In which John Heilemann talks with Claire McCaskill, former two-term Missouri Democratic senator and current political analyst for MSNBC. Heilemann and McCaskill discuss the Senate passage of Joe Biden's $1 trillion infrastructure bill and its outlook in the House, along with his proposed $3.5 trillion expansion of the social safety net; whether Biden is doing enough to press for voting rights legislation in the face of a slew of GOP efforts to curtail them; an array of gender-tinged topics, from Andrew Cuomo's resignation and McCaskill's own #MeToo experiences as a young state legislator to the epidemic of sexual assault in the military (an issue she sought relentlessly to address in her time in the Senate); and politics in the Show Me State, including the futures of ultra-conservative Senator Josh Hawley (who defeated McCaskill in 2018) and ultra-progressive St. Louis congresswoman Cori Bush. McCaskill also waxes hopeful about the playoff prospects of her beloved but underperforming St. Louis Cardinals, and professes her (as yet unrequited) love for Charles Barkley.


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Claire McCaskill

Living in America these past few years has been like living in a movie—a mashup of Blade Runner, A Clockwork Orange, and Idiocracy, that is. The never-ending pandemic, the routine mass shootings, the climate literally and figuratively on fire; the economy first battered by recession, then ravaged by inflation; an angry electorate, armed to the teeth and addled by conspiracy theories, as our democracy teeters on the brink, with Donald Trump still working overtime to push the whole thing off a cliff. On Hell and High Water, John Heilemann — host of Showtime's The Circus, co-author of Game Change, and national affairs analyst for MSNBC — explores this apocalyptic-seeming moment with seminal figures in politics, entertainment, business, tech, the media, and beyond. The conversations are deep, rich, and bracingly real, but also hopeful, as Heilemann and his guests grapple with the fact that, to quote Bob Dylan, “Everything is broken,” and try to figure out how to fix it … together.


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In which John Heilemann talks with Cecile Richards, co-chair of the Democratic super PAC American Bridge 21st Century, co-founder of the women’s rights advocacy group Supermajority, and, from 2006 to 2018, president of Planned Parenthood Federation of America. Heilemann and Richards discuss Roe v Wade's uncertain future in the wake of the recent Supreme Court arguments around restrictive abortion laws in Mississippi and Texas, and the effects that Roe's potential demise might have on women and politics in America; how Richards's mother, Ann, the former governor of Texas, propelled her towards a lifetime of activism; and how her broader agenda in favor of "women's equity" is faring in the Biden era.
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Cecile Richards

A special two-part episode in which John Heilemann talks with international affairs and national security guru Tom Nichols, contributing writer at The Atlantic, longtime senior faculty member at the U.S. Naval War College, and author of eight books on foreign policy and politics, including, most recently, Our Own Worst Enemy: The Assault from Within on Modern Democracy. Heilemann and Nichols assess the state of the Russian invasion of Ukraine, Vladimir Putin’s calculations in the face of the Russian military's inability to win a swift and decisive victory, and the emerging consensus in the West that war has reached what could prove to be a protracted and bloody stalemate; how President Zelenskyy has wielded a masterful media strategy to galvanize support around the world and dominate the information battlefield; and the difficult decisions facing Joe Biden and the NATO alliance as Zelenskyy warns that we may already have entered World War III. Nichols also discusses his proud status as a five-time, undefeated Jeopardy champion, and his well-known – and well-deserved – reputation for having indefensibly and inexplicably bad taste in music.
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Tom Nichols Part 2

Tom Nichols Part 1

Shannon Watts is the founder of Moms Demand Action For Gun Sense in America — a self-described “accidental activist” who, in less than a decade, went from being a stay-at-home mother in Indiana to the face of a national grassroots movement with more active members than the National Rifle Association. When Watts launched her advocacy group as a simple Facebook page in the wake of the Sandy Hook school shooting in December 2012, she had just 75 friends on the site but grand ambitions, boundless energy, and infinite chutzpah. Today, Moms Demand Action is part of Everytown For Gun Safety and a political juggernaut, deploying tens of thousands of volunteers and tens of millions of dollars to support candidates, legislative campaigns, and corporate reform efforts. Heilemann and Watts discuss the ways her group has changed the game on gun control, the role of women and young people in the movement, the crisis at the NRA, and why Watts believes the Biden administration will be “the strongest gun safety administration in history.”


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Shannon Watts

Kurt Andersen and Lawrence O’Donnell first met 46 years ago as undergraduates at Harvard, forming a friendship that’s flourished alongside their careers as two of their generation’s most incisive, insightful observers of American politics and culture. Andersen made his mark in the 1980s as co-founder of the iconic Spy magazine, then went on to serve as editor-in-chief of New York magazine, host of the Peabody Award-winning radio program “Studio 360,” and best-selling novelist and non-fiction author. O’Donnell cut his teeth in Washington as staff director of the powerful Senate Finance Committee and protege to legendary New York Senator Daniel Patrick Moynihan, then transitioned to the TV business — first as an Emmy Award-winning writer on “The West Wing” and currently as host of “The Last Word” on MSNBC. On this week’s Hell & High Water, Heilemann, a friend of both Andersen and O’Donnell, brings the two men together for their first-ever joint interview. They discuss the performances of Joe Biden and Amanda Gorman on inauguration day, O’Donnell’s insider’s perspective on the January 6 assault on the US Capitol, and Andersen’s “grand unified theory” of modern American life, as sketched out in his recent companion volumes, “Fantasyland” and “Evil Geniuses.”
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Claire McCaskill

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