I couldn’t sleep for shit.
Friday night had turned into Saturday morning, and I was staring at the ceiling in a hotel room in Washington, D.C., only blocks from the White House, recovering from my third hot shower of the night. The fever that had developed from an 11-hour Amtrak trip down the East Coast a day earlier hadn’t left my body, and the only way I knew how to deal with the chills was to take hot showers and hope for the best.
But that wasn’t the real reason for my insomnia and this body-zapping panic: I would be speaking to the president of the United States of America in 10 hours. On Air Force One. Before his speech in Selma, Alabama, on the Edmund Pettus Bridge to commemorate the 50th anniversary of the march that took place on what became known as Bloody Sunday.
On Monday, I had received an email from the White House offering “a potential opportunity with President Obama in the very near future.” The opportunity was to be a part of a roundtable of five journalists who would have 30 minutes to talk with the president.
As the week progressed, however, the stakes grew. With the date inching closer, the details became clearer. On Friday, the final email:
Following brief remarks at the top of the roundtable, the President will take a question from each participant.
As in one question. Zero room for error. My editor’s response was as blunt as it was true: “Better make it count.”
Lying in bed, staring at the ceiling, just a sunrise away from that one question, I still wasn’t sure what I was going to ask. I had written one question down, but I wasn’t convinced it was the question. And I was running out of time.
All I could think about was why I was here. Or, more accurately, what brought me here. I knew what I’d wanted to ask for years. I just didn’t know if, when the time came, I’d actually ask it.
I’ve been chasing Barack Obama for more than a decade. I watched his 2004 speech at the Democratic National Convention while deep in the throes of college application essays. It was a speech that I needed to hear, a speech that felt as if it were specifically for me. Before I knew it, I was working on Capitol Hill in 2007 as a college intern for Senator Ted Kennedy, where I would occasionally catch a glimpse of the then-Senator Obama traveling on the underground monorail from the Senate to the Capitol floor. I reveled in the excitement when he announced his presidency that February. I volunteered for that campaign in 2008 in New Hampshire, taking to the streets of New England with a megaphone following his victory, and hoping to one day be a part of his actual staff. In 2011, looking for a way out of graduate school, I applied for a job as a blogger in his reelection campaign — and I almost got that job, before then not getting that job.
My current job — the second attempt to drop out of graduate school — is a result of not getting a job with the Obama campaign. Living in New York is a result of not getting a job with the Obama administration. And my slow crawl away from politics and toward writing is a direct result of chasing — and never quite catching — the world that surrounds President Obama. The chase has felt never-ending. But in a way, I owe everything to the chase.
The chase was on my mind as I rode in a car to Joint Base Andrews on Saturday morning. It’s what I thought about on the shuttle to Air Force One with the four other journalists, Charles Blow from the New York Times, Zerlina Maxwell from Essence, White House correspondent April Ryan from the American Urban Radio Networks, and DeWayne Wickham, a USA Today columnist and dean of Morgan State University’s School of Global Journalism & Communication. And that chase is what I thought of when we arrived at Andrews and stood before Air Force One.
We were a diverse group. The age gap spanned 30 years, and we were from different parts of the country, with different levels of access to the president, different writing styles, different experience levels, and wildly different outlets. Each one of us had something specific we wanted from the experience, but as we boarded the plane, and then sat on the plane together and talked, it was clear that this was bigger than simply a coveted assignment.
In our part of the cabin sat five black journalists, preparing to talk to a black president — five black journalists that were greeted by the black senior adviser to the president, Valerie Jarrett, and black national security adviser, Susan Rice, all headed to the very black Selma, Alabama. This wasn’t normal. Yes, we each had our jobs to do when that moment finally presented itself with the president. But until then, there was time to just enjoy the occasion. We learned about each other, cracking jokes and telling stories. Some of us ran off the plane to take pictures of the First Family’s arrival. Others complained about Air Force One not having a Selma bootleg. Collectively, we shook our heads as we settled on the James Brown biopic Get on Up as our in-flight film.
Air Force One is a plane on PEDs. It rumbles with such force that we were told attempting to record the roundtable on our personal devices would be a challenge, and that the stenographer would have a transcript of proceedings ready for us later that day. In terms of size, it appeared to have swallowed two double-aisled commercial airliners. But it’s still a plane. It has wheels, it has wings, it takes off, and it goes into the air.
There were stairs everywhere, and so many rooms. And many of these rooms had doors. The floor plan felt like a labyrinth of narrow walkways, leading to beige area after beige area. Both times I left my part of the cabin by myself, I got lost. And even though I was never lost for more than 10 seconds, I immediately felt that let-go-of-your-mom’s-hand-at–Six Flags lost, scared that I was either going to get in trouble or never find my way back.
Every now and then, during a break in conversation, I’d retreat to my notebook and stare at my question. I’d written a second one focused on Selma, but it wasn’t right. It was a cop-out question. A question anyone could have asked. So I knew what I had to do. I needed to change a word here, move a sentence there, make it more concise, but I knew it was absolutely the type of question I was asked here to put forward.
