Republican pollster Whit Ayres explains why he’s pessimistic that President Trump can win again, talks about the opportunity for Republicans to solidify support in Florida and explains why Lindsey Graham (his longtime client) has become a Trump loyalist. 

Matt Lewis, conservative columnist for The Daily Beast and CNN political commentator, explains why there's no presidential candidate he can support in 2020, reminisces on his work for Tucker Carlson and expresses his disenchantment with Nebraska Sen. Ben Sasse.

Ian Russell, a principal at consulting firm Beacon Media and former deputy executive director at DCCC, talks about the politics of health care, how Bernie Sanders presents a risk for House Democrats, and his skepticism of Joe Biden's 2020 journey.

Democratic pollster Jill Normington, of Nomington Petts, gives Trump better than a 50 percent chance at winning the election, discusses the gains former Vice President Joe Biden will make early on if he decides to run, and what it means to be an "and" candidate.

Halie Soifer, the executive director of the Jewish Democratic Council of America, addresses Rep. Ilhan Omar's (D-MN 05) anti-semitic comments, "Jexodus," and the Iran Nuclear Deal.