Jen Psaki breaks down Trump's cash problems and his ongoing grift-- using other people's money to cover his personal legal expenses. House Speaker Emerita Nancy Pelosi joins Jen to outline the stark differences between the chaos reigning the GOP and the accomplishments uniting the Democratic party. Jen is also joined by Ambassador Michael McFaul to discuss Vladimir Putin's baseless attempt to shift blame for a deadly terrorist attack from ISIS to Ukraine. Next, legal experts Andrew Weissmann and Neal Katyal join to discuss what to expect in Trump's criminal trials ahead of the bond deadline in his fraud case. Later, Kara Swisher joins Jen to discuss her new book, "Burn Book: A Tech Love Story", including Elon Musk and his echoing of Trump's threatening immigration rhetoric. Finally, Jen is joined by veteran political reporter Amy Chozick to preview her new show on MAX, "The Girls on the Bus," which follows four women journalists on the campaign trail.