David Litt left the White House in 2016 as a special assistant to the president and senior presidential speechwriter. He is currently the head writer/producer for Funny or Die.

As President Obama’s second term began, many top advisers, their personal legacies cemented and a second term secure, were finally ready to leave. David Plouffe, the electoral mastermind. Deputy Chief of Staff Nancy-Ann DeParle, who stewarded the president’s health care law. David Axelrod, who shaped the Obama vision more than anyone except Obama himself. And Favs. At just 31 years old, Jon Favreau was already an accomplished speechwriter. With no new rhetorical worlds to conquer, he left in early 2013. I was sad to see Favs go. He was a good boss and a remarkable talent.

But President Obama’s loss was my gain—the chief wordsmith’s departure left an opening at the bottom of the speechwriting totem pole. When I returned to the White House in March 2013 after writing speeches for the re-election campaign, my days of professional promiscuity (writing for senior advisor Valerie Jarett, and also the chief of staff, and also the other senior staff, and also sometimes POTUS) were over.


At the top of the totem pole, Favs’s spot was filled by his deputy, Cody Keenan. It was a smooth transition: Cody had been writing speeches for POTUS since the first campaign, and knew the president well.

I was especially grateful for this during a POTUS meeting my first week back. The subject was the Gridiron Club Dinner, which, together with the Correspondents’ Dinner and the Alfalfa, makes up the Holy Trinity of presidential comedy events. As the token White House funny person, I was expected to take the lead on the speech. I told myself I wasn’t nervous. But when I reached the doorway I froze, terrified of doing something dumb.

Fortunately, Cody was completely comfortable. President Obama was seated behind his desk, an unread draft of the Gridiron remarks in his hand. My new boss sauntered toward him like a detective about to crack a case. I tiptoed cautiously behind.

“So,” POTUS asked, “are we funny?”

This was less a question than an invitation to make small talk. Cody didn’t miss a beat.

“Well, Litt’s pretty funny,” he said, nodding generously in my direction.

A brief hint of confusion crossed the president’s face. He clearly wasn’t sure he’d heard right. But after a moment’s pause, he decided to keep going.

“Yeah,” POTUS said. “Lips is funny.”

As you might imagine, I have replayed this moment frequently in my head. Perhaps I simply misheard the president. Perhaps time has warped my memory. But I don’t think so. I’m fairly certain Barack Obama called me Lips.

Here’s why I’m so sure. Number one, POTUS enjoyed banter. Going out of his way to extend pre-meeting small talk is exactly the sort of thing he would do. Second, while I wish I could say otherwise, President Obama had no reason to know my name. I’d written scripts for tapings. I’d helped him with the 2012 Correspondents’ Dinner. But lots of people pop in and out of a president’s orbit each year. At most I was a familiar face, the barista at your local Starbucks, the robber who wasn’t Joe Pesci in Home Alone. And there was no way I was going to correct the leader of the free world as something as unimportant as what to call me.

So Lips it was. And to be honest, as I settled onto the couch in the Oval, I wasn’t embarrassed. I was thrilled. The president of the United States had referred to me by name! True, it wasn’t my name, but no need to get nitpicky. Besides, I liked having an alter ego. Litt was shy. Litt was timid. But Lips? Lips could be bold. Lips could be daring.

Lips didn’t give a fuck.

And now, Lips was discussing the Gridiron Dinner. In 1885, when the Gridiron Club was founded, most of its members were grouchy old print journalists. Today, they still are. At their annual spring meeting, guests wear white tie. Reporters don costumes and perform parody songs about the politicians they cover. Petits fours are eaten. The evening ends with a chorus of “Auld Lang Syne.” It’s a four-hour homage to what people did before TV.

While nothing compares to journalists in Elvis wigs singing “Block Barack Around the Clock” (this actually happened, in 2011), the evening’s real highlights are the guest speakers. By tradition there’s a Republican, a Democrat and, if the invitation is accepted, the president of the United States.

Like the rest of the program, these monologues are a throwback to a simpler time. Even the Gridiron’s motto—Singe, but Never Burn—is an artifact of a happier, pre-Internet age. The draft I had discussed with POTUS included such scintillating topics as “Budget Cuts,” “Press Conferences” and “Guys Named Gene.” I can’t say he laughed uproariously at any of the jokes. But he understood his audience. Pronouncing himself satisfied, he showed us to the door.

