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The former Director of Speechwriting for President Barack Obama is now hosting one of the most popular political podcasts right now. Not a typical career path for a speechwriter. But it’s not like Jon Favreau (no, not that one) ever had much of a typical career to begin with anyway.

After cutting his speechwriting teeth during Senator John Kerry’s 2004 presidential campaign, Favreau joined Obama’s team in 2005, and became his chief speechwriter in 2006. When Obama assumed the presidency in 2009, Favreau was appointed Director of Speechwriting and became the second-youngest chief White House speechwriter, after James Fallows, who wrote for President Jimmy Carter.

Favreau would spend the next four years in the White House, working closely with Obama, before leaving in 2013. He cited burnout and the desire to pursue other ambitions, which included consulting screenwriting, launching communications firm Fenway Strategies with former Obama spokesperson, Tommy Vietor, and contributing to various outlets, including writing for The Daily Beast and hosting Keepin’ it 1600 on The Ringer podcast network.

Despite trialling out several new career options, it was in podcasting where Favreau found his next calling. In 2017, together with Vietor and Jon Lovett, another former Obama staffer, Favreau founded Crooked Media, a podcast network which hosts over 10 political podcasts including the company’s flagship show, Pod Save America which averages more than 1.5 million listeners an episode.

You’re trying to balance what the president would want to say with what people are looking to hear. But you need to strike the right balance, because if it’s all what people want to hear, that’s not true to who he is.

Departing Obama Speechwriter: ‘I Leave This Job Actually More Hopeful’ | NPR

Working as Obama’s speechwriter for close to 10 years, Favreau was responsible for crafting several milestone moments, including the president’s first inaugural speech, the first and second State of the Union address, as well the “Yes We Can” slogan.

“He has become a friend and a collaborator on virtually every major speech I’ve given in the Senate, on the campaign trail, and in the White House,” Obama said in a statement about Favreau’s departure from The White House.

It was never an easy task, crafting words for perhaps one of the most successful political orators in history; someone who was launched their political career with a speech at the 2004 Democratic National Convention and who had also published two best-selling books before he was elected president. But the two men formed a special bond over words and ideas. Obama even referred to Favreau as his “mind reader.”

“Barack trusts [Favreau],” said David Axelrod, former Senior Advisor to Obama. “And Barack doesn’t trust too many folks with that – the notion of surrendering that much authority over his own words.”

Often times, the president and his speechwriter would sit together for hours, Obama talking and Favreau taking notes on his laptop. Favreau will then go off to write the first draft of the speech and send it to Obama to work on it. The two will go back and forth with this process until the speech is finalised.

A GQ profile gave readers a glimpse into Favreau’s writing routine:

Favreau’s method was that of the student having an essay crisis. He would withdraw with his laptop to a nearby Starbucks, take off his Aviator sunglasses and pound away for hours – a process he called “crashing”. Even now, more soberly dressed and with a formal White House title, at the helm of a team of six writers, he sometimes disappears to a Washington coffee shop for peace, caffeine and concentration.

Jon Favreau has the world’s best job | GQ

“My challenge is to make sure that whatever he’s thinking, whatever thoughts he has, we can get them down on paper, and we can shape the words to basically what he really wants to say,” Favreau told NPR.

“And then we’ll start going back and forth. Sometimes he will just make line edits himself and send the draft back. Or sometimes he will want to take the speech in an entirely different direction, and he will write six or seven pages of scrawled handwriting on a yellow legal pad, and we’ll go back at it that way.”

During busy writing periods, Favreau often worked on speeches until 2-3am, drinking double espressos and Red Bull to get through the early hours of the morning. It wasn’t rare for him to then wake up at 5am for another 16-hour day.

In 2009, Obama kicked off his first official Asian tour with a speech in Tokyo. Speaking to Boston Magazine, Favreau described the laborious process of getting the speech written up and approved:

The speech was written over the last couple of weeks. Terry Szuplat started it at headquarters. Some people stopped [at a refueling point] in Alaska, got out, hung out there. But we stayed on the plane and had a group editing session where people sat around a table, went through the speech line by line, and told us what they liked and what they didn’t. So that’s always real fun for us. The president edited it after that, had a few line notes, which I’m holding right here. And then we sent it off and it was done.

Obama’s Ghost | Boston Magazine

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