A federal judge once again blocked the Trump Administration from sending the National Guard to Portland over the weekend — but if Trump is successful in the courts, Portlanders can look to the great city of Chicago for a preview of what may be in store. Since ICE began operations in September, there have been violent raids on apartment buildings and near-constant activity from aggressive federal agents rounding up immigrants who are being kept in facilities reportedly full of cockroaches and with horrifying examples of overcrowding. And, in some cases, US citizens are getting detained, too. Chicago Mayor Brandon Johnson has faced the brunt of Trump’s attacks on the city, while also reckoning with Chicago’s crime rate and affordability crises that many big cities also face. We sat down with the Mayor to talk about what it’s been like to face down the President while trying to manage the nation’s third-largest city. And in headlines, President Trump’s tariffs are at the Supreme Court this week, a rundown of the high-profile Election Day races, and 20 Democratic-led states sue the Trump administration over a rule that could block certain public servants from getting their student loans forgiven.