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  Also, the ratio between reward and risk was perilously skewed. If I did my job flawlessly, no one would notice. Fail to properly attribute a quote, however, or omit the L from public investment, and my mistake would be national news. Each day brought a once-in-a-lifetime experience, but each night brought intensely literal dreams about work. Tomorrow’s speech left a senator unthanked. I had botched the phonetic spelling of buenas noches. I had failed to confirm a statistic with the relevant policy team.

  The focal point—of both my workdays and my nightmares—was a black plastic rectangle the size of a deck of cards: my BlackBerry. By 2011, the BlackBerry was already becoming an anachronism. It was as if the entire federal government had signed up for Jazzercise, or gone to Blockbuster to rent Space Jam on VHS. It didn’t matter. Like nearly every White House staffer, I lived and died by my device. Before long, I developed a Spidey-sense for incoming e-mail. My nerves would tingle, I would check the home screen, and then, a millisecond later, the red light on the top right corner would flash.

  At the time, I didn’t see this as a warning sign. It was a badge of honor. The moment a new message appeared, my thumbs leapt into action. I could read a chain of messages, reply to the sender, and relock the screen within seconds, all while carrying on a separate conversation face-to-face. I was an e-mail samurai.

  I was also, however, a basket case. I would never have admitted it, but each new message triggered a fight-or-flight response. Every blinking light meant Valerie had another round of edits, or that a new set of talking points had to be composed ASAP. The only thing more frightening than a flurry of new e-mails was no e-mails at all. Just three minutes without feeling a vibration in my holster, and full-blown panic would set in.

  Is there a malfunction? Did I miss a reply? Should I ping someone to ask why no one’s pinging me?

  I told myself I was handling the pressure. Then one afternoon, several hundred e-mails into my day, I yawned and something popped. Almost immediately, my right cheek ballooned. My face pulsed and throbbed. A few seconds of googling gave me a diagnosis: temporomandibular joint disorder. In layman’s terms, I had clenched my jaw so tightly it had simply given way. Far more shocking than the injury, however, were my coworkers’ reactions. When I described my condition to Jessica, a liaison in intergovernmental affairs, I assumed I’d get some sympathy. Maybe she’d even advise me to take the day off.

  “Yeah, that happens a lot,” she said, barely looking up from her computer. “First time for me was on the John Edwards campaign. Just don’t chew for a while.”

  I followed her advice, and a week later my jaw no longer ached. But as my BlackBerry kept up its incessant buzz, I couldn’t help but wonder if the White House had made a mistake. I had at least some talent. I was sure of that. Yet I also knew that there were more than three hundred million people in America. True, some of them were babies. But a lot of them were adults. It seemed unlikely that I was the best We, the People, could do.

  ON THE LAST WEDNESDAY MORNING IN APRIL, I WALKED BY STRAUT’S office and noticed a crowd gathered around his TV. This was unusual. At the White House, televisions were almost always muted, the manic gestures of cable-news pundits a silent backdrop for actual work. Now, though, the volume was turned up full blast. In the center of the screen was President Obama, making an announcement from the briefing room. He looked profoundly annoyed. I turned to Alex, Straut’s assistant.

  “Holy crap! He’s releasing his birth certificate?”

  My introduction to the birther movement had come a few years earlier, through a blog written under the pen name “Texas Darlin.” Texas was one of the few Hillary supporters who hadn’t come around. Instead, it was as if Catholics and Protestants had split, and she’d responded by turning to Satan. Her posts made even Sarah Palin look restrained.

  I kept tabs on Ms. Darlin’s blog the way a coal miner keeps tabs on a canary. If she floated a conspiracy theory on Easter, by Christmas it would be part of the conservative mainstream. Still, when she began warning readers that Obama was born in Kenya, I was certain she had gone too far. Who could possibly believe that? I thought. And then, just a few months later, millions did.

  If people like Texas Darlin kindled the birtherism epidemic, it was real estate mogul Donald Trump who fanned the flames. It seems unbelievable now, but in 2011, Trump’s star was waning. His reality show was losing its audience. America was tiring of his brand.

