Friday flashback — an Obama speechwriter speaks

What’s it like to write for a president? An Obama speechwriter visited his old business school last week and offered some advice.

an Obama speechwriter
Stephen Krupin’s profile photo on LinkedIn

Now, you’d hardly expect anyone’s speechwriter to bad-mouth the boss—at least not until all the post-Trump memoirs hit the shelves—but I believe Stephen Krupin when he says President Obama was “very easy to work with”:

“People who have only written for Barack Obama are spoiled and don’t know how good they have it.”

I didn’t expect to be moved to tears reading a student newspaper article. But Catherine Kim, Assistant Staff Editor of The Daily Northwestern (guess which school it serves) found the right quote from Krupin to describe the most memorable moment of his time as a White House speeechwriter.

In researching the president’s Memorial Day speech last year, Krupin interviewed veterans and their family members. One of the people he talked to, a woman who’d lost her husband in combat, asked if she could meet President Obama.

Krupin pulled some strings to get her seated in the president’s box at Arlington National Cemetery, where her husband is buried. And when the president mentioned her in the speech, the crowd broke into sustained applause.

“I will never forget that moment,” he said. “I wrote the speech. I could not sit here right now and tell you a single line in that, but I’ll always remember what it felt like when all of Arlington Cemetery stood and clapped for that woman.”

And no, I’m not crying—you are.

Seriously, folks, even when you have a great client, and by all accounts Obama is one, you sweat over the big speeches. You write and rewrite them so many times you think you’ll still be reciting them in your sleep 20 years later. It takes a powerful moment indeed to wipe all that work out of your memory.

An Obama speechwriter and his speech

So I went looking for that speech Krupin wrote. It’s strong, full of detail and stories. Grab some more Kleenex and read the story he’s talking about:

Joshua Wheeler’s sister says he was “exactly what was right about this world. He came from nothing and he really made something of himself.” As a kid, Josh was the one who made sure his brother and four half-sisters were dressed and fed and off to school. When there wasn’t food in the cupboard, he grabbed his hunting rifle and came back with a deer for dinner. When his country needed him, he enlisted in the Army at age 19.

He deployed to Iraq and Afghanistan — 14 times; earned 11 Bronze Stars, four for valor.  Last October, as ISIL terrorists prepared to execute 70 hostages, Josh and his fellow Special Ops went in and rescued them. Every single one walked free. “We were already dead,” one of the hostages said, “then God sent us a force from the sky.” That force was the U.S. Army, including Josh Wheeler.

Josh was the doting dad who wrote notes to his kids in the stacks of books he read. Flying home last summer to be with his wife, Ashley, who was about to give birth, he scribbled one note in the novel he was reading, just to tell his unborn son he was on his way. Ashley Wheeler is with us here today, holding their 10-month-old son, David. (Applause.) Ashley says Josh’s memory makes her think about how can she be a better citizen. And she hopes it’s what other people think about, too. Today, this husband and father rests here, in Arlington, in Section 60. And as Americans, we resolve to be better — better people, better citizens, because of Master Sergeant Joshua Wheeler.

The power of stories

It’s not just a story about Ashley Wheeler’s loss. Krupin and Obama don’t portray her as a victim. The story they tell focuses on what she has gained from the inconceivable hardship of losing her husband. And by extension, on what we all might gain from the sacrifice of the many military personnel whose stories never get told.

That’s why I love being a speechwriter. Even when you’re not an Obama speechwriter — even when you write for lesser mortals — you get to take the base materials of words and thoughts and sometimes alchemy happens and they turn into gold. A story you tell makes an impact, maybe changes the world just a little. It’s an extraordinary opportunity we have.

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“What am I building that lasts?” President Obama on legacy

President Obama told a great story about coming to understand the kind of legacy he could leave.

After he gave a speech in Cairo, the government flew him out for a private tour of the pyramids.

Seeing the pyramids in Egypt helped President Obama think about his legacy
Photo from

Here’s how he explained it to historian Doris Kearns Goodwin in last month’s Vanity Fair:

“…you’re going to these tombs and looking at the hieroglyphics and imagining the civilization that built these iconic images. And I still remember it—because I hadn’t been president that long at that point—thinking to myself, There were a lot of people during the period when these pyramids were built who thought they were really important. And there was the equivalent of cable news and television and newspapers and Twitter and people anguishing over their relative popularity or position at any given time. And now it’s all just covered in dust and sand…”

It helped him find perspective for his presidency. That what ultimately matters is not what anyone says or thinks in the moment. That’s not the stuff of legacy. Obama said:

“What is relevant is: What am I building that lasts?