Still tinkering more than an hour into the flight, we were alerted that we would be taken to a conference room in two minutes, and that we should get ready. The chase was back on. For a moment, I’d gotten so comfortable that I’d forgotten what the stakes were. I was just hanging out with my new friends. But just like that, we were walking through the cabin and into a conference room, and there was the president, ready to shake our hands. Once we sat down to talk, I was positioned at President Obama’s four o’clock, set to ask the third question, with Jarrett right over my shoulder. I stared at my question, wondering if I should have worn a tie, desperately trying to figure out what to do with my elbows. Leaning on the table feels sloppy, but I need to lean in to listen and the table really helps with that. But what do I do with my hands? And is my mustache curling into my mouth?
As President Obama began his opening statement, chief official White House photographer Pete Souza roamed the room. I was listening, still thinking about my question. As the White House veteran, Ryan1 went first. I paid attention to how she asked her question, how long it took, and whether it overlapped with mine. Hers concerned the president’s place in history. Following Ryan, Maxwell asked about the Department of Justice’s Ferguson report. These were good questions, and they made sense leading up to President Obama’s speech in Selma, all of which only increased the stress I’d placed on my question. I felt proud — we were a team in this conference room, and they’d pulled their weight. As he finished answering Maxwell’s question, the president gave her a smile, rotated a bit, and looked directly at me.2
Mr. President, so since you were — since I was in college, which is when you were elected, I’ve watched everything you’ve had to go through — jumping through hoops, going over hurdles, everything. And there’s been a common notion amongst my peers — peers who were very interested in getting into politics, being politicians, even that — this idea of if Barack Obama can’t say or do what we think he wants to say or do as President, then could any of us ever do that if we get into politics, be it about Ferguson, about gay rights — any of these things where we feel we know what he wants to say, but he can’t really do it at that moment.
Is that a sentiment that you are commonly aware of? And does it at all inform kind of how you want to wrap up your presidency? And I guess if you were trying to advise someone in this climate that wanted to make some change or have an immediate impact, would you advise them into getting into politics?
Well, I mean, let me say a couple things about that. First of all, one of the things I’m very proud about, from the time that I ran for the U.S. Senate to me running for President to being President is I’ve said what I meant. I haven’t engaged in a lot of editing. Now, I don’t always say it the way I might say it if I’m sitting over at the dinner table with Michelle. I might not say it the way I say it if I’m on the basketball court with some of my buddies. But the trajectory of what I’ve said, what I care about around policy, I haven’t had to bite my tongue. I think that’s a mistake.
A lot of times where this comes up in the African-American community has been the notion of, well, he hasn’t just said this is racist, or he hasn’t just called out what somebody did, or he hasn’t specifically talked about why the African American community as opposed to poor folks or middle-class folks generally need help, and hasn’t targeted enough the racial problems in this country. And I’ve answered that publicly as well, which is I am the President of all people, and if I pass legislation that is boosting their income tax credit for low-income workers, I know by definition that African Americans will be disproportionately helped by that.
The notion that I would describe that as a bill targeting African-Americans not only does not get — help it get passed, but it also then ignores all the white folks who are also struggling, and all the Hispanic folks who are also struggling. And my job is to build coalitions of like-minded people who care about the same issues I care about.
When it comes to issues of racial justice around — that are very specific around criminal justice, whether it’s Trayvon or Ferguson or other circumstances, I have been very forward-leaning, with the exception that I have not commented on active investigations or potential prosecutions. The reason for that is not because I’m self-editing, the reason is the formal role I have. Eric Holder is my boss — or I am Eric Holder’s boss. The prosecutors who are investigating the cases report to Eric Holder, and if it looks like I’m putting thumbs on the scale, that can have an adverse impact on the resolution of these cases.
Now, to go to young people generally, and how they might think about public service, I don’t think that politics is the only way to serve. You can write a great book. You start a wonderful business. You start a non-profit. You’re a principal or a teacher inside a school that’s doing a great job. Those are all meaningful ways of advancing the cause.
But we can’t ignore politics. That’s how we make determinations about our institutional arrangements in this society. That’s how resources get allocated. That’s how we decide whether a school gets money or a young person gets a student loan, or a young private gets sent to war and how he or she is treated when they come back, or whether we’re going to protect our seniors from economic insecurity when they retire. Those are all political issues, and to avoid them makes no sense.
And the notion that there are going to be times where you have to compromise in politics suggests that you don’t have to compromise at Grantland, or you don’t have to compromise as a businessperson. That’s more a reflection of young people, thinking you can do whatever you want. The truth of the matter is, is that we live in a society where you got to work with others and not everybody is going to agree with you all the time. And the more your influence expands, the more a diverse set of people you’re going to have to deal with. That’s a skillset you’re going to need no matter what.
This was the only moment on the morning of March 7, 2015, when I was completely at ease. The moment when the president and I were talking. As soon as it ended, I realized I’d actually asked the question and that he’d actually responded. It felt right. As the roundtable continued, we began our descent, and I kept thinking about how bizarrely normal it all felt. Being in the plane. Being in the room. Attempting to challenge the president and the president challenging me back. I’d long thought my twenties would be defined by getting sonned by the president.