  Then, in a reboot of epic proportions, Trump began demanding the president’s birth certificate. It was impossible to tell whether his act of showmanship was a triumph of strategy or instinct. Either way, it came with an adoring, built-in audience. A sizable chunk of red-state America was desperate for a hero, someone to unmask the foreignness of the president they loathed. Within weeks, Trump was leading a kind of anti-Obama revival movement. Instead of covering the administration’s agenda, reporters began covering the birthers’ antics. No wonder the president looked pissed.

  And now he had called the Donald’s bluff, posting his long-form birth certificate on the Internet for the entire world to see. Those of us standing around Straut’s television unanimously agreed this was badass. In a single stroke, President Obama had just delivered a fatal blow to birtherism. He had exposed its most famous cheerleader as a fraud.

  Best of all, he had done it just three days before he would see Donald Trump in person. That Saturday, they were both scheduled to attend the White House Correspondents’ Dinner.

  BECAUSE THE CORRESPONDENTS’ DINNER PLAYED AN OUTSIZE ROLE in my White House career, I should acknowledge up front that it is bonkers. Imagine learning that once a year the British prime minister leads a mariachi band, or the Chinese premier performs burlesque. Yet in America, tradition dictates that each spring our commander in chief don black-tie attire and perform a comedy monologue in the ballroom of a Washington hotel.

  In some ways, it’s a fairly modern ritual. While every president since Calvin Coolidge has attended the dinner, most didn’t tell jokes. Those who did kept their remarks focused on the relationship between the chief executive and the press.

  Then, near the end of the Reagan era, reporters began inviting celebrities. Celebrities began showing up. In 1997, red-carpet buzz reached new heights when Ellen DeGeneres and her then-girlfriend Anne Heche arrived. In 2002, Ozzy and Sharon Osbourne accepted invitations at the peak of their reality-show fame. By the time President Obama took office, what was ostensibly a fund-raiser to provide scholarships for high school students had become a bilateral summit between Hollywood and Washington, D.C. The night was nicknamed Nerd Prom, but Name Dropper’s Paradise would have been just as accurate.

  “As I overheard Chris Christie tell Sofía Vergara . . .”

  “That reminds me of a joke I told the Secretary of Labor, Kim Kardashian, and two-thirds of the cast of Glee.”

  Each White House handles amateur night differently. Bill Clinton’s staff fought tooth and nail to land their favorite lines, backstabbing colleagues without remorse. I once asked a Clintonite how to gracefully cut subpar jokes, and he told me not to bother. “If a joke really stinks,” he advised, “push it into the middle of the highway. Let it get run over by a truck.”

  George W. Bush’s team was less cutthroat, but also less confident in their principal’s ability to perform. They often let goofy slides do the heavy lifting, while the president read captions that were difficult to screw up.

  Obama’s process was defined not by infighting or caution, but by an ironclad if unwritten rule. Everyone stayed in their lane. Jon Lovett was the president’s funniest speechwriter—his color commentary was a fixture of our team meetings—so he was in charge of the jokes. Favs made edits and shaped the flow of the script. David Axelrod, already in Chicago for the reelection campaign, served as a kind of professor emeritus, offering advice, pitching one-liners, and initiating long e-mail chains full of puns.

  Another dozen or so writers—some from the comedy world, others from politics—sent in jokes as be
hind-the-scenes volunteers. It was in this role that I had landed a few lines in the previous year’s script. Now, however, I was on the inside. I was sure I had more to contribute. I hoped I would finally get my chance.

  In many ways, I did. Favs and Lovett found me a ticket to the dinner. When we had to tweak setups or edit transitions, they welcomed my two cents. Also, because I could see each draft of the monologue, I knew in advance which lines would make the cut. As the day of the dinner neared, I had four jokes in the speech—not an overwhelming number, but respectable. I was especially proud of a line I’d written about one of the 2012 Republican candidates, in response to the birther mess.

  “You may think Tim Pawlenty’s all-American, but have you heard his full name? That’s right: Tim ‘bin Laden’ Pawlenty.”

  I could picture the shock rippling across the audience, followed by a wave of laughter. It was going to be epic. I couldn’t wait.

