Start Me Up: Greg Olear
1h 2m | Aug 20, 2026Greg Olear is back! He's the author of Rough Beast, PREVAIL columnist & podcaster, and co-host of The Five 8 on YouTube.
Topics: Greg and I talk about what Democrats need to do differently heading into the next election, including the need for candidates who aren’t tied to the party establishment. We discuss Jon Ossoff’s appeal, the danger of primary infighting, and whether Democratic leadership is prepared for the election interference and cheating we expect from Trump and his allies.
We also get into possible responses, from using the 14th Amendment to disqualify Trump to expanding the Supreme Court and making Puerto Rico and D.C. states. Along the way, we talk about the rise of DSA candidates, the state of the USS Abraham Lincoln, the media’s changing role, the growth of independent media, and why I’m feeling optimistic about a potential blue wave in November.
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