Congress faces a November 1 deadline to extend Affordable Care Act subsidies. And Donald Trump is criticized for his relationships with autocrats. Plus, Lawrence shares some of his conversation with Rachel Maddow from the recent MSNBC Live '25 event. Sen. Sheldon Whitehouse and Amb. Michael McFaul join Lawrence O'Donnell.

MSNBC reports two federal prosecutors were placed on administrative leave at the direction of the Trump White House. Also, polls show a tightening race for New Jersey governor. Plus, the government shutdown threatens food assistance for 42 million Americans. And four Senate Republicans join Democrats to block Donald Trump's tariffs on Canada. Ken Dilanian, Rep. Mikie Sherrill, Rep. Jim McGovern, and Rep. Brendan Boyle join Lawrence O'Donnell.