My Day at the White House after the 2016 Election
By: Kyle Herman
Tags: 2016 Election, 2020 Presidential Race, White House, Obama Administration, Correspondence

Our national redemption gave me the catharsis I needed to process a cycle of depression and anxiety that started exactly four years ago today. I’m finally ready to share my story from that day.

When Trump appeared to be winning after midnight on November 9, 2016, I was the only one still awake at my parents’ house in Ohio, where I’d spent the past four days getting out the vote. I asked on Facebook: “What to say to the millions of Americans who’ve been told they don’t belong here?” It wasn’t a rhetorical question. In my job at the Office of Presidential Correspondence, I was responsible for writing President Obama’s response to emails and letters from people across America looking for guidance, and for the first time I was dreading returning to work.

The first letter I ever wrote for Obama was to a man from Texas named Jashim, who was asking how long his family would have to live here, how many of his children and grandchildren would have to serve in the military and otherwise prove their loyalty, before they’d be accepted as American. I used Obama’s words to tell Jashim that being American wasn’t about what one looked like or how one worshipped, but about believing in our Constitution and America’s highest ideals. But then the voter tallies showed us that nearly half our country rejected these ideals and elected a demagogue who scapegoated people based on religion and race.

A chipper blond woman next to me on on my early morning flight asked if I was visiting DC, and I told her I lived there. She said I should be excited to be there at such an “interesting” time. I ignored her because I had no response for someone who likely just voted to prevent me from ever achieving the legal protections of marriage because of the way I was born. For the first time, I felt like a stranger in my own state.

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When I got to the White House, I went straight to our Email Team, with our army of interns and volunteers sorting through incoming messages. They were as devastating as expected: People with cancer and pre-existing conditions worried Trump would take away their healthcare; families scared they’d be torn apart by Trump’s immigrant purge; individuals scapegoated by attacks based on race, religion, gender, and sexual orientation, now worried about harm to themselves by emboldened hate groups or self-harm by loved ones who felt rejected by the American electorate.

Our Writing Team watched Hillary’s concession speech together, impressed by her conciliatory composure and her calls for unity despite winning more votes than the “winner.” A stark contrast to Trump’s refusal to concede four years later. Unlike Trump, Hillary’s campaign was never about her; it was about building a more hopeful and inclusive America. She was quick to pass the baton to the next generation, asking young people to “please never stop believing that fighting for what’s right is worth it… We need to keep up these fights now and for the rest of our lives.”

Obama gave a pep talk to some staff, trying to reassure them that our democratic institutions would constrain Trump and that he would not be able to undo the most significant progress we had made during his administration. Later that afternoon, he invited all the staff to public remarks in the Rose Garden to bring our country together and remind us the sun would keep rising. He said he’d heard in Trump’s victory speech and when speaking with him directly “a sense of unity; a sense of inclusion; a respect for our institutions, our way of life, rule of law; and a respect for each other. I hope that he maintains that spirit throughout this transition, and I certainly hope that’s how his presidency has a chance to begin.” I thought Obama’s “presumption of good faith” in Trump was dangerously naive at the time. But Obama didn’t seem to have a choice when he was trying to calm our fears; he predicted that the weight of the responsibility of the office would force Trump to take the job more seriously. But in 2020, with Trump trying to tear down our democratic norms and institutions, Obama would admit he’d been wrong.

But Obama also gave us reason to hope: “The path that this country has taken has never been a straight line. We zig and zag, and sometimes we move in ways that some people think is forward and others think is moving back. And that’s okay. I’ve lost elections before. Joe hasn’t.” Joe obviously hadn’t expected that shoutout, but he blessed himself with the sign of the cross, and then provided a welcome moment of levity by pointing out that wasn’t quite true if you counted the presidential primaries: “Remember, you beat me badly.”

Using Obama’s Rose Garden speech and other comments to draft a letter in response to the incoming mail, I wanted to emphasize that “progress hasn’t always followed a straight line” by adding “sometimes it’s two steps forward and one step back,” implying that two terms forward with Obama would be followed by one term backward with Trump. But as always, the Legal and Comms Teams prevented us from letting Obama sign his name on anything that could be interpreted as remotely political. In retrospect, they were right to do so; when Obama’s correspondence used that line after he left office, it was seized on by the press. And yet after the Obama Administration’s excessive caution to fact-check and self-censor every written communication to avoid even the appearance of impropriety, the Trump Administration has constantly violated the Hatch Act to use taxpayer dollars and properties for explicitly political purposes, including turning White House social media and comms into explicit partisan propaganda.

