West Winging It

by Pat Cunnane

  The list was made up of ideas, some quite “out there” and probably a bridge too far, that remained presidential possibilities. I added one titled “Bike to Work Day”: I suggested that POTUS grab his bicycle and ride down Pennsylvania Avenue to the Capitol on National Bike to Work Day to deliver a speech about the work that Congress needed to do. That one landed flat, as did a bit that many staffers suggested about sending Obama to a classroom as a substitute teacher, blackboard and all, to embrace his tendency to slip into “professor mode.”

  Velz and I worked very hard to get Howard Stern into the mix. We wrote a detailed memo to our bosses outlining the many pros to a sit-down with the “King of All Media,” an unusually thoughtful interviewer with a vast audience that we would do well to connect with. Now, the reason we weren’t risking our jobs submitting a memo that called for the commander in chief to get chummy with a formerly infamous shock jock dates back to 2014.

  It’s the same reason a lazy drive for coffee wasn’t a nonstarter and why it seemed to “have merit.” For opening up these new avenues, we owed a debt of thanks to an irreverent, derisive man named Zach Galifianakis. The playing field that presidents use to engage the public was changed in March 2014 when Obama famously appeared on the rumpled comic’s Between Two Ferns—a popular web series that thrived on discomfiture—to promote the Affordable Care Act.

  Part of the conceit of the show is that it’s amateur hour, which would contrast perfectly with the professionalism of the White House. So, in late February 2014, the crew brought dinky Ikea end tables, which Velz helped to set up before the shoot. Following the taping, he approached Upper Press with the famous ferns in hand. After giving one to Schultz to help spruce up his sparse office, Velz recounted the interview through fits of laughter. We were all a bit nervous, given that this was a unique format that involved line reading and acting, as well as improvisation on the part of the president.

  The tone was set early when the audio guy haphazardly miked POTUS at the door to the Dip Room. He applied a large piece of white tape to the outside of the president’s navy lapel and let the cord hang loose. Amateur hour. On purpose.

  The point of the show is that Zach is super annoying. And POTUS was to play the annoyed, mildly offended counterpart. Problem is, the room couldn’t tell on first run-through whether the president was just a solid actor or genuinely pissed off. After all, Zach did ask what it felt like to be the last black president and called POTUS a “nerd.” Velz and Valerie Jarrett, as well as Jay and Cody, held their breath. Then a wide grin gave it away.

  POTUS was in on the gag. And he crushed his performance. Velz said he and the other staffers standing off to the side of the Dip Room could barely hold it together—that it was nearly impossible not to burst out laughing. Velz, who spent a good deal of his days opining with unusual sophistication on the latest television shows and movies, was spot-on in his review. He predicted it would be a hit, and America agreed with him.

  The results were remarkable. We reached the young audience that we needed to sign up for health care through the as-of-then much-maligned website HealthCare.gov, which had a very bumpy rollout. Enrollment for the president’s signature legislative achievement was lagging behind expectations. We needed a jolt. Six minutes on a campy video series provided just that. Visits to HealthCare.gov skyrocketed 40 percent, enrollment was up, and the fake interview has been viewed more than fifty million times. It got us back on track—well, at least until one month later, when the White House red fox story pushed it off the evening news.

  We knew we had something. We’d proven the concept.

  The second term allowed us to take more chances than the first. We didn’t mind if the Right ripped us for the Galifianakis interview, which they did. (Bill O’Reilly helpfully reminded his viewers that Lincoln wouldn’t have done it.) The truth is, right from the start of the administration, the president pushed the envelope. It seems commonplace now, but he became the first sitting president to do a late-night interview (with Jay Leno for The Tonight Show), adeptly mixing moments of comedy with policies of consequence.

  Around the same time of the Between Two Ferns interview, we pulled out all the stops, pressing the issue of ACA enrollment. It was a stretch of time, under the determined leadership of Denis McDonough, fully focused on salvaging Obamacare—of transforming the term from punch line to triumph.

