Our guest for Five Questions tonight is Jon Favreau, President Obama’s chief speechwriter from 2005-2013, cofounder of Crooked Media (newly on Substack, find them here), cohost, along with fellow Obama aides Jon Lovett and Tommy Vietor, of the popular Pod Save America, and coauthor of the 2024 book Democracy or Else. That’s a lot! But I wanted Jon to join us tonight, specifically to share his experience as a speechwriter who is adept at helping American voters connect with their better angels to see how we can channel that today. Remember the “Yes We Can” speech and Obama’s inaugural addresses? It’s such a stark contrast to Donald Trump’s communication style, if you can even call it that. Tonight, Jon shares his unique perspective on where we’ve been, where we are today, and what we can do next.
Jon lives in Los Angeles with his wife Emily, their sons Charlie and Teddy, and their dog Leo. “Five Questions” is a feature for paid subscribers, my way of thanking people who support this work and make it possible for me to devote the necessary time and resources to it. But please know that whether you’re a paid subscriber or not, I’m very happy to have you here! I appreciate everyone who reads the newsletter and works to keep themselves and others informed in this pivotal moment. Continue reading this post for free in the Substack app
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Friday, October 31, 2025
Five Questions with Jon Favreau
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