Marc Caputo, senior politics reporter at Axios and one of the best reporters out there on the Trump beat joins Chuck to talk about reporting on President-elect Trump. Marc’s first story for Axios featured one of the hardest interviews to get in Trump’s orbit: an on the record discussion with Trump’s incoming chief of staff, Susie Wiles.

For the last alternative history episode of the holiday season, Chuck talks with former CIA Director John Brennan about a forward-looking scenario: What if Russia announced that they have a senior U.S. official on their intelligence service’s payroll. 

Alternative History: If George Washington ran for a third term, would the United States be here today? Chuck talks with Dr. Lindsay Chervinsky, presidential historian and the Executive Director of the George Washington Presidential Library.

Jeff Pearlman, author of "Football for a Buck," joins Chuck to talk about what might have happened if Donald Trump had been more successful in his attempt to buy the Buffalo Bill or bring the USFL to success.

Alternative history is back! We kick off this year's series with a look back at all the possible "What If" scenarios from the 2024 election. Chuck is joined by Politico's Senior Political Columnist, Jonathan Martin. 

Chuck talks with John Morgan, the founder of Orlando-based personal injury firm Morgan and Morgan with offices nationwide. Morgan, a well-known Democratic fundraiser in Florida, recently posted on Twitter that he was thinking of running for governor … as an independent. 

Detroit Mayor Mike Duggan joins Chuck to preview his independent bid for Michigan's 2026 gubernatorial election, in what could be a seismic shift in a battleground state.

Media reporter Paul Farhi joins Chuck to talk about his recent report for Northwestern Medill's local news initiative. In his piece, Farhi observed: “Donald Trump won the 2024 election with one of the smallest popular-vote margins in U.S. history, but in news deserts – counties lacking a professional source of local news – it was an avalanche.”

Martin O’Malley is the former governor of Maryland, mayor of Baltimore,  and most recently, the commissioner of the Social Security Administration in the Biden administration. In November, O’Malley launched a campaign to become the next chairman of the Democratic National Committee.

Sen. Chris Murphy (D-Conn.) joins Chuck to weigh in on the Democratic Party’s soul-searching since their election loss and President Biden’s pardon of his son, Hunter.