PROGRAM

“Don’t talk to Whipple.” 

–Reince Priebus, Donald Trump’s former White House Chief of Staff, to his incoming chief Susie Wiles

Roosevelt House is pleased to welcome back one of our most popular guests, the bestselling author, journalist, and esteemed White House insider Chris Whipple—to discuss his latest book, Uncharted: How Trump Beat Biden, Harris, and the Odds in the Wildest Campaign in History. In this dramatic and revealing account, Whipple turns his eye to the historic 2024 presidential race—providing the definitive, insider story of what he calls the most significant political showdown in modern American history. He will be in conversation with author and MSNBC host, Lawrence O’Donnell.

A “disastrous” debate, a would-be assassin’s bullet, an eleventh hour candidate swap, surprising VP selections, charges of a stolen election, game-changing blunders—the history-making 2024 presidential election is a political saga, writes Whipple, of Shakespearean proportions. In minute-by-minute detail, Uncharted chronicles the unprecedented drama as it unfolds—documenting the stories of the Harris and Trump campaigns and the difficult, urgent decisions made in the back rooms of power, with the future of American democracy at stake.

Drawing on his unique access to exclusive sources on both sides, including conversations with members of the candidates’ inner circles, Whipple alternates between the Biden and the Trump camps, and tells the fly-on-the-wall story of each campaign. Taking readers behind the scenes of every headline-making moment, Whipple reveals how a post-debate “intra-party rebellion” forced Biden to step aside, how the nomination of Vice President Harris reshaped the race, and how she rallied excited voters across generations and demographics. In addition, Whipple provides startling new insights into how the Trump campaign overcame primary opponents and multiple prosecutions, rebranded Trump’s base to appeal to Gen Z voters, and forged alliances with Silicon Valley CEOs like Elon Musk.

An intimate portrait of American politics on the edge, filled with previously untold stories, anecdotes, and insights, Uncharted is the authoritative account of this pivotal chapter in American politics.

Chris Whipple is a New York Times bestselling author and widely acclaimed documentary filmmaker, speaker, as well as a Peabody and Emmy Award-winning journalist. He appears throughout the media and contributes to the New York Times and Washington Post, and has written for Vanity Fair, Politico, and the Daily Beast. This is his fourth appearance at Roosevelt House—the previous three were to discuss his books The Fight of His Life: Inside Joe Biden’s White HouseThe Spymasters: How the CIA Directors Shape History and the Future; and The Gatekeepers: How the White House Chiefs of Staff Define Every Presidency.

Lawrence O’Donnell is the host of The Last Word With Lawrence O’Donnell on MSNBC. Previously an Emmy Award-winning executive producer and writer for The West Wing, he also served as senior advisor to Senator Daniel Patrick Moynihan. He is the author of Playing with Fire: The 1968 Election and the Transformation of American Politics and Deadly Force: A Police Shooting and My Family’s Search for the Truth. 


Chris Whipple in conversation with Lawrence O’Donnell — Uncharted: How Trump Beat Biden, Harris, and the Odds in the Wildest Campaign in History | Posted on May 7th, 2025 | Book Discussions, Public Programs