  I remember writing a memo to the president the night of February 6, 2014: “You will take part in an interview with Mista Madd for the Madd Hatta Morning Show.” There was a space at the top of each memo labeled “From.” I was so embarrassed to be explaining Mista Madd’s clout in the Houston urban and rap establishment that I tried to keep my name off it. I thought back to one of my bosses relating a story from the last time Obama had given such an interview. “Oh, the indignities of this office,” he’d said with a sigh from the Resolute desk.

  This was sure to be another indignity, I thought. Still, it wasn’t up to me. We needed to promote enrollment, so I continued with the memo—putting in the usual talking points, tough questions and answers, and relevant statistics. And the next day, as we got a call from the Outer Oval that he was ready, I quickly printed a copy for Jennifer Palmieri and handed it off, fingers crossed.

  A few minutes later, she was back, her face red with what I hoped was laughter and not anger.

  “JPalm . . .” I said tentatively.

  Turns out after she told the president that he should address the Madd Hatta as “Mista Madd,” the president flipped to one of the last pages of the memo, pointed, and said, “Here’s what Mista Madd is not going to ask me about: the CBO report.” Jennifer and another staffer, Tara, burst into laughter, which Pete Souza caught at just the right moment. It could be hard to know what to include in the president’s memos—what mattered and what didn’t. He was probably right in this instance, but there were times when things left out of the memo came back to bite us.

  My colleague Jeff and I had been pushing our bosses for months to send Obama to Chipotle. We both loved the place, and at the time, America did too. Finally, they relented, sent Obama on an OTR to Chipotle. Couple things: like so many middle-aged men and women, he needlessly added the possessive—Chipotle’s—which is a particular pet peeve of mine. I’ve found that the most common version of this invented possessive is Nordstrom’s.I It’s almost impossible for me not to correct that one. My dad gets particularly frustrated when I correct him on his invented possessives, but then I remind him that he once thought human babies don’t open their eyes for months.

  Still, most didn’t notice the president’s minor gaffe, because he made a major gaffe the same day. You see, I didn’t think it necessary to include in the memo that one does not reach one’s arms over the sneeze guard to point to what one would like to order. Turns out, I should have. Obama was captured on camera hulking over the protective glass. As New York magazine put it: “Obama Leans over Chipotle Sneeze Guard, Infuriates Nation.” It was his Swiss-cheese-on-a-cheesesteak moment, John Kerry’s famous faux pas at Pat’s King of Steaks in Philly.II This was a few months after Mista Madd, and I had learned my lesson—that regardless of what the president thinks, best to include. Better safe than out of touch at “Chipotle’s.”

  For a long time, Souza’s jumbo of JPalm hung in Upper Press, a constant reminder that we’d once put the president on the phone with Mista Madd. And, more importantly, that the world didn’t end. Maybe it was “unpresidential,” but if it got an additional person to sign up for health insurance, it was worth it.

  We were as comfortable as we were with any of this, because Obama had proven from his first correspondents’ dinner performance that he could deliver a joke. In fact, that’s the only reason Jerry was interested to begin with. He wouldn’t invite just any president onto his “little show,” as he described it. According to the comedian, Obama had landed just enough one-liners to qualify.

  • • •

  I’ve talked about how he could be self-deprecati
ng, but Obama saved many of his best barbs for others. It was hard to predict how the president’s foils—from Trump in 2011 to journalists in 2016—would respond, but Jen Psaki knew when she saw the first draft of the 2016 speech that one of the targeted reporters would be offended. Even though the joke was lighthearted, she pushed for its removal but was eventually outvoted.

  I assumed that any reporter who was mocked by the president from the podium would take it as a badge of honor: a sign of grudging respect; that you’d risen to such heights that the president would care to knock you down a peg by poking fun.

  I assumed wrong. Jen was right, and for her foresight, she was rewarded with upset emails from the butt of the president’s punch line. The reporter had taken the hit to heart, assuming there was some sort of personal animus behind the barb.

