Photo by White House Photo Office

An Open Letter to President Obama

Before President Obama left office, his alumni association collected letters written by staff and volunteers from his campaigns and administration. We were asked to detail our personal journeys, to explain how working for him changed us, and to describe the impact we hoped to make. I’ve revised my letter here, lengthening it but trying to keep the spirit of the one I submitted in December 2016.

Dear Mr. President:

We’ve met just a handful of times. Only a couple of them could be considered meaningful interactions. Then again, during one of those, I forgot to tell you my name, so I’m not sure “meaningful” is the right word.

But I feel like I know you, and you know me, in a way that’s actually meaningful. I realized recently that it’s because our relationship began long before we met. We were hundreds of miles apart — you on a convention stage and me in my childhood home — but somehow, you made me feel as if we were in the same room.

In other words, I fell in love with you because of a speech. (I bet you get that a lot, huh?)

I fell in love with your vision for our country: a “tolerant America,” a “generous America,” a “beacon of freedom and opportunity.”

I fell in love with the way your descriptions of your grandmother in Kansas made me think about mine in Eastern Kentucky. The way your story of meeting a young man named Seamus in a VFW hall in Illinois made me picture my little brother, who’d been toying with the idea of talking to some military recruiters.

But mostly, I fell in love with your words. You articulated how I’d always felt about this country in a way that, up to that point, I’d only heard from Aaron Sorkin characters.

“In no other country on earth, is my story even possible.”

“That is the true genius of America, a faith in simple dreams, an insistence on small miracles.”

“Do we participate in a politics of cynicism, or do we participate in a politics of hope?”

Your words that night did more than just move me. They molded me.

When Time put you on its cover, I shoved it in front of my college roommates.

Look at this guy, I told them. He’s gonna be President.

They laughed.

Photo by Anna Humphrey

I joined your campaign understanding that I would be doing the kind of work that seldom lands people on the cover of Time, but that sometimes wins elections: knocking doors, making calls, recruiting volunteers. The kind of work, you liked to remind us, that you did on the South Side of Chicago.

Part of me secretly hoped that my bosses in Iowa would take one look at me and send me straight to Jon Favreau’s team in Chicago (the Seaborn to his Ziegler?). I’d loved writing since the first grade, you see, and I wanted desperately to learn how to do it from you. Or from the people you trusted to do it for you.

It didn’t exactly happen that way. Instead, I found myself in Hy-Vee Hall, watching you give the biggest speech of both our lives, the night we won the caucus.

“You know,” you began, “they said this day would never come.”

What an obvious line, I thought. What a perfect one.

In just nine words, you’d captured everything I’d experienced over the last seven months: the doubts of my family and friends, the skepticism I’d met at the doors, the wobbly hope of first-time caucus-goers. In those same nine words, you’d articulated the way Black Americans had been feeling for a lot longer than that.

You thanked all of us for “organizing and working and fighting to make people’s lives just a little bit better.”

You claimed we’d ushered in the moment “when the improbable beat what Washington always said was inevitable,” the moment “when we tore down barriers that have divided us for too long.”

Photo by Carole Fishback

I wanted to laugh and cry, to sing and shout. I think I did all of those things, hugging my Republican father and my newly enlisted brother and my fascinating, funny family of fellow field organizers. At some point, in the midst of all the celebrating, I made a silent vow to follow you to the ends of the earth.

You didn’t quite send me there, although Minot, North Dakota felt pretty close. On an all-staff conference call the day after we won the general election, you convinced me I should move to DC.

It took a long time and a lot of work, but I finally got the kind of speechwriting job I wanted. Not for you, but for the leader of a small foreign assistance agency.

This past summer, just a few months before you’d leave office, the White House asked her to give the biggest speech of both our lives at its first-ever Summit on Global Development. This one I actually wrote.

I tried to do what you did, to make at least one person in that room — whether she came from Kentucky or Kenya — feel like my boss was speaking directly to her.

And then, after my boss’s panel was over, you came on.

“Just a lot of do-gooders in one room,” you called us. You told us about your mom, a do-gooder in her own right.

You reminded us “how lucky we are to be living in the most peaceful, most prosperous, most progressive era in human history.” You told us about the plaque you keep on your desk, a constant reminder that “hard things are hard.” And you congratulated us on the progress we’ve made on some very hard things: the alleviation of poverty and disease, access to education and electricity, opportunities for women and girls.

Pay attention, I told myself after every sentence, or at least every paragraph. This could be it. The last time you see him speak, in person, as President.

As much as I love words — as hard as I’ve tried to make a living out of stringing them together — it’s difficult to describe how I felt in that moment. Humbled. Proud. Bitter. Sweet.

I have to admit, there’s been more bitter than sweet lately. I’ve worried, maybe even despaired, over the future of the work I’ve done, of the legacy you’ve built, of the country my brother serves.

But whenever I do, I try to remember — what else? — some of my favorite lines. From Dr. King. Or Edith Childs.

But mostly, of course, from you.

“Oh, what a glorious task we are given,” you said in Selma, “to continually try to improve this great nation of ours.”

A glorious task, indeed. The honor of a lifetime, in fact. To have done it for you. With you. From Iowa to India, and everywhere in between.

Of all the words I use to describe myself — sister, daughter, friend, writer — the ones I think I’m proudest of, the ones I want to carry forever?

Obama alum.

Photo by White House Photo Office

So thank you for giving me those words, and all the rest. Thank you for being a fighter, a hopemonger, an organizer. Thank you for teaching me how to bend the arc toward justice.

I’m honored to keep trying to do just that, in your name and alongside this open-minded, big-hearted family we’ve built.

And if you ever need a speechwriter, you know where to find me.


Anna Humphrey

In “Orations Worth Ovations,” professional speechwriters analyze great speeches (real or fictional, historic or personal) and explain what makes them so good.

Read then-Senator Obama’s 2004 Keynote Speech at the Democratic National Convention.

Read then-Senator Obama’s 2008 Iowa Caucus Victory Speech.

Read President Obama’s 2016 remarks at the White House Summit on Global Development.

Follow Anna and West Wing Writers on Twitter.



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