Fmr. FBI Director James Comey pleads not guilty at a historic arraignments. Lisa Rubin and Miles Taylor were inside the courtroom. And Jacob Soboroff is on the streets of Chicago, as National Guard troops roll into Chicago amid growing protest. Plus: The Senate struck down the same two short-term government funding measures today for the sixth time, extending the shutdown with no end in sight. Sen. Peter Welch joins to discuss the escalating standoff.

MSNBC reports The Trump administration's next target in its retribution campaign is Fmr. National Security Advisor John Bolton, following his targeted attacks on New York AG Letitia James and Fmr. FBI Director James Comey. Illinois AG Kwame Raoul joins The Weeknight to weigh in. Plus: House Oversight Committee ranking member Rep. Robert Garcia is demanding Jeffrey Epstein accomplice Ghislaine Maxwell testify "immediately" after the Supreme Court rejected her appeal to reconsider her conviction. He joins The Weeknight with the latest.