Rick Wilson is one of the most well-known Never Trump Conservatives in the country, through his many TV appearances and NY Times best-selling book, “Everything Trump Touches Dies”. Rick and Roger discuss his new book “Running Against The Devil”, which gives advice to Democrats on how to beat Trump. Rick gives his take on the Dems chances in key red states, evaluates the pluses and  minuses of the remaining Democratic Presidential candidates, and more.

Rachel Bitecofer predicted the exact number of House seats the Democrats would win in the 2018 midterms before any other political analyst and she is already on the record as saying Trump will lose in 2020. Rachel and Roger discuss why Trump won in 2016 and why he likely won’t in 2020; why the Democrats won in 2018 (it’s not the reason many Democrats think); the truth about independent voters, and more.

Why Cities Lose traces the deep roots of the Urban-Rural divide in the U.S. and shows that geography is the main reason the left loses many key elections. Roger and Jonathan discuss how  Democrats are making inroads with suburban voters and which states that is happening in the most; the changing nature of college educated voters; how housing costs in major urban places may be unintentionally helping Democrats, and more.

American Bridge is the largest research, video tracking and rapid response organization in Democratic politics. They find what Republicans are hiding and make sure voters hear about it. Sacha and Roger discuss how American Bridge tracks Republicans and what they do with the video or info when they find something; how, according to their polling, Trump is vulnerable with his own voters; their $50 million campaign to flip Trump voters in key swing states, and more.

Charlie Sykes is one of the most well-known Never Trump conservatives. Roger and Charlie discuss whether Charlie considers himself a Republican anymore; whether the conservative movement can survive Trump; the issues Democrats should run on in 2020 to persuade moderate voters; Wisconsin as the key swing state and more. 

Roger & Jane discuss how she organized rural conservatives in Nebraska to oppose the Keystone Pipeline (Rolling Stone magazine called her “The Keystone Killer”.) They also discuss how Democrats can persuade rural voters; her rise from progressiver organizer to Nebraska Democratic Party Chair; whether Dems can win in Nebraska in 2020 and more.

Bill and Roger discuss key things liberals might find surprising: that virtually everything Obama signed into law got Republican votes; the NRA donating to politicians is not the real source of their power; that the Democrats may be making a political mistake pursuing single payer healthcare, and more.