My Brief Time As Donald Trump's Campaign Manager

To do over again, sure, I probably wouldn't have helped Donald Trump run for president.
My Brief Time As Donald Trump's Campaign Manager

To do over again, sure, I probably wouldn't have helped Donald Trump run for president.

In my defense, you have to understand one thing: When we started, we never meant to take it this far. We didn't want any of this to happen. Honestly.

I know that must sound impossible now, with Donald leading the GOP and absolutely dominating the media landscape, but, once upon a time, this was supposed to be a joke.

I should start at the beginning.

My Brief Time As Donald Trump's Campaign Manager
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No, not that part.

The Beginning

Donald first reached out to me a year ago because he liked my book, How To Fight Presidents, which was really no surprise to me. Ego is a huge part of that book, and Donald -- the real Donald, that I know -- has privately described himself as "a student of ego." He's always been fascinated with the idea of deluded, larger-than-life characters, people who make living legends of themselves. He emailed me saying he enjoyed the book, an email turned into a text conversation, which turned into a phone call, and before I knew it, I was meeting Donald Trump for lunch every week.

Talking about the book got us talking about the time the Secret Service interrogated me while working on the book (the short version is that, while researching, I wrote a satire article on Cracked that might have been considered "vaguely threatening" to the president, then the Secret Service made us take the article down, and then the Secret Service interviewed me to make sure I wasn't a terrorist ). Donald loved that story, and since we'd gotten pretty close at this point, I told Donald something that I hadn't admitted to anyone else before.

"When I was working on that book and simultaneously writing articles that I knew could be generously described as 'lightheartedly treasonous,'" I said, "in the back of my mind, I kind of hoped the Secret Service would contact and subsequently interrogate me. I wouldn't say I was baiting them, necessarily, but somewhere deep down I knew it was a possibility and I thought, 'Man, if the Secret Service contacts me and hassles me over this, I bet I could get a great article out of it.' I try to do stuff like that a lot, with jokes and comedy and ... stuff."

Donald thought for a moment. "Expand on that," he said. As much as he loved business, he was also fascinated with comedy and process and entertainment in general.

My Brief Time As Donald Trump's Campaign Manager

You may recall the famous satire books he's released over the years.

"Well, sometimes in comedy -- for me, anyway -- the real joke comes after; it comes in the reaction, you know? You make one joke, but the real joke, the better and purer joke, is what your joke causes, or what it inevitably leads to. I wrote one article that was a satirical guide to committing a crime against the sitting president, and it was a funny enough article, but getting interrogated by the Secret Service? That's the actual goal, 'cause that's real, and you can't really script something like that. I guess it's like ... catching a fish and then using that fish as bait to catch a bigger, better fish? That's kind of a clumsy way of explaining it, but-"

"No," Donald said in an attempt to interrupt me.

"So maybe imagine you caught a small fish and you were like, 'Fish are fine, but wouldn't it be cooler if there was a monkey that ate fish?' and then you catch the monkey and the monkey is ... the Secret Service?"

"Stop it, Daniel, I get it. I get you. And you know what?"

I didn't say anything, because I didn't know what, and I didn't want to say, "No, what?" because I think rhetorical exercises like that are a waste of time and boring. He took a long drag off the joint we'd been passing back and forth (Full Disclosure: We'd been passing a joint back and forth this whole time).

"I'm gonna run for fucking president." Big exhale.

My Brief Time As Donald Trump's Campaign Manager
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Big. Yuge.

It didn't take me more than 10 seconds to realize that this would be the single greatest piece of comedic performance art since Andy Kaufman.

"You're gonna run for fucking president."

"I'm gonna run for a few months as a real-life, honest-to-God Internet troll incarnate. I'm gonna cause a big stir, get a shitload of media coverage, and trick the entire country into thinking a loud, offensive, dumb clown could seriously run for president."

"You're going to 'Borat' the whole country."

"I'm gonna 'Borat' the whole country. And when they kick me out of the race, I'm gonna reveal it was all a big prank. This is going to be so funny."

"This is going to be so funny."

And that's how I became Donald Trump's campaign manager. We thought we'd be at this for two months, tops.

On Being Donald Trump

Inventing the character of "Donald Trump: Presidential Candidate" wasn't easy. I mean, what we ultimately settled on (Jingoistic, Racist Bully) seems obvious in retrospect, but we workshopped a lot of ideas that ultimately went nowhere.

We considered going full Borat and making the Trump character seem vaguely foreign and snotty about America, because it's one of the tactics that the WWE uses when they want you to instantly hate a wrestler, but we abandoned that because Donald sucks at literally every accent (his impression of a French person might actually be a war crime).