  Still, the dinner wasn’t the big break I was hoping for. Access to drafts aside, I found myself excluded from the joke-writing inner circle. I understood why Favs and Lovett didn’t rush to include me in their Oval Office meetings. They didn’t yet know if I could be trusted with information reporters would cut off a pinkie to obtain. But it stung to be so close and yet so far.

  The day of the dinner, as I scoured Washington in a desperate search for cuff links, Favs, Lovett, and Axelrod met with the president in the Oval one last time. Not long after, the red light on my BlackBerry flashed. An updated draft. Some of the changes were hilarious, especially the long run of jokes that Lovett and Judd Apatow (one of our comedy-world silent partners) had written torching Trump. But as I scrolled through the latest version, I was stunned. They had butchered my best line. The reference to bin Laden had been deleted. In its place was the name of the Egyptian strong man deposed a few months before.

  “You may think Tim Pawlenty’s all-American, but have you heard his full name? That’s right: Tim ‘Hosni’ Pawlenty.”

  Something inside me snapped. Yes, I was an entry-level speechwriter. Yes, everyone pays their dues. But this was absurd. How could they possibly think Hosni was funny? Were they too scared to have the president say the name of the world’s most wanted terrorist? Did they not realize that was the entire point? And besides, think of the phonetics. Say what you will about the man, but bin Laden has a ring to it. You’ve got the rhyming syllables on both sides, with a hard consonant in between them. Hosni is garbage. It starts out all flabby. It has no discernible end. Anyone could see that.

  Even worse, when I complained to Favs, he told me the edit had come from the president himself. Well, tell him to change it! I thought. Aren’t you supposed to be the speechwriter? For the first time since walking through the gates, I was 100 percent sure the White House needed my opinion. I whipped out my BlackBerry. Thumbs flying, I furiously typed a manifesto. I called up the menu of options. I placed my finger on the SEND button.

  Then, abruptly, I paused. It was as if a tiny bureaucratic angel was whispering in my ear.

  Stay in your lane. Staaaaay in your laaaaane.

  Slowly, I holstered my BlackBerry. I went home and put on my tux. Then, ticket in hand, I took the bus to the Washington Hilton.

  That night, I gawked at enough famous people to last a lifetime. I watched Amy Poehler search for her table. I witnessed Bradley Cooper mingle before taking a seat. I stared at Treasury Secretary Tim Geithner as he chose between finger foods at the reception. And from the back of the room, I watched President Obama’s monologue, the best he had ever delivered. During the section on Trump, hundreds of Democrats and Republicans joined in bipartisan, mocking laughter. As the crowd applauded the president, the humiliated billionaire turned as red and angry as a blister.

  Well, I remember thinking, that’s the end of this guy.

  The only downside of the night was Hosni. My joke fell flat, just as I had feared. I couldn’t understand why no one else saw it coming. As the program ended, important people filed out of the ballroom to attend exclusive parties. I returned home to tell my friends about the time I used the urinal between Newt Gingrich and Jon Hamm. Still, for all the glamour, the night left me unsettled. I had been right about that punch line. I could have fixed it. Why didn’t anyone listen?

  The next morning, in a minor act of protest, I did something unthinkable. I turned my BlackBerry from vibrate to silent. Then I went to a music festival in Maryland with two friends from college, Nick and Claire. I wore a T-shirt and flip-flops instead of a suit. I drank a beer during daylight hours, even though Valerie had a speech tomorrow and I might be called upon to edit at any moment. For the first time since Straut told me I was hired, I felt twenty-four again.

  All too soon, our day of freedom ended. I wasn’t exactly thrilled about returning home. Glowering reluctantly in the back seat of the car, I switched my BlackBerry from silent to vibrate and it buzzed almost immediately. More talking points from Straut, I figured, or maybe a last-minute change to tomorrow’s speech.

  It was neither. To my surprise, the sender was Ben Rhodes, the president’s chief foreign-policy writer. The subject line included the word FINAL and the acronym UBL. I was confused. POTUS wasn’t scheduled to deliver a speech that evening. Also, I had no idea what those three letters stood for. Unresolved Banking Liability? Unanimous Bipartisan Legislation? Puzzled, I opened the e-mail.

