Al Cardenas, the former chair of the Florida GOP and worked on President George W. Bush’s campaign, and Obama’s White House Communications Director, Jennifer Palmieri, join Chuck to talk about the first Trump-Biden debate.

NBC News Correspondent Leigh Ann Caldwell talks to Chuck about the steps the Senate is taking to replace the late Supreme Court Justice Ruth Bader Ginsburg. David French, senior editor at the Dispatch, discusses the long-term implications of Republicans' flip-flop on late-term court fights.

A peak at Russia's cards during the next election with former FBI Counterintelligence Officer Peter Strzok and Scientific American Editor in Chief Laura Helmuth discusses the publication's decision to endorse a candidate for the first time in 175 years.

Chuck talks with polling heavyweights Charlie Cook and Larry Sabato to talk about the election now that we are eight weeks out. Maria Teresa Kumar updates Chuck on Latino outreach from both campaigns.

Brian Stelter, chief media correspondent at CNN and author of "Hoax" joins Chuck to talk about Fox News. Will Sommer from the Daily Beast and Ben Collins from NBC News explain what's really going on with Qanon.

Chuck talks with Politico Magazine's chief political correspondent, Tim Alberta, and staff writer at the Dispatch, Sarah Flores. Plus, a conversation with Congressman Denver Riggleman about the ways his party has changed.

Olivia Nuzzi reported a must-read look inside the Trump campaign, for New York Magazine. NBC News Political Unit reporter Ben Kamisar updates on ad-spending and Steve Kornacki reacts to the first nights of the DNC.

NBC News Senior Washington Correspondent Andrea Mitchell and NBC News Political Embed Deepa Shivaram join Chuck to talk about Sen. Kamala Harris. Washington Post Sports Columnist Sally Jenkins discusses the changes to the fall college sports season.

Dave Wasserman, House editor for the Cook Political Report, and Abby Livingston, Washington Bureau Chief for the Texas Tribune, join Chuck. The Knight Foundation's Sam Gill and former Missouri University professor, Barbara Cochran talk about a new report on trust in the media.

In one week, one of the decisions that could have the most impact on the race is reportedly set to be announced: Biden’s VP pick.