Even as Lips, my cockiness had limits. I never dreamed of executing the ultimate White House power move—grabbing an apple from the Oval Office coffee table on my way out the door. Still, as I left the meeting, there was brashness in my step. After leaving in 2012 for the re-election campaign, I had been back at the White House less than a week. Already, I was meeting with the president himself!

By the middle of the week the jokes were almost finished, and I turned to what we called “the serious close.” These are staples of humor speeches, two or three paragraphs of sincerity at the end of otherwise lighthearted remarks. Since the audience was full of reporters, I took the occasion to praise journalists who embodied the best of the free press.

“They’ve risked everything to bring us stories from places like Syria and Kenya,” I wrote, “stories that need to be told.”

For a moment, I wondered if I should run this line by a foreign-policy expert. That’s what Litt would have done. But then I thought better of it. Lips didn’t need some egghead to tell him how to craft a sentence. You lump the countries ending in yuh sounds together. Everything flows perfectly. The crowd goes wild. The end.

On Saturday night, my confidence was rewarded. Dressed in a tailcoat, wing-collared shirt and white bow tie, I descended the escalator to a ballroom in the Renaissance Hotel. Just feet from the stage, I watched costumed reporters sing “My Gun” to the tune of “My Girl.” Louisiana Governor Bobby Jindal and Minnesota Senator Amy Klobuchar delivered monologues in front of a giant, glowing spatula I can only assume was the club’s namesake Gridiron.

Then, just before “Auld Lang Syne,” POTUS spoke. The laughter was consistent and chummy. The jokes singed, but never burned. During his serious close, President Obama praised reporters for risking everything in places like Syria and Kenya. Everything flowed perfectly. The crowd went wild. Lips was fucking crushing it.

On Monday, back in the office, I was a paragon of false humility. Other speechwriters told me the remarks had been great, and I replied that it was all in the delivery. At 26 years old, I dispensed wisdom to the staffers fresh out of college. “When you think about it,” I intoned, “Credit belongs to our entire team.”

I was on top of the world, wondering if I might actually be the best wordsmith in history, when I heard from one of the president’s longest-serving speechwriters, a soft-spoken Massachusetts native named Terry. He wanted to know if I’d seen an article in the Daily Nation, a newspaper published in Nairobi.

KENYA NOT SAFE FOR FOREIGN JOURNALISTS, SAYS OBAMA

It took some frantic googling, but I pieced together what had happened. The White House press office had released the full transcript of POTUS’s Gridiron speech. When Kenyan officials read it, they noticed their country featured in the same sentence as one of the world’s most despised regimes.

They were not happy at all.

Bitange Ndemo, Kenya’s permanent secretary for information and communications, released an official statement calling the president’s words “not only inaccurate, but exceedingly disturbing.” A group called KOT (Kenyans on Twitter) created a brand-new hashtag to channel their rage.

If you’ve never angered a country of more than 45 million people before, it might seem like a power trip. It’s not. Sitting in my office, typing Kenya angry at Obama into the search bar over and over, I felt more helpless than ever. What I wanted more than anything was someone I could talk to—a Kenyan I could call. “You think your entire country is mad at my entire country,” I would explain, chuckling at the mix-up, “when really it’s just little ol’ me.”

But no such Kenyan existed.

Instead, senior staff were forced to busy themselves playing cleanup. These were people with serious responsibilities, global priorities on their plate. Now they had to take time away from far more worthy objectives to deal with my mess. Even then, it took an official apology on America’s behalf to put the controversy behind us. “We recognize and commend the press freedoms enshrined in Kenya’s constitution,” said an unnamed White House official. “Obviously, the situations in Syria and Kenya are quite different.”

Perhaps Lips was not crushing it after all.



***

I spent the rest of the day wondering if antagonizing a mid-size African nation was considered a fireable offense. But in the White House, I learned, it’s not so cut-and-dried. I wasn’t the first young staffer to find their smallest screw-up magnified to national scale. I wasn’t even the first speechwriter to piss off another country by mistake.