  Remarks of President Barack Obama

  On the Death of Usama bin Laden

  The White House

  May 1, 2011

  I was suddenly very glad I hadn’t hit SEND the night before.

  The news broke on Twitter a few minutes later. Nick, Claire, and I drove toward Washington, collectively freaking out. When we reached D.C. we tried watching CNN at a bar, but something felt off. Like moths responding to a stadium light, we each had the same instinct at once.

  “Let’s go to the White House!”

  By the time we got downtown, Pennsylvania Avenue was packed with young Americans. College students waved flags and raised their arms in triumph. Bros hoisted fellow bros on their shoulders. Out of nowhere, people began singing the national anthem. Then they switched to an old chant, one I always associated with the Yankees winning a game.

  Nah-nah-nah-nah, nah-nah-nah-nah, hey hey-ey, goood-bye.

  I had never been part of such a raucous celebration, not even on Election Night. But looking from face to face, I didn’t see joy or triumph. I saw relief. For people my age, 9/11 was the formative experience of our formative years. As kids, we were told America could do anything. Then a terrorist attacked our country and murdered thousands of our people, and we couldn’t catch him no matter how hard we tried. For a decade, that failure cast a shadow on the promise we were raised to believe. Now, the shadow had been lifted. America had done what America set out to do.

  Hey hey-ey, good-bye.

  My BlackBerry vibrated. It was Valerie, with major changes to tomorrow’s speech. She wanted to talk about the president’s courage. She wanted to speak to his judgment, to his character, to the way those qualities had been present when she met him two decades before.

  I hadn’t ordered any raids. I hadn’t been in the Situation Room, or even near it. But early the next morning, long after the crowds had left Pennsylvania Avenue, I would return. I would walk through the gates of the White House and do something, however small, that needed doing. In all likelihood, I was still not the best my country had to offer—my former TA could vouch for that. But in that moment, the question of whether I belonged seemed less important than the fact that I was here. In some small way, America was counting on me. In some small way, I was part of the team.

  Still, though. Hosni? They really should have gone with Saddam.

  4

  THE CORRIDORS OF POWER

  ALEX (early twenties, staff assistant): Can you help me with this e-mail?

  DAVID (early twenties, speechwriter): Sure, what do you need?

  ALEX: We’re replying to a CEO. I don’t want him t
o think we’re blowing him off.

  DAVID: Okay, but what are we doing?

  ALEX: We’re blowing him off.

  In my five years at the White House, this was the first and only time my life resembled the television show The West Wing. That was not for lack of interest. Like nearly every Democrat under the age of thirty-five, I was raised, in part, by Aaron Sorkin. During my freshman year of college, my friends and I watched West Wing DVDs on an endless loop, pausing only when our born-again roommate held pop-up Bible study in our suite.

  MARK (deeply earnest): Have you ever wanted to learn more about Jesus?

  DAVID (equally earnest): Have you ever seen the last episode of season two?

  The witty banter. The brilliant grouches barging into the Oval Office. The satisfying conclusion each week. We couldn’t get enough. But being introduced to politics by The West Wing was like being introduced to sex by Debbie Does Dallas. No matter how much more satisfying the real thing was than fantasy, in certain ways it was bound to come up short.

  This was especially true when it came to office space. On the DVDs I devoured, the West Wing was spacious and grand. In real life the West Wing is a human ant farm that received its last major renovation in 1934. To be fair, the Oval Office looks like it does on television. A few of the president’s top advisors occupy large, wood-paneled rooms best described as “robber-baron chic.” But dozens of remaining staffers are squeezed into tiny outer offices, or piled clumsily on top of each other like dirty dishes in a sink.

  The result was the world’s most Type A sweatshop. At a time when Silicon Valley lured talent with ball pits and Ping-Pong tables, some of the most coveted jobs in Washington offered less personal space than Walmart during a Black Friday sale. Signs of overpopulation were everywhere. During peak hours, the line at the Navy Mess takeout window was so long you wondered if there might be a roller coaster at the end of it. In the ground floor that doubled as a waiting room, a faint odor of sewage occasionally infused the halls.