Trump Meme Mastermind Brenden Dilley Talks MAGA, DeSantis

DES MOINES, Iowa — It may have been 4 below zero outside the glass doors of the Iowa Event Center, but Brenden Dilley wasn’t letting a little thing like potential frostbite diminish his enjoyment of a good cigar.

Inside, several hundred of his friends and like-minded associates were drinking in former President Donald Trump’s big night in the Republican Iowa caucuses, cheering wildly as a big board depicting the state of Iowa showed one county after another falling in line for their candidate.

But when the Associated Press, Fox News, CNN and MSNBC all called the race at about 7:30 p.m. local time — just a half hour after voting at caucus sites across the state had begun — Dilley made for the door, deciding the time had come to truly savor the moment.

A superstar in Trump world and a one-time congressional candidate in the state of Arizona, Dilley is a podcaster and the driving force behind a meme army that faithfully lionizes Trump at every opportunity while brutally eviscerating his opponents.

Trump himself is said to love their guerrilla messaging efforts, so much so that he featured their “Let’s Get Ready to Bumble,” a savage putdown of President Joe Biden, at several of his rallies last year.

The group is also widely credited with making Florida Gov. Ron DeSantis’s footwear a minor obsession in the mainstream media.

Beginning with simply mocking DeSantis’s decision to wear unmanly white galoshes to a hurricane-related press conference, the group’s members more recently have been gleefully pushing “bootgate,” the as-yet unverified rumor the governor wears lifts in his cowboy boots.

“Why are we here?” Dilley asked, repeating a question from a passerby as he and one of his content developers enjoyed their cigars.

“Two reasons,” he said. “One is to support our president; the other is to destroy Ron DeSantis, forever.”

Dilley had flown in from Georgia to be on hand for caucus night. His content maker, who politely declined to give his name since most meme-makers post anonymously, had traveled even farther, having flown in from Los Angeles.

“You know the ‘God made Trump’ meme? Our team made that,” Dilley said proudly. “Have you seen memes of DeSantis picking his nose? Well, we made those too.”

“The New York Times recently called us ‘Trump’s online war machine,’” the content designer said.

“Yeah,” Dilley said. “That’s how they branded us. Now everybody is calling us that.”

Critics of the Dilley Meme Team’s two dozen members paint them as villains who traffic freely in misinformation, exaggeration, deepfakes and unleashed artificial intelligence.

Fans, particularly on the right, embrace their unapologetically ribald humor and sticking-it-to-the-PC-police mentality.

Whichever side one is on, the undeniable fact is that in an age when social media is a prime mover of political content, their work has become as much a part of the conversation as traditional political advertising.

Dilley, as affable and friendly a man as could be, continued to explain why someone would fly from the relative warmth of the Deep South to a city — Des Moines — that was still reeling from a blizzard that passed through the day before.

“We came out here to support the president,” he said. “And, you know, we wanted to be here. We wanted to be here in person to see it all the way through.

“We started our mission about a year ago, not just to get Trump reelected, but also, once it became obvious what DeSantis was going to do, to kneecap him forever,” he said.

Dilley then explained his unrestrained disdain for Florida’s governor.

“The bottom line is it’s about betrayal,” he said. “Everybody thinks it’s about his betraying Trump, which it is to a large degree, but you have to remember, he also betrayed all of the voters in Florida — and a lot of our team members are in Florida.

“They loved [DeSantis]. We helped him get reelected. And then once he got reelected, he immediately went on this bogus book tour which everyone knew was a soft-launch of a political campaign, even while he was claiming it wasn’t,” he said.

“Now, there was a way he could have done this … he could have just come out and said, ‘Look, I know you just got me reelected to another term as governor, and I know I told Trump I wouldn’t run against him, but I’m concerned because of X, Y and Z … and while I still support Trump, I want to be here in the event something happens.

“If that had been the case, I probably wouldn’t have been as angry,” Dilley said. “But [DeSantis] came out and he completely spit in the eye of everybody who voted for him and who were also Trump supporters,” Dilley said. “The only reason he was elected governor in the first place was because Trump endorsed him. I mean, the guy did commercials with his children wearing MAGA onesies.

“I mean, the situation is … infuriating, but also awkward,” he continued. “Because you really have people like me wondering, ‘Well, were you being an idiot then, when we supported you, saying nice things about Trump to get his endorsement? Or are you being an idiot now, saying Trump’s not fit for office, merely because you want the job yourself?’

“Either way, it was kinda’ gross, and I’ve thoroughly enjoyed destroying him,” Dilley said.

Just the night before, the DeSantis campaign inadvertently handed Dilley and cohorts a bit more ammunition when it allegedly had a man in a wheelchair ejected from a campaign event for wearing a Dilley Team baseball cap.

“He was in a wheelchair … and they dragged him out because they assumed that anyone who would wear my hat had to be there to disrupt the event,” Dilley said. “I don’t know this guy. He’s a fan … who also happened to be an undecided voter. He was there to listen, and instead, it went very badly.

“But that’s the thing about DeSantis: Every time we even consider letting off the pedal on this guy, he does something that makes you say, ‘Okay, let’s finish him.’”

Dilley was asked why he and his team don’t appear to have the same level of animus toward former South Carolina Gov. Nikki Haley, who was Trump’s U.N. ambassador.

“The fact of the matter is, I think she’s irrelevant,” he explained. “I think she’s got a ceiling of probably 19 to 22 points. And I admit, there are voters who’ll say, ‘I really like this or that about her and I support her,’ but there just aren’t enough of them to make her a legitimate threat.

“At the same time, I also believe that she’s a prop, a front for the never-Trumpers,” he said. “I think a lot of people, a lot of Democrats, are pouring money into Haley’s campaign so she can stay in the race, forcing Trump to eat up his resources before the general election and preventing him from turning his attention to Biden full time.

“It’s a hell of a strategy, but it isn’t going to work,” he said.

By the time Dilley and his California-based meme maker were ready to turn their attention squarely back to their cigars, Trump’s margin of victory in Iowa was guaranteed to smash the previous record for a Republican presidential candidate.

In the end, Trump won the support of 51% of Iowa caucusgoers, a 30-point victory over DeSantis, who came in second place with 21% of support. Haley won 19% to come in third.

With the night almost over, attention immediately turned to the future, a fraught subject when it comes to Trump, who faces 91 felony counts in four criminal cases in Washington, New York, Florida and Georgia.

Dilley spoke for many in Trump’s world by dismissing the cases as “bunk.”

“I have total faith that Trump is going to prevail in all these cases,” he said. “I think the evidence is preposterous … and I think a number of the things the authorities are asking us to believe … are just insulting.

“The thing about the perception of power is that it’s derived from fear, right? And it’s predicated on me buying your bulls—, you know? Trump’s not going to cave to that, and frankly, I’m not too worried about how these cases will play out,” he said.

As for the next key primary states, Dilley said he was certain Trump would prevail in them as well.

“He’s going to win in New Hampshire. I have no doubt about that, and I think it’s going to be by another 20-point or so margin, although we could see a lot of independent voters who lean left, vote in the primary and that could skew the outcome, making it a little closer,” he said. “From there it’s on to South Carolina, which he’ll win … where I think he’s going to embarrass Nikki Haley.”

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