That same day in 2016 had more lessons for me about the media. Photos of my coworkers (and me if you look closely) were published by outlets labeling us “distressed and dismayed.” Trump supporters used the photos to mock the sadness we felt for Americans endangered by their destructive rhetoric and policies. They celebrated our “liberal tears” and proved, as they would for the next four years, that they’d rather “own the libs” than contribute to helping their fellow Americans, let alone themselves. They rejoiced in cruelty while failing to acknowledge that we weren’t sulking because “our team” lost, but because we spent every day trying to assist people whose cries would now be mocked or simply ignored.

As the sun set, a New York Times journalist came to my office in the attic of the Eisenhower Building. She was working on a story about the people who wrote to President Obama and our work to respond to them. She had spent much of the day with our Email Team as they reacted to incoming pleas for reassurance, and she wanted to know how I would go about writing the mass responses that would bear the President’s signature. She had observed me talking with my coworkers about the incoming messages, and she asked me how I was feeling. She opened up to me about how she was from Pennsylvania and was perplexed by the way her home state voted. I confided that my grandfather had died suddenly less than two months before, and the election outcome was like a repeat of that shock, except now it felt like we were mourning the death of America as a pluralistic democracy.

Although at that moment, I didn’t share Obama’s faith that our democratic institutions and values would constrain Trump, I explained that my job as a writer wasn’t to create new material, it was to “channel” President Obama’s thoughts and feelings in response to the incoming letters. I’d read Obamas books and studied his public statements and speeches, as well as his private correspondence to individual citizens (he read 10 letters a day and replied to some in his own handwriting and some with notes to our office to type a response). I was a glorified plagiarist; every letter I wrote had to be sourced to ensure it used language or sentiments already expressed by Obama elsewhere, and every fact had to be backed up by a U.S. government source. I oversaw a library of about 200 form letters on all sorts of issues people had written about.

That evening, I was struggling to write the letter I’d dreaded most, the one I’d hoped would never be necessary. I went through an outline of ideas about how it needed to affirm that our American democracy and values wouldn’t change, and that we shouldn’t give up hope and should stay engaged to hold our government accountable. I told the journalist that Obama was a better man for me for his gracious response to Trump’s win after Trump had launched his political career with the racist birther conspiracy and had spent his campaign spreading lies about Obama and promising to undo every good thing he had done. The outcome stung on a personal level because we had worked so hard to respond to the Americans who had written to Obama, and he had read and responded to more mail than any President in history. While Trump claimed he was giving voice to the “forgotten man,” Obama was actually the one listening to Americans from across the spectrum and working to help them every day. He’d never forgotten anyone; the only thing stopping him from doing more to help was Republican obstructionism in Congress.

I wondered aloud about how Trump’s election felt like a rebuke of our efforts to connect Obama to the American people, and for a brief moment it made me question if we had failed in our mission. I said it was really just “the bargaining stage of grief,” asking what we could have done differently and calling back to the way I’d felt when my grandfather died.

Weeks later, I found out White House Comms staff had heard through the fact-checking process for the article that I had allegedly said something to the effect of Obama being a “failure” or the cause of Hillary’s loss. Anyone who knows me knows I never would have said such a thing. While my memory was still fresh, I wrote down every detail I could remember from my conversation with the journalist, embarrassed that what I’d said could possibly be twisted that way. I’d been so cautious about not writing anything controversial on social media or talking to journalists at all until November 9 because anything a White House staffer says can be fodder for distracting from the President’s message, and I was ashamed that I’d let my guard down while I was in an emotionally vulnerable state. I’d chosen to speak freely because that day was bigger than me, it was part of history. But now I was worried that the article would distract from the letter writers and Obama’s responses.

Obama’s Chief of Staff Denis McDonough shared the article in the last tweet sent from his official account.

Those fears were relieved when To Obama with Love, Hate, and Desperation was published on one of the last days before the term expired. After reading it, Obama invited our Director of Correspondence to the Oval Office to thank her personally for her work, and he remarked that the story was his favorite article about his presidency. The journalist who wrote it went on to write an entire book about people who had written to Obama and his Correspondence Office. In it, she published the letter I’d been composing on the day we met.

Looking back at that letter before the 2020 election, it gave me hope that the thousands of people who received it had stayed engaged and were speaking out to help save American values. It’s been a long four years, but I’ve been inspired by the organizing and resilience in the face of injustices. Trump proved all our concerns about him were legitimate, and even now he is attempting a coup. But enough of us banded together to save our democracy, and while work remains to be done, we have earned the vindication America deserves and set our nation back on the path of striving toward liberty and justice for all.