We settled on a cocktail that was one part Vince McMahon, two parts "rich '80s bully" archetype, one part racist uncle, and just a splash of Hitler.

My Brief Time As Donald Trump's Campaign Manager
The Telegraph

No, not that part ... I think ...

We came up with a series of campaign promises that ran the gamut from impossible to legitimately insulting (and in some fun cases, both!) and decided to meet every form of criticism with blind, misguided aggression. His platform was almost too easy. "I'm the best and you're all losers and women are weak." We weren't reinventing the wheel or anything; we were essentially doing exactly what Andy Kaufman did when he pretended to be a professional wrestler.

We kicked around a LOT of good, dumb slogans before settling on "Make America Great Again." I really wanted to go with "America: Put It In You," but Donald thought it would be too obvious and no one would take us seriously. We laughed at "Donald Trump: Making America The Biggest Country In The World (Again)," but it felt a little clunky and too on-the-nose. "You Can't Spell America Without ME" was a strong early contender, and I was so excited about the barely concealed racism of "Trump: One Of Us" that I still have a bunch of hats with that slogan on it.

My Brief Time As Donald Trump's Campaign Manager

Make me an offer.

But "Make America Great Again" was a good choice. We wanted something that felt like a pleasant-sounding but ultimately empty promise while still carrying the vague sense of "good ole days" racism. The kind of slogan that made less sense the more you repeated it.

"Make America Great Again," Donald said out loud when he first put his now-infamous red cap on. "Doesn't even make any sense. If anything, I'm worried people will be able to tell it's a bit right off the bat and we won't even get a chance to debate."

"This is gonna be so funny," I said.

In hindsight, maybe we were too subtle.

On Meeting The Other Candidates

The first debate was a blast. We all got together for a pre-debate meal, and Donald and I couldn't stop laughing, because all of the other candidates took this so seriously and even they couldn't tell that we were just fucking around. And some of the candidates were all right. The tiny Men In Black alien inside Rubio's face is actually a good dude, and I think Dr. Carson is goddamn adorable and maybe the only other person there who was actually having a good time. Some people think Chris Christie is nice, but I'm from Jersey, so I know what he's actually like (bad!). Kasich clearly just needs a hobby and thought running for president might do it (I suggested model trains). Jeb Bush was there. Cruz, on the other hand, rubbed us both the wrong way. It was hard sitting through a meal with him and Donald, and I couldn't talk about anything else on our drive home after the debate.

Erich Schlegel/Getty Images News/Getty Images

Now imagine him eating ribs. It's the worst, right

"Ted Cruz looks like he would run a toy store in a Twilight Zone episode about a toy store that lures in children with promises of cool gifts and then turns the children into toys, forever," I said.

Donald said, "He looks like he could be Pee-wee Herman's long-lost brother who grew up shitty because he ended up with a lot of money, but still dresses weird and doesn't know how to interact with real humans because he has that weird social brokenness common to all men in the Herman family."

"Ted Cruz looks like he would try to shut down the Ghostbusters."

"Have you ever Googled 'Young Ted Cruz'? It's just a bunch of pictures of whatever is in between tadpole and adult frog in the life-cycle of a frog."

"I Googled 'Ted Cruz Shirtless' and the FBI showed up and arrested my computer for 'sex hate.'"

"The doctor who delivered Ted Cruz is a friend of mine, a good friend, and he said when they did the ultrasound to find out what the sex was when Ted was still in the womb, the only thing they could come up with was 'wrong.'"

"One time while he was asleep I dropped a pebble onto his dewlap, that neck-fat area of his, and I watched the skin just ripple and ripple and ripple."

"That sounds very zen-like."

"It was; I got a lot of thinking done, achieved inner peace."

My Brief Time As Donald Trump's Campaign Manager
jinga80/iStock/Getty Images

"Ted Cruz once told me he was so mad all the time because his penis is 'an innie.' I begged him not to show me, but ..."

"Sure. Watch the next time Ted Cruz's two little girls are on camera; no matter what they're saying, their eyes are blinking. 'We're not his' in Morse Code, over and over again."

"You know how there was always that one kid in class who would remind the teacher that she forgot to give out homework?"


"Well Ted Cruz looks like a piece of shit."

We went on like this for some time. This was back when we were still having fun on the campaign. Before ...

