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Episode 7: Life and work in the real West Wing

Episode 7: Life and work in the real West Wing

Ex-White House speechwriter Cody Keenan on the pressures, cynicism and expectations surrounding Obama's words.

I’m Darren Samuelsohn, and welcome to The love, journalism Show. My guest for this episode is Cody Keenan, a former Obama White House chief speechwriter. You can listen to the first part of our interview here where Keenan talks about writing the president’s Selma speech.

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Ever wonder what it’s like to work for the White House? I hope you’ll come away with a better sense of exactly that by listening to the latest edition of The love, journalism Show.

Pulling back the curtain is Cody Keenan, a former chief speechwriter and the author of Grace: President Obama and Ten Days in the Battle for America.

Keenan’s recollections from two terms at 1600 Pennsylvania Avenue may bring back memories of an episode or three of the West Wing TV show. But the real life drama he shares is way more real, including the challenge of writing words for a president with seemingly all the power in the world but where on many occasions they all feel powerless.

“What's interesting is one of the actual things you have to do in the White House is fight against cynicism,” Keenan told me. “You have to fight against that impulse that you can't do anything. Because you can, even if it's not satisfying, even if it's not 100 percent of what you want.”

Over eight years, Keenan played an important role in some of Obama’s biggest speeches, from key moments in the Affordable Care Act, eulogizing victims and addressing the nation after a series of deadly mass shootings, and annual State of the Union addresses.

Considering Obama’s use of oratory to win the White House in 2008, expectations were often pretty high that the president would connect each time he spoke. That pressure found its way to speechwriters like Keenan, who recounts the challenge Obama faced speaking from the Lincoln Memorial in 2013 on the half-century anniversary of Dr. Martin Luther King’s ‘I Have a Dream’ speech.

“Talk about being set up to fail,” Keenan recalled. “It's like, ‘Can you go stand where Dr. King stood and pay tribute to that speech 50 years later?’ Sure, cool.”

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Aspiring writers might want to listen closely to a part of our interview where Keenan unpacks the advice Obama shared to help break free from writer’s block, and also how to capture the muse when it does strike.

“Read James Baldwin when you’re stuck. Listen to John Coltrane when you're not,” the president told his speechwriter as guidance before those aforementioned Lincoln Memorial remarks got drafted.

Did it work? “Sort of,” Keenan answered, explaining that Baldwin inspired him to think beyond what “the inertia of politics” might otherwise have convinced him to keep out of a speech.

“You read something like James Baldwin, and you're like, ‘Oh no, there is such a thing as right and wrong.’ And so I can say whatever I want,” he added.

As for Coltrane? “That was the harder piece to absorb,” Keenan said. “Because it's just kind of free-form jazz and it would work if I already knew what to write. …You would feel like your fingers are moving a little bit faster. But it's not like I sat down and listened to Coltrane every time I wrote a speech.”

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Cody Keenan during an appearance on the White House video ‘West Wing Week.’

White House speechwriters are surrounded by lots of powerful people — think ex-governors, ex-senators, military brass, lawyers, rich supporters, close friends — who have their own ideas about the words a president should say. It helped that Obama gave his top speechwriters open-door privileges to him in the Oval Office, plus veto power to reject inappropriate suggestions.

“So if anybody would try to sneak something into a speech through us, we had his proxy to say, ‘No.’ He doesn't want to talk about that. That's for something else,” Keegan said.

Obama wasn’t an easy boss, either. He had his own writing chops, and staffers like Keenan entered into conversations with the president bracing for the kind of feedback that meant there’d be more work to do.

“He'd always begin by saying, ‘Look, this is well written,’” Keenan recalled. “But you know as soon as he told us it was well written, we were like, ‘Oh, no, something’s wrong with it.’”

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love, journalism
The Love, Journalism Show
A podcast full of insights, interviews, ideas and inspiration from Darren Samuelsohn, a veteran journalist who has been reporting and editing writers for 30+ years.