Never Ever Getting Back Together? The Trump/Elon Breakup

On with Kara Swisher

After reportedly speaking to President Trump on the phone, Elon Musk took to Twitter, on Wednesday, to say he regrets “some” of his tweets about President Trump — but that doesn’t mean all is forgiven. As the dust settles on last week’s cross-platform showdown, the long-term consequences from the breakup of the world’s richest man and its most powerful one are just beginning to emerge.

So, Kara gathered a panel of four expert guests to unpack how the feud ignited, who holds the most leverage, why a ceasefire took place, if it’ll last, and what it all means for the future of tech, politics and power. 

Henry Blodget is the co-founder and former CEO of and editor-in-chief of Business Insider. Before that, he was a tech analyst on Walls Stree. You can find him on Substack at Regenerator

Kirsten Grind is an investigative business reporter at The New York Times, the author of two books, and the winner of more than a dozen national awards. 

Kristen Soltis Anderson is a pollster, contributing Opinion writer for The New York Times, author, and co-founder of Echelon Insights.

Rick Wilson is a former Republican political strategist and ad-make. He is a co-founder of the Lincoln Project and you can find him on Substack or listen to his podcast The Enemies List.

Questions? Comments? Email us at on@voxmedia.com or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher.

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2025-06-12 53 min

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