My Brief Time As Donald Trump's Campaign Manager

On "The Wall Thing"

You have to believe me: Promising to build a wall was supposed to be the thing that let everyone else know that we weren't serious about running. A giant wall between Mexico and America? That's a child's idea of national security, a dumb child. All of Trump's other promises were just kind of empty and superficially stupid. "More money and jobs for everyone, a gun in every stroller, the best words" -- that's the kind platform you run on when you're campaigning for president of the eighth grade; it's just pandering, nice-sounding bullshit you have no intention of accomplishing.

My Brief Time As Donald Trump's Campaign Manager
Alex Wong/Getty Images News/Getty Images

"All of my words are just so good you guys."

But the wall bit? That was supposed to be our signal to let the country know that our best idea is something a dumb child would come up with. We were so certain that the wall would crash and burn Donald's campaign that I'd actually booked a cruise for us to go on together and scheduled it for the day after Donald was going to announce his whole, stupid, wildly offensive wall plan. I was already in my bathing suit and pouring whiskey into an emptied bottle of suntan lotion (they don't let you bring your own bottles of alcohol onto a cruise, but they can't tell if you sneak it in bottles of sunscreen or shampoo or whatever, LIFE HACK) when Donald called me.

"You're not gonna believe this," Donald said.

"I probably will, actually -- I would believe almost anything after a person says, 'You're not gonna believe this.' Doesn't everybody? Who wouldn't? 'Cause I'm already expecting to hear something that sounds hard-to-believe so, like, I'm prepped for it."

"Daniel! The wall thing killed."

"Shut the fuck up."

"Killed! I'm still in the race. The wall thing killed."

"That's insane! Who would think that's a good idea?" I asked.

"Fuckin' America, man, I don't know; I'm really freakin' out here."

"This is fine," I said calmly, "I can fix this. We'll just come up with some crazier, more ridiculous stuff; this will all be over soon, you'll see."

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Joe Raedle/Getty Images News/Getty Images

I hung up and poured myself a double SPF 15 on the rocks.

As you know now, things just got worse from there. Every xenophobic thing we made the Trump character say was just met with more cheers. Every act of schoolyard bullying made him seem stronger. I gave him very specific training on how to talk for minutes at a time without actually saying anything, which is a really impressive skill if you think about it, but no matter what he said, the media would just come out and say, "Love him or hate him, Trump speaks his mind!"

Our weekly lunches were eventually replaced with daily campaign strategy meetings, interviews with legitimate news sources, and constant rallies.

"I promise to make the trains run on time," Trump shouted to a sold-out crowd at a Nevada rally that may or may not have known that he was directly comparing himself to Mussolini. They went apeshit for it. We both smiled and waved at the enormous crowd of some of the most passionate maniacs I've ever seen.

"This is fucked," Donald whispered to me through his smile.

"This is fucked," I agreed.

At this point, I didn't even know what to do anymore. I briefly flirted with the idea of having Donald flat-out use the N-word in a rally, but if I'm being honest, I was terrified to find out if that would actually help his numbers. He publicly admitted that he could shoot someone on the street and it didn't make a dent in his campaign.

I still held out some slim hope that everyone would regain their senses, catch on, and kick us out of the race. But then ... Chris fucking Christie.

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Scott Olson/Getty Images News/Getty Images

Bob's Fuck Boi.

On Chris Fucking Christie

Letting New Jersey Governor and frowning ham in a suit Chris Christie in on the joke was, in hindsight, a mistake. After he'd dropped out of the race, Donald and I took Christie out for a few drinks at a classy little bar called The Wellesbourne in West Los Angeles. I got an old fashioned, Donald got a gin martini, and Christie got what he called "The Governor's Special" (it's a half cup of vodka poured into a quart of milkshake he brought from home).

Remember, we were exhausted at this point. What was supposed to be a fun little comedy bit turned into a full-time job that had us traveling all over the country. After a while, it gets hard to keep up appearances, especially for Donald, who found playing the Trump character to be disgusting and physically very draining. We never wanted to tell anyone what our plan was, but we'd had a few drinks, we were already so tired, and our defenses were down. We ended up telling Christie everything.

"Let me get this straight," he said, "you don't actually want to be president?"

"Of course not," Donald said, "I'm just doin' a -- whaddaya call it -- like what Joaquin Phoenix did a couple of years ago. Remember?"

"Yes, everyone hated that," Christie said between handfuls of french fries. He had a sack of french fries, he was eating french fries out of a sack.

My Brief Time As Donald Trump's Campaign Manager
ManuHK/iStock/Getty Images

We could both tell he was waiting for us to look away so he could mix the fries
into his Governor's Special.

