Donald Trump orders National Guard troops to Chicago and Portland, making good on his promise to generals to use American cities as "training grounds." Jon, Tommy, and Lovett discuss the court order—issued by a Trump-appointed judge—that blocked the deployment in Portland, the military-style immigration raids that rocked Chicago last week, and the signals that Stephen Miller and the rest of the Trump administration are sending about what's next for blue America. Then, the guys check in on the ongoing government shutdown, react to Trump's unexpected hint that he may be willing to negotiate with Democrats on healthcare subsidies, and discuss what it'll take for Prop 50—California's redistricting response act—to pass in November. Then, Ben Smith, Editor-in-Chief of Semafor and host of the Mixed Signals podcast, joins Tommy to talk about Bari Weiss taking over CBS News, the right's attack on free speech and Jimmy Kimmel, and the future of network media.

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