In the weeks that followed I continued trying to put myself back in my team’s good graces. It didn’t go well. My big chance, a draft of a speech about infrastructure finance, got “blown up,” a word that described both the condition of the speech and the ego of the speechwriter responsible. Watching the president deliver the remarks Cody had rewritten, I was struck by just how much better they were than my original attempt. In the two years since I’d first been hired by the White House, I had never felt so utterly like a fraud.

It wasn’t supposed to be this way. The 2013 Correspondents’ Dinner was approaching. I was more responsible than ever for the speech. But instead of relishing my new role, I was living the exact opposite of a superhero’s life. By day, I was a mild-mannered speechwriter. By night, I was a mess.

Joke writing—as opposed to most White House speechwriting—was a group effort. For three weeks, about a dozen people sent in submissions. Former wordsmiths (and future Pod Save America hosts) Favs and Jon Lovett pitched jokes from Los Angeles. From Chicago, David Axelrod sent in submissions and initiated long email chains full of puns. A handful of professional comedians offered their services pro bono as well.

Knowing that so many people were hard at work took a little bit of the pressure off, but not much. When people asked me what my role was with the Dinner, I told them that if things went poorly, it would be my fault—and I had no desire to find out if I was right.

But it was too late to back down. I curated the jokes that came in from around the country. I contributed my own. With about a week before the dinner, we had cut our additional list of hundreds down to about forty, and it was time to present them to POTUS. Once again, Cody strolled confidently into the Oval. Once again, I tiptoed behind.

The joke that most worried me involved the political landscape post-campaign. (This was during the brief period when the GOP hoped to expand beyond its base.) “One thing Republicans can all agree on after 2012 is that they need to do a better job reaching out to minorities,” the script read. “Call me self-centered, but I can think of one minority they could start with.”

It was the kind of line we never would have written in the first term. No one could remember POTUS referring to himself as a “minority” before. But with the reelect behind him, President Obama was eager to push the envelope.

“That’s pretty good,” he chuckled. He even promised a personal touch. “I might add a little wave there. Maybe a ‘hello,’ or something.” How strange. There I was, sick with nervousness, and POTUS was having fun.

The rest of the meeting passed without incident. President Obama approved some jokes, told us to make others edgier and sent us on our way. But surviving 10 minutes in the Oval couldn’t erase my feelings of fraudulence. The days of proudly strutting back to my office were over. The days of dark, harrowed circles under my eyes had begun.

POTUS often challenged us to write material that was “sharper” and “edgier,” and 2013 was no exception. A few days before the dinner, a second meeting gave him a chance to review our latest attempt. (“A book burning with Michele Bachmann. I like that!”)

It also gave us the opportunity to show him slides. Not everyone approved of displaying silly, photoshopped pictures in the middle of the president’s monologue. Compared to well-delivered setups and punch lines it felt like cheating, and to some extent it was. But if years of writing have taught me anything, it’s that people hate words and love pictures. Why not give them at least some of what they want?

Besides, POTUS liked the slides almost as much as the audience did. He laughed when he saw his face on a cover of Senior Living Magazine. He appreciated our putting a “Blame Bush Library” next to the real thing.

Most of all, he enjoyed a series of three pictures photoshopping the first lady’s new hairdo—eyebrow-length bangs—onto his head. POTUS with bangs, in front of an American flag. POTUS with bangs, relaxing alongside his wife. POTUS with bangs, walking side by side with Israeli Prime Minister Bibi Netanyahu. In the edited images, President Obama looked like Moe from the Three Stooges. It was hard not to laugh.

In fact, there was only one slide the president felt the need to change. A few weeks earlier, the White House had released a photograph of the president shooting clay pigeons at Camp David, and his critics accused him of doctoring the image. Obama, they insisted, was a gun grabber. His only reason for holding a firearm would be to melt it into a solar panel, or stuff the barrel with a gay pride flag. Their accusation was ludicrous, of course, utterly bananas. Naturally, it spread like wildfire on right-wing blogs.

Now, at Cody’s suggestion, we were going to present an “undoctored” image to the world. In our picture of what had “really” happened, POTUS was still firing a gun. But in the background, we added a lightning storm, a monster truck and a kitten the size of a black bear shooting lasers from its eyes. As we prepared to leave the Oval, POTUS held us back. He had an edit to request.

