs (10) F**kface


(1) Vaccines vs (9) Hoax

(4) Birther vs (12) HuffPost

(6) Schlonged vs (14) Jonah

(2) Lightbulbs vs (7) Athlete


(1) Corona vs (9) Christmas

(4) Tapp vs (5) Treason

(11) Peepers vs (14) Religion

(2) Witch Hunt vs (7) Impeached


(1) Virus vs (8) Turkey

(4) Covfefe vs (5) Liberate

(11) Rocket vs (14) Lynch

(10) Love vs (15) Noble


(1) Kenya vs (5) Autism

(10) F**kface vs (14) Cruz


(1) Vaccines vs (4) Birther

(2) Lightbulbs vs (6) Schlonged


(1) Corona vs (5) Treason

(7) Impeached vs (14) Religion


(4) Covfefe vs (8) Turkey

(14) Lynch vs (15) Noble


(5) Autism vs (10) F**kface


(1) Vaccines vs (6) Schlonged


(1) Corona vs (7) Impeached


(8) Turkey vs (15) Noble


(1) Corona vs (5) Autism

(1) Vaccines vs (8) Turkey


(1) Corona vs (8) Turkey

… and the winner is …

(8) Turkey!

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