And here in the United States, hopefully, what we’re building are not just pyramids, are not icons to one pharaoh. What we’re building is a culture and a way of living together that we can look back on and say, [This] was good, was inclusive, was kind, was innovative, was able to fulfill the dreams of as many people as possible.”

The legacy of “good, inclusive, kind, innovative”

The president had his sit-down with Goodwin before the election, when the values of goodness, inclusivity, kindness, and innovation seemed as solidly rooted in our culture as the pyramids are in the sands of Egypt. At least they seemed that way to many of us. Which is why the tide of vitriol and hatred the election unleashed just gobsmacked us. (By “us” here I mean straight white people, or those of us who unknowingly pass as same.)

But in a world that may pull us to build “icons to one pharaoh,” let’s remember that these icons always fade and fall in time. And the “pharaohs” who seem so important today will become specks in the sands of history.

Ancient Egyptians may have built the pyramids to honor their leaders, but today they stand as testament to the strength of thousands of people—not enslaved people, but privileged workers—who together built something that lasted. (See this fascinating article from Harvard Magazine on the construction of the pyramids.)

The culture of goodness, inclusivity, kindness, etc. that President Obama mentioned can live on in our hearts, and in our individual actions. Looking at each other—as Gloria Steinem said in my post yesterday—rather than at the pharaoh, we can maintain what’s important to us.

Language is at the heart of that. So I’ll keep writing; you keep reading.

Ad libbing: Leave this to the professionals

Sometimes ad libbing works—you know, getting carried away in the moment and going off script—and sometimes it leads you seriously astray. So this post carries a warning label:

Ad libbing is for pros only. Seriously.

Bill Clinton made a bad debut on the national stage, delivering a long and rambling, universally panned, nomination speech for the Democrats’ 1988 presidential nominee Michael Dukakis. Remember him? Exactly.

Clinton has given some absolutely forgettable speeches. He’s also given one of the best speeches I’ve heard in the last 10 years. How am I sure it was so good? Because four years after he gave it, I can still remember the feeling I had listening to it. It was like watching my Mets on their way to clinching the pennant: Even before he’d finished speaking, I knew it was going to get President Obama re-elected. It was a winner.

And much of it was unscripted. According to Dashiell Bennett (no relation) writing in The Atlantic, “[A]s an exasperated TelePrompTer operator found out,” the four pages of text given to the media “was really just a guideline to what Clinton actually wanted to say during his 49-minute address.”

As the Washington Post described  it,

After listening to him march through endless policy details, the crowd in Charlotte seemed to tire, and as he continued well past 11 p.m., the TV audience certainly may have drifted off. The speech went on and on and on, likely sending all but the fawning media off to bed. Clinton, let it never be said, is a disciplined speaker.

Editing or ad libbing?

The folks in charge of the convention tried to avert the never-ending speech by editing President Clinton’s prepared remarks. Was he ad libbing or did he just edit the deletions right back in, from his prodigious memory? In either case, the speech planned for 30 minutes (and that’s already 10 minutes too long for most audiences, in my opinion) grew nearly 60% longer.

Seriously, do not try this at home. Or at your next speaking gig. Conference organizers will be rightly miffed if you try. Very few people are as eloquent—or as irreplaceable—as Bill Clinton, and chances are you are not one of them. So write a tight speech and stick to the script and the time frame you’ve been given. You’ll deliver it better, too, if you’re not worried about ad libbing your way through.

This analysis from The Atlantic—which recently resurfaced on my Facebook newsfeed as a “memory”—shows exactly how Clinton’s written and spoken texts differed. And there’s a lot we can learn from it.

Like this passage, which exemplifies the thing I loved most about the speech as I watched it. He explained not just what would happen, but why it would have a positive impact on the American people:

Bill Clinton's additions and deletions in 2012 Convention speech

The “Explainer-in-Chief” added specifics (in green) and deleted a redundant reference, which is stronger placed at the end of the sentence anyway.

Below, he turns a passive verb active—no zombies here!—and added language that brings the issue to life more vividly.

Bill Clinton turns passive verbs active and adds detail

But here’s where the green additions really start flowing.

Ad libbing or editing? Either way the details make the speech come alive

Details! Yes, details take time—but without them, how flat would this passage be? Look again at what he was supposed to say:

When times are tough, constant conflict may be good politics but in the real world, cooperation works better. After all, nobody’s right all the time, and a broken clock is right twice a day. All of us are destined to live our lives between these two extremes.

It’s fine as far as it goes, but does it tell you anything about why cooperation works? About what cooperative government can produce? About the benefits to regular people when government works cooperatively? No, no, and no.

How did it play?