"This is different," I explained. "Joaquin was just doing some weird, self-indulgent, actor thing. Donald is making a statement about modern politics, celebrity culture, the -- Governor Christie, please close your mouth when you chew; this is a nice bar -- the toxicity of narcissism, and just our culture in general. Once he reveals that he's not actually running, I really feel like it'll be a game-changer for comedy. It, uh ... has gone on a little longer than either of us expected."

"GOD, I can't wait for this to be over," Trump said, "but the longer it goes on, the funnier it'll eventually be." I nodded. Christie reflexively laughed the way a child laughs when it pretends it understands a grown-up's joke.

"Oh, yeah, I get it now. That's real funny."

We had a few more drinks, had a few laughs, got really sad watching Christie get in an argument with a 7-Eleven employee by insisting that there's supposed to be a price break if you order four hot dogs, and then laughed real hard again when he inevitably dropped all four of them on his way out of the store. We told Christie not to tell anyone that Trump was running as a goof, and we strongly suggested that he not pick up the hot dogs, and then we went our separate ways.

Twenty-four hours later, Chris Christie endorsed Donald Trump for president. I barged into Christie's stupid office.

Justin Sullivan/Getty Images News/Getty Images

His staff told me he was in the back.

"Christie, what the fuck are you doing?"

"What," Christie said, "I'm playing along; I'm doing what you guys do. I'm part of the bit now."

"No, Christie, you sweaty, potato-headed shitbox Cowboy's fan idiot, you're not."

"Yes I am, I'm endorsing Trump. You know, as a joke."

"But no one else is going to see it that way -- they're just going to think an establishment-lane Republican is legitimately endorsing a maniac. Jesus, not everyone can just jump into a bit."

I called Donald. It went straight to voicemail.

"Donald, it's me; I'm sure you saw the news. It's fine, this is fine, I'm gonna fix this, stay where you are."

"What can I do," Christie asked.

"I don't know. Nothing. Shut up, Rock Monster from NeverEnding Story -- you've done enough."

I texted Donald and said, "I got this," but, honestly, I didn't know. I just didn't know.


You already know what happened. Super Tuesday came and went, and Donald Trump, my friend and partner in comedy, is all but guaranteed to be the fucking nominee for the Republican fucking Party, and I'm his fucking campaign manager.

My Brief Time As Donald Trump's Campaign Manager

At least I can say that, in our quest to get Trump kicked out of this race, we tried everything. We looked at people who have historically screwed up in a big, public way and tried to do what they did. People got mad when John Lennon said The Beatles were bigger than Jesus, so I had Trump call out the pope. We called almost everyone in another country rapists and thieves, we promised an impossible-on-all-levels wall, we bullied minorities, and made fun of women; we basically taught a class on how you SHOULDN'T run a campaign, but it still worked out. Having Donald accidentally accept the endorsement of the KKK was, I thought, my masterstroke, but even that didn't slow down his momentum. Reality.


It's 11:55 p.m. on a Thursday. I'm sitting across from Donald in a secluded corner of some party celebrating his eventual nomination. He looks a hundred years older than when I first met him a year ago. His hands, small hands, they've always been small, are shaking. We have to catch an early flight to Ohio for some speaking engagement before heading off to Los Angeles for a book signing, then Washington for Meet The Press. Or maybe the speaking engagement is in L.A. and the signing is in Ohio. It's so hard to keep track anymore. In my defense, I was never supposed to be a campaign manager. Donald grabs my arm. His grip is weak.

"This'll be funny, right Daniel? When they eventually -- when Jon Stewart or someone comes out and exposes what a fraud I am, and the country starts making sense again, it'll be funny, right? Right?"

"That's right, Donald."

"I'm not gonna have to be president, right?"

"Of course not, Donald."

"OK. Tell me again, Daniel. Tell me the story about the Secret Service. About how you were scared at first but then everything worked out in the end, and now we can laugh about it."

"You got it, Donald. You got it."


Daniel O'Brien is the Creative Director for Cracked and author of How To Fight Presidents and the upcoming children's book Your Presidential Fantasy Dream Team, which is available for preorder. He also hosts a podcast about presidents called Dead Presidents (with special guests including Golden Globe-winner Rachel Bloom and Fall Out Boy's Patrick Stump), which you can get here!

Find more of Dan O'Brien's adventures through time, space, and insanity when you read My Brief Time As Iron Man's Sidekick and read as Dan drunkenly stumbles his way through the wizarding world in My Brief Time as a Student at Hogwarts.

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