  The shot got a good laugh in the room. Probably not worth the headache it caused Jen, but a solid laugh nonetheless. I was crowded into a table in the corner of the massive ballroom. Hadn’t heard back from Tyler, the speechwriter in charge of the last speech, on whether any of my jokes made the final cut, so I knew to assume that none did. That is, until I heard the president start down a familiar setup and then land my punch line! I almost fell out of my chair. I was overjoyed. And then a few minutes later, it happened again. I was stunned.

  Tyler came up to me at one of the after-parties—he was genuinely excited. “I wanted it to be a surprise!” he said. “You got two in—same as Larry David.”

  And with that sentence, I felt my time at the White House had reached its peak. Obama ended his speech by raising his microphone and bellowing “Obama, out!” As he dropped the mike to the floor, and the crowd rose, I couldn’t help thinking about how well it was all working out. Sure, I was sad things were ending, but he was going out on a high, Hillary was just a few months from election, and I had gotten jokes into what was “perhaps the last” White House Correspondents’ Dinner.III

  Months later, in the immediate lead-up to the election, we were preparing for a visit to Jimmy Kimmel’s late-night show. We received what I thought was a genius idea. Jimmy’s team had asked to have the president perform iconic speeches from famous presidential TV shows and movies. Independence Day, for instance, when Bill Pullman delivers a soaring call to action in the face of an alien invasion. Or the one we suggested back to them, when Michael Douglas’s President Shepherd beats back his rival in a stirring defense of his girlfriend at the climax of The American President: “This is a time for serious people, Bob, and your fifteen minutes are up. My name is Andrew Shepherd, and I am the president.”

  But when the president received our memo, though he thought it funny, he decided no. We went with a proven winner, another segment of “Mean Tweets,” in which the president read mean tweets about himself. Helping to cull through the real mean tweets in contention for reading on the air was a trip. We navigated them well, I thought, choosing the correct mix of random, mean, and funny. Turns out, we screwed up the last one.

  For the big finale, he read a tweet from @realDonaldTrump: “President Obama will go down as perhaps the worst president in the history of the United States!” Then Obama looked at the camera and said, “Well, @-real-Donald-Trump, at least I will go down as a president.” Then he dropped the phone.

  • • •

  It was always about more than being funny. We made a concerted effort to meet Americans where they were—and where they were was changing. Nobody understood that better than Jason Goldman. He, more than most, recognized that “during the Obama presidency, there was this dramatic shift in how people consumed information.” As he put it to me recently, “People forget that in 2008, we were on the second iPhone, that the mobile revolution hadn’t fully happened, that while Facebook existed, mobile video didn’t. And while Twitter existed, it was in its infancy.”

  So as these now-ubiquitous mediums matured, our strategy for communicating with the world needed to grow up too. We were a bunch of Millennials trying to keep up. That’s not to say that Comedians in Cars Getting Coffee would replace Meet the Press or that YouTube video gags would replace conventional press briefings. In fact, throughout our second term, traditional journalistic outlets continued to represent the most meaningful channel to communicate the president’s message. But we would have been negligent not to adapt. “We had to embrace a strategy where you didn’t try to reach everyone at once but instead were very specific about who you were trying to reach and why,” Jason said.

  Yet social platforms have their benefits and their drawbacks. They allowed us to connect in a deep and meaningful way with a niche—granted, sometimes still very large—audience. But as Jason cautioned, it can be a difficult platform for persuasion: often we were connecting with folks predisposed to agree with what we were selling. And we were wary about devolving into an echo chamber. We already saw that beginning to take root on the Right, and Jason was well aware of the “robust marketplace for dark conspiracy on the web.”

  That’s why it was so important to me that the Seinfeld conversation be content free. An interview about nothing. I wanted it to exist in a sort of media vacuum—even as, all around us, things were changing.

  During some downtime in the office, I read an article in Wired about a crazy-looking bird called the crossbill, named for its peculiar bill, which crosses awkwardly over itself. It evolved that way to do battle with a type of pine tree that’s developed sturdier cones specifically to try to keep the crossbill out. They’re locked in what’s called coevolution: two distinct species evolving in response to each other. It reminds me a great deal of the mutuality between the president and the press that I described in chapter 3, and it informs what my position toward the end of the administration was all about.

