President Biden secures the release of four U.S. residents in the largest prisoner swap since the Cold War. Also, Donald Trump doubles down on attacking Harris' racial identity. Plus, the economy and reproductive rights are likely to be key issues for Wisconsin voters. And the presidential race could be key for down-ballot races. Sen. Chris Coons, Rep. Shontel Brown, Mayor Ken Budge, Sen. Tammy Baldwin, and Gov. Jared Polis join Jonathan Capehart.

Donald Trump struggles to campaign against Vice President Kamala Harris. Also, the Supreme Court rejects Missouri's bid to block Trump's sentencing and gag order in the hush money case. Plus, The Washington Post reports a $10 million cash withdrawal drove a secret probe into whether Trump took money from Egypt just days ahead of the 2016 presidential election. And a recent poll finds 49% of voters believe Trump does not have the mental and cognitive health to serve as president. Sen. Laphonza Butler, Andrew Weissmann, Barbara McQuade, and Simon Rosenberg join Lawrence O'Donnell.