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. CHECK OUT THESE DEALS FROM OUR SPONSORS SIMPLISAFE: https://www.simplisafe.com/CROOKED ROCKET MONEY: https://www.rocketmoney.com/crooked ZIPRECRUITER: https://www.ziprecruiter.com/CROOKED BETTERHELP: https://www.betterhelp.com/psa CHAPTERS 0:00 - Intro 0:40 - Trump's War on blue cities 24:29 - Politics of Trump's War 27:54 - Bad Bunny playing the Super Bowl 32:32 - Ad break 35:14 - Government shutdown continues 48:30 - Prop 50 59:24 - Ad break 1:02:30 - Ben Smith interview Join this channel to get access to perks like ad-free episodes and exclusive videos: https://www.youtube.com/channel/UCKRoXz3hHAu2XL_k3Ef4vJQ/join Get tickets to CROOKED CON November 6-7 in Washington, D.C at crookedcon.com Subscribe to our channel! https://www.youtube.com/crookedmedia?sub_confirmation=1 Photos courtesy of AP Photo Archive Crooked believes that we need a better conversation about politics, culture, and the world around us—one that doesn’t just focus on what’s broken, but what we can do to fix it. At a time when it’s increasingly easy to feel cynical or hopeless, former Obama staffers Jon Favreau, Jon Lovett, and Tommy Vietor have created a place where people can have sane conversations that inform, entertain, and inspire action. In 2017 they started Crooked with Pod Save America—a no-bullshit conversation about politics. Since then, we continue to add shows, voices, and opportunities for activism, because it’s up to all of us to do our part to build a better world. That’s it. End of mission. Learn more about Crooked at http://www.crooked.com Follow the pod on Twitter https://twitter.com/podsaveamerica Follow Crooked on Facebook https://www.facebook.com/CrookedMedia/ Follow Crooked on Instagram https://www.instagram.com/crookedmedia/