Republicans are scrambling after learning their proposed cuts to Medicaid, which would offset trillions in tax breaks, violate Senate rules. Reps. Ayanna Pressley and Sydney Kamlager-Dove join The Weeknight to break down what this could mean for Americans. Plus, Senator Chris Van Hollen discusses what he sees as a dangerous lack of transparency from the Trump administration in the Middle East. And Congresswoman LaMonica McIver is vowing to fight the Trump DOJ for as long as it takes.

Sen. Amy Klobuchar joins The Weeknight to discuss Senate Republicans' desperate push to get Trump's tax bill over the finish line. Plus, Chair of the Democratic National Committee Ken Martin shares his new plan to fight the President's agenda – and start winning more elections.

In the second hour of Monday's edition of  The Weeknight, Rep. Debbie Dingell and Sen. Tammy Baldwin break down the GOP's tax bill and what it could mean for millions of Americans' health care and the national debt. Plus, George Conway explains the far-reaching implications of Trump's monumental Supreme Court win on birthright citizenship.