  By the time I became deputy director of messaging, the coevolution (or devolution) of the press corps and the White House communications strategy was well under way. Things had changed in just a few years. Think about it: at the beginning of 2015, President Obama’s voice didn’t exist on Twitter. “Despite having tens of millions of followers,” Jason recently told me, “the @barackobama account was considered a campaign asset, and most of the content there was not in his voice; only those signed ‘-bo’ were from him.” So in 2015 the White House created @potus, and, Jason said, “The president directed that all of the content on that channel would be in his voice, and he would be involved personally in the creation of it.”

  Of course, the creation of his official account didn’t mean POTUS was up early tweeting out his frustrations with the media or musing online late at night in the residence about policy. For the most part, according to Jason, “Our stance with @potus was not to use the channel to break news, because we both felt an obligation to the traditional media covering the White House and felt that policy announcements—in particular—were more appropriately rolled out through traditional means so that the implications could be understood by the public.” Our presence on Twitter didn’t take the place of structured rollouts with the Wall Street Journal; it didn’t supplant discussions with the New York Times editorial board; Twitter was an additional tool in our arsenal at a time when the media environment demanded it.

  The Bush messaging people certainly didn’t need to contend with Twitter. Things were different. Back then, Facebook practically still had a “the” in front of it. For us, Facebook was the way people communicated. Back then, memes were confined to funny cat things on weird websites. For us, memes were a political force. And, to me, they were fascinating.

  Political memes seemed to grow out of our ever-tightening time frames, our diminished attention spans, and Americans’ collective desire to be in on the political debate. Think about it. Few people read full articles these days—“Who has the time?” we say—but we inhale headlines and spout opinions. So political memes became a kind of headline in a picture. Like emojis, they’re a quick, compelling way to communicate. Often, they convey comedic commentary on a specific person. The first time I really grasped the power of
political memes was the legendary shot of a cool-looking, sunglasses-clad Hillary Clinton checking her BlackBerry. That image, captured by frequent pool photographer Kevin Lamarque, was worth a thousand memes. And it embedded this sense of calm, unflappability, and even a dash of panache in the image of Secretary Clinton. It was a permission structure to see Hillary as a little bit cool. It wasn’t entirely unlike the famous Obama Hope posters plastered around the country in 2008 (an analog meme). A tight image and defining word or phrase below, memes are essentially digital advertisements.

  Now, of course, memes can be negative, too. And some of the most viral memes were downright cruel—or played on an undercurrent of racism or misogyny. They were used to fan the flames of conspiracies or to push misinformation. Memes became so omnipresent and so influential that they were actually cited by Defense Secretary Robert Gates as a reason not to release the photos of a deceased Osama bin Laden: for fear that the images would immediately be turned into memes that could provoke a response.

  None of this is a surprise, given that memes are simply a way we communicate online. They weren’t ideal for a debate, though. That’s because memes fell into the category of social media discourse that, as Jason explained, was less likely to change minds than it was to shore up support or bolster beliefs. Still, they are an important part of the recipe for deepening sentiments and fueling enthusiasm, which is crucial when it comes to voter turnout.

  Shortly after almost seventy million Americans turned out to vote for Obama in 2008, he was faced with multiple inherited crises, and for a couple years, he was focused on combatting those and passing the Affordable Care Act. When I came aboard, things were stabilizing, but Americans didn’t seem to be noticing, and Democrats got wiped out in the 2010 midterms. Shortly after, the president made a comment about how one of his administration’s biggest failures was that we didn’t tell our story well enough, as we were too focused on policy and bogged down in crisis. Each department had an email distribution list that looked something like this: DL-WHO-Legal or DL-WHO-Research. After the president’s comment, I remember one of the speechwriters joking that they should change theirs to DL-WHO-BiggestDisappointment.