I wasn’t excited anymore. I felt oddly reserved — mostly because I felt so comfortable.
As the plane touched down, the president was still answering the final question, from Blow. It was clear we needed to leave, but the president was not done. Everyone in the room braced the contents of the table to prevent them from sliding off during the landing, but the president kept on answering, as if nothing were out of the ordinary. His unflappability is an art. He never got defensive, even as he defended himself. He never raised his voice, and he never rushed his thoughts, occasionally pausing to make sure he was saying exactly what he intended.
More than five minutes after we’d landed, the president finished his last answer, thanked us, and left. The moment he walked out of that room meant it was a race to get off Air Force One as quickly as possible.
The president was behind schedule and we weren’t even in Selma yet. We’d just landed in Montgomery. In order to get to Selma, we had to take helicopters.3
My easy-to-stir motion sickness never reared its queasy head during the 20-minute helicopter trip to Selma. I wasn’t even ready to think about the city yet, and that was the entire point of the trip.
After we landed, we took a motorcade to the bridge. When you ride in a presidential motorcade, you realize that the Obamas have not been in traffic since January 2009. Nothing breaks the rules quite like a presidential motorcade. Everything you know about the laws of traffic do not apply. All that matters is the pavement that connects Point A to Point B. Weaving through Selma, however, my awe at the audacity of the motorcade quickly receded as I took in the scene. The people of Selma. There were people everywhere.
James Patterson/AP Images for Grantland
Someone in the car compared the scene to Ali in Zaire. The people in the streets were running at the motorcade, waving at the 40-plus vehicles as if the Olympic torch were coming through town. At this distance from the bridge, none of these people would make it to hear Obama’s speech. So this was their moment, to see a car carrying the president of the United States as he came to town for the first time since 2007.
The pure joy of the crowds temporarily made me forget the horror that inspired this jubilee — that people flock to Selma every year as a reminder of this country’s ugly past, as well as in remembrance of those brave men, women, and children who risked it all so this stain on American history would be seen by all, in hopes that it would never repeat itself.
That history coursed through my mind as our car began to drive up a hill. Before I knew it, we were on the Edmund Pettus Bridge.
James Patterson/AP Images for Grantland
“Oh my Jesus,” Ryan said. And for good reason. On the other side of that bridge were the people. People as far as you could see — as far as people could be. The moment was breathtaking — for the first time all day, no one was talking. For a few seconds, all you could do was look out and think about what happened on this bridge; consider the significance of the speeches that would be taking place in front of this bridge, and who would be making those speeches; pause to think about what it means that Congressman John Lewis would again introduce Barack Obama in Selma, only instead of in a church, this time it would be just feet from where he was attacked and his skull was fractured 50 years prior.
We drove toward the throng, then took a left off the bridge. And just like that, it was over. The events in Selma were only beginning, but once I got out of that car and entered the press area, I was no longer in any capacity with the White House. In a flash, everything went back to normal — my normal.
Suddenly, all my problems were mundane again. I had to charge my phone through a laptop on a bush under a set of metal bleachers. I spotted quasi-celebrities and smirked. I stood, disappointed by the modest amount of emotion in the press area, as rousing speech after rousing speech was delivered. I watched Barack Obama speak from a distance. We were apart again. His speech would be met with widespread praise and some criticism. As I was watching, I vacillated between feeling inspired and frustrated, passionately applauding and then folding my arms. Once again, I was a bystander of the political machine.
James Patterson/AP Images for Grantland
I couldn’t stay awake for shit. But when I finally woke up, I was angry.
I was gripping the armrests of 23D and 23E, face tight, body stiff. It was Sunday evening and I was flying from Atlanta to LaGuardia. I was seething, because a dream I’d long suppressed had resurfaced with a vengeance: I’d wanted to be Obama’s speechwriter.
I’d wanted it so badly for years, and when it became clear it never was going to happen, I’d buried it deep. It’s what I do when I want to forget I’ve failed — I simply put it in a folder within a folder within a folder in my brain. Flying to New York — the place that represented not getting that job — it reemerged. And it wasn’t going anywhere until I dealt with it.
Had a track toward that job presented itself, everything would have been different. My years in New York would not exist. I’d never have met so many of my closest friends. Four years of writing, gone. I knew all that. I’d internalized it, and still I was pissed.
I’ve spent my entire life watching people who have had successful lives still get misty-eyed about blowing out that knee and never going pro; about coming up short and not qualifying for the Olympics; about not scoring high enough on that test to get into that school. People who have had more impactful lives because they came up short. People who will tell you that, ultimately, they’re happy they came up short. But people who will still openly admit it’s something they think about all the time.
This was that. The shock of Saturday morning ran through my system for 24 hours. I expected it to finally give way to relief and to joy. But instead, this was anger.
And I liked it, because I knew it meant I still cared. In that moment, I finally got the answer to the question I’d spent so many years wanting to ask the president. I wasn’t chasing Obama — he was a smoke screen. I was chasing political enchantment. Even if that wasn’t exactly what I’d gotten from Obama, he’d helped me get there. And as we descended into LaGuardia, that anger finally gave way to elation.