“Can we get a NASCAR in there?”

“We can do that,” I said.

President Obama smiled contentedly. Then he perked up, struck by a sudden insight.

“Can Biden be driving the NASCAR?”

By now, even I had to admit that I seemed not to be screwing up too badly. By Friday afternoon, just 24 hours before the dinner, I even began to consider the possibility that everything would go as planned.

And then, sitting in my office, I got a phone call. It was Terry. He had a question.

“So I’m looking through these pictures of the president with the First Lady’s bangs, and I’m just wondering. Is the joke supposed to be that POTUS looks like Hitler?”

I immediately opened the slides in question. The first photo was harmless. So was the second. Then I reached the third slide, the one with the president and the Israeli prime minister.

“Oh,” I said.

“Yeah,” he said.

It was shocking. These were the olden days when the president’s opinion of Nazis, neo or otherwise, was not in question, and I stared in horror at the image on the screen. The president didn’t ordinarily look like Hitler in photographs. He certainly didn’t look Hitler-y in person. But at that exact angle, with that specific haircut, there was no mistaking it. Even without the mustache, the resemblance was uncanny.

Just a month earlier, I might have tried to keep the slide in the script anyway. It was funny. Besides, would anyone think we were trying to make POTUS look Hitler in a slide? But I wasn’t risking another international incident. I was done listening to Lips. Thanking Terry profusely, I hurried to save my speech.

On April 27, the day of the dinner, Cody was at a wedding. But Favs and Lovett were in town for the occasion, and they joined our day-of meeting instead.

These final run-throughs were always casual. Instead of sitting at his desk or in his armchair, the president plopped down on a couch. As usual, the meeting began with small talk. POTUS asked Favs about his new speechwriting business. He teased Lovett about his life in L.A. Meanwhile, I sat there stunned. I couldn’t believe how casually my former colleagues charmed the president. What better proof that hiring me at the White House was a mistake?

I was so busy wallowing that I barely heard POTUS ask a question.

“What happened to that picture of me and Bibi? I liked that one.”

Favs jumped in. “We had to cut it.”

“Well, why?”

New Window Excerpted from Thanks, Obama: My Hopey, Changey White House Years. (Click to buy the book.)

Suddenly, the Oval Office fell completely silent. Plenty of people have compared the president to Hitler. But in all of American history, no one had ever compared the president to Hitler to the president. And none of us wanted to become the first.

It turns out that time slows down when you’re trying not to insult the commander in chief. I remember considering, in surprising detail, just how doomed we were. Favs wasn’t saying anything. Lovett wasn’t saying anything. I wasn’t saying anything. There was no way out.

There must be someone in this room who can tell the president the truth, I thought. But I couldn’t begin to imagine who it might be. We needed someone bold. We needed someone daring.

We needed someone who didn’t give a fuck.

In that moment, out of nowhere, I heard a voice. And it was Lips.

“I’m sorry, Mr. President,” I heard myself say, “we just couldn’t use that picture. You kind of look like Hitler in it.”

The moment the words left my mouth, my out-of-body experience ended. What had I just done? All eyes were on POTUS. Nothing like this had ever happened before.

And then, President Obama began to laugh. Not his ordinary laugh, a self-aware one that was an act of thoughtful consideration as much as reflex. This was an expression of something visceral inside him, a place beyond even his formidable self-control. He clasped his hands together. His feet kicked off the floor. He rocked back into the couch cushions. For just a fraction of a moment, I even think he forgot which person was the president. I had never seen him laugh so hard, and would never see him laugh so hard again.

Eventually the meeting returned to normal. Favs and Lovett resumed their confident banter, and I went back to sitting quietly on the couch. But I realized something. For the first time, I wasn’t afraid.

The president finished his read-through not long after. We stood to leave, clutching our copies of the script. Before I could reach the door, however, POTUS looked right at me.

“Thanks, Litt,” he said.

From Thanks, Obama by David Litt. Copyright 2017 David Litt. Excerpted by permission of Ecco, an imprint of HarperCollins Publishers.