From Obama’s Jokes to Surfboards: David Litt on Winning Hearts & Votes | Lincoln Square
August 4, 2025
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37:40Now PlayingFrom Obama’s Jokes to Surfboards: David Litt on Winning Hearts & Votes | Lincoln Square
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as posted by the channelWhen Trump tells a story — or what one might call a story, but is really just a kind of jumble of language punctuated by absurd turns and the occasional grunt — his fans follow it. They love it. He’s like the comedian who breaks open the world for them and examines the insides in a way that is both surprising and relatable (to them).
He’s speaking their language, in other words. We might see his speech as hate-filled (it is), confusing (yes, yes, yes), contradictory (it isn’t not contradictory), and so on. But it creates connection with his base.
I know it’s always popular and necessary to dunk on Dems in pieces like this, but the truth is the Dems at the top of the party have had a hard time fostering deep connections between themselves and the people they hope to represent. They do not entertain. They explain. And it’s pretty hard to explain and listen at the same time.
David Litt is a former Obama speechwriter and joke writer, and his new book, It’s Only Drowning, is about his experience learning how to surf with his brother-in-law, Matt, an electrician and a big fan of folks like Joe Rogan. The book is hilarious, and you should read it (you won’t be the first — it’s a bestseller). But, in some ways, it’s a book about connecting and connection — with nature, with oneself, and with people outside of your political tribe.
Dems would do well to listen to their audience, and some certainly do. However you feel about Democratic mayoral nominee Zohran Mamdani’s policies, the fact that he had the audacity to ask New Yorkers what they were concerned about, and then hear them out seems like an obvious, very human thing to do, but it’s a tool that most Dems have yet to develop.
Think about a comedy writer or comedian or, well, Trump. They are able to deliver a message and gauge the response of their audience at the same time. They craft their message based on the feedback from their people.
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