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.

Ben Wikler, chairman of the Democratic Party of Wisconsin, talks to Chuck about his campaign for the DNC chairmanship and what he thinks unites the party. Wikler also discusses President Biden's pardon of his son, and why he thinks Democrats lost on Election Day.