Mallary Jean Tenore, who at the time was managing editor of, summed up the reaction this way:

While called it “a fact-checker’s nightmare” and others criticized it for being too long, there’s something about Clinton’s speech that made it stand out: good writing.

(I added the emphasis.) See her analysis of the “10 rhetorical strategies” that make the speech work. I’d talk about them myself, but this is fast becoming the blog equivalent of a Bill Clinton speech.

Three things for you to remember here:

  1. People who seem to be ad libbing may not be. So don’t try it yourself!
  2. Interpolate a word or two if you must, but don’t add whole paragraphs on the spur of the moment.
  3. Respect the conference organizer’s time limits. Unless you’re a) Bill Clinton or b) prepared to not be asked back.

Clichés and how not to use them

Keep an ear out for clichés. No, not fashionable hats—those are cloches.Cloche hats—very different than clichés.

Clichés are fashionable too—if by “fashionable,” we mean that everyone uses them. But in the word-world, being ubiquitous is not necessarily a good thing.

Ever notice that when a tragedy happens, people flood the world with “thoughts and prayers”? A fine sentiment, and a fine phrase, but as one New York tabloid pointed out, thoughts and prayers don’t do much to stem a tide of violence. After The Daily News called out the empty “thoughts and prayers” rhetoric of do-nothing politicians, the phrase entered the red zone of phrases we can’t use without irony. Which may not be the total definition of cliché, but it’s definitely a subset.

Another common response to horror these days: “…there are no words.” This cliché fries me every time I see it—especially when it’s wielded by writers. Yes, I want to hiss, there are words. And you ought to know how to use them.

To clients, clichés seem like safe territory: Everyone else says it, so it must be okay. This always makes me think of my mother’s pointed question: “If everyone was jumping off the Brooklyn Bridge, would you jump off the Brooklyn Bridge too?” (Do regional variations of this question exist? Please tweet ’em if you got ’em.)

Countering clichés

It takes strength to buck the rhetorical tide and say something new. But if you want to differentiate yourself—if you actually want people to hear what you’re saying—you’ve got to make your own statement. Be authentic. Talk about your feelings, your reactions.

Instead of “there are no words…” try: “I can’t even begin to imagine…” or “I am angry…” or “I am sad…” That’s the other problem with this cliché, as well as “thoughts and prayers”—they’re both passive constructions. Real involvement demands active verbs: I will pray. I will do. I am outraged.

Nothing is more powerful than real emotion. Weren’t you moved when tears started running down President Obama’s cheek as he spoke about gun violence? You don’t need to give a speech to move people—the written word can do it just as effectively. But you do need to write about how you feel—don’t hide behind clichés.

“we are fellow Americans…”

This week’s issue of The New Yorker has a great exegesis of President-Elect Obama’s victory speech. (And yes, I know that word is usually reserved for religious texts.) But as great a night as it was, and as eloquent and moving a speech as it was – exactly what was needed at the end of a divisive campaign and the beginning of an era of historic change – for me, the most memorable speech-giving of the night happened an hour or so earlier, and half a continent away.

I did not vote for John McCain, but his concession speech was remarkable in its sincerity and humility. I can’t recall another concession speech in which the just-defeated candidate spoke so warmly and with such appreciation for the accomplishments of his opponent.

It reminded me of the John McCain I read about in a Vanity Fair article a couple of years ago*, talking in a speech about his imprisonment in Vietnam:

“Very far from here and long ago, I served with men of extraordinary character, honorable men, strong, principled, wise, compassionate, and loving men,” McCain told the students. “Better men than I, in more ways that I can number….Some of them were beaten terribly, and worse. Some were killed….Most often, they were tortured to compel them to make statements criticizing our country and the cause we had been asked to serve. Many times, their captors would briefly suspend the torture and try to persuade them to make a statement by promising that no one would hear what they said, or know that they had sacrificed their convictions. Just say it and we will spare you any more pain, they promised, and no one, no one will know. But the men I had the honor of serving with always had the same response, ‘I will know. I will know.’

“I wish that you will always hear the voice in your own heart, when you face hard decisions in your life, to hear it say to you, again and again, until it drowns out every other thought: ‘I will know. I will know. I will know.’ ”

If that John McCain had run in this election, the outcome would have been far closer – and perhaps not to my liking.

But at least that John McCain showed up on Election Night, to try to heal some of the divisions he and his campaign team exacerbated, and to point the way forward for us. The New York Times transcript captured it like this: ” ‘Whatever our differences, we are fellow Americans. And please believe me when I say no association has ever meant more to me than that.’ (Cheers, applause.)”

*Unfortunately, the Vanity Fair web site only carries an extract of this article. Look it up in the original mag – “Prisoner of Conscience” by Todd S. Purdum, February 2007.