Transcripts (12)

Andrew Ross Sorkin

Hell & High Water with John Heilemann

  • about 2 months ago
  • 01:13:13

Andrew Ross Sorkin is arguably the country's most important and influential financial and business journalist — and, without doubt, its most plugged in. Having started his career at the New York Times as intern when he was still in high school, he now presides over DealBook, which began its life in 2001 as a newsletter about Wall Street and the mergers and acquisitions game, but over the past 20 years has grown into a sprawling finance, business, and economic news fiefdom within the larger Times empire. At the same time, Sorkin is a co-anchor of Squawk Box, the daily CNBC morning show avidly watched by titans of industry and hopped-up day traders alike. He is also the author of "Too Big To Fail," the definitive chronicle of the 2007-2008 financial crisis, which was adapted into a star-studded movie of the same name by HBO; a co-creator of the hit Showtime series "Billions"; and is currently developing another film for HBO on the GameStop/Robinhood meme-stock saga. On this episode of Hell & High Water, Heilemann and Sorkin discuss how big business sees the new political era dawning in Washington, DC: from President Biden's $1.9 trillion COVID relief and economic recovery legislation to the possibility of raising the minimum wage to the deep polarization that continues to hobble American politics in the wake (and still under the influence) of Donald Trump. They also dive into the many speculative manias currently gripping the financial markets, whether this latest Big Casino moment presages a long-predicted crash, and what if anything regulators might do about the stunning power being amassed by Big Tech. Finally, Heilemann asks Sorkin to list his top five Wall Street films, and the two men riff on the unique place that the financial masters of the universe occupy in popular culture — as objects of fascination, fetishism, reverence, and revulsion in roughly equal measure. Learn more about your ad-choices at

Daveed Diggs, Ethan Hawke, and James McBride

Hell & High Water with John Heilemann

  • about 2 months ago
  • 01:12:49

The story of John Brown and Harpers Ferry is a pivotal piece of American history that's neither well-known nor well-understood — to the extent it's known or understood at all. In 1859, Brown, a militant white abolitionist and religious zealot, led a raid on the federal armory in that small Virginia (now West Virginia) town to acquire weapons and spark a slave revolt to end the peculiar institution and cleanse America of its original sin. The raid was a debacle, failing utterly in its immediate objectives, but ultimately helped to set in motion the chain of events that led to the Civil War. In 2013, the writer and musician James McBride published a novel, "The Good Lord Bird," that was a heavily fictionalized but also historically rooted account of Brown's life. The book went on to win the National Book Award for Fiction that year, and, last fall, spawned a seven-part Showtime mini-series, produced by Blumhouse Television, starring and co-created by the celebrated actor Ethan Hawke as Brown (a performance for which Hawke has been nominated for a Golden Globe this year) and Grammy and Tony Award-winning "Hamilton" phenom Daveed Diggs as the Black abolitionist icon Frederick Douglass. The TV incarnation of "The Good Lord Bird" is an incendiary, irreverent, at times hilarious, at times moving entertainment — beautifully written, gorgeously shot, studded with standout performances. But it's also something more than a stellar costume drama. In its treatment of racism not as an individual moral failing but a system of oppression; its examination of white guilt, ally-ship, and redemption; its illustration of the arguments between incrementalism and radicalism; and its forcing of the question of nonviolence versus by-all-means-necessary-ism, "The Good Lord Bird" is, as Matt Zoller Seitz put it in his review for Vulture, “a historical epic of real vision ... [that] speaks to the present as well as the past ... lead[ing] us to connect what happened back then with what’s happening on American streets right now.” As Black History Month comes to a close, Heilemann sits down with Diggs, Hawke, and McBride to discuss the series, their collaboration, and what Hawke has called the "dangerous" territory where art and race intersect — and that "The Good Lord Bird" illuminates so incandescently. Learn more about your ad-choices at

Jaime Harrison

Hell & High Water with John Heilemann

  • 2 months ago
  • 01:10:08

Jaime Harrison is one of the brightest young rising stars in the Democratic Party. Born and raised by a single mother in Orangeburg, South Carolina, educated at Yale and Georgetown Law, and mentored by legendary Palmetto State congressman Jim Clyburn, Harrison became the first African American chairman of his home state's Democratic Party in 2013, at the age of 37. After a stint as an Associate Chair of the Democratic National Committee, Harrison launched a campaign to topple incumbent South Carolina Republican Senator Lindsey Graham — a bid widely seen as a distant longshot at the outset, but that ultimately turned into one of the marquee races of the 2020 election cycle, with Harrison shattering all South Carolina fund-raising records with a $133 million haul. In the end, Graham beat back the upstart challenge, but Harrison's emergence as a national figure left no one surprised when President Biden chose him in January to be the new chairman of the DNC. In a conversation recorded as the Senate was rendering its verdict in Trump's historic second impeachment trial, Heilemann and Harrison delve into the short and long-term implications of Trump's acquittal for Republicans and Democrats alike, the existential questions it raises about our constitutional republic, and the inescapable racial dynamics at play in the terrible events of January 6. They discuss Harrison's youthful infatuation with politics, his quasi-filial relationship with Clyburn, and his ambitious plans for the DNC — from grassroots organizing to combating voter suppression to crafting a true 50-state strategy — as the national party gears up for the 2022 midterm elections and beyond. Learn more about your ad-choices at

Joyce White Vance and Jill Wine-Banks

Hell & High Water with John Heilemann

  • 2 months ago
  • 01:21:56

Joyce White Vance and Jill Wine-Banks entered the Trump era with gold-plated resumes and sterling reputations in the legal world but modest public profiles outside it. Today, however, they are widely known as two members of a cadre of MSNBC legal analysts who conducted a four-year national civics lesson about the rule of law when it was being tested in unprecedented ways — a cadre notably dominated by women, many of them pioneers in their profession. Wine-Banks earned that status in the 1970s, when, after serving as one of the first female attorneys in the Department of Justice's organized crime section, she joined the staff of Watergate special prosecutor Leon Jaworski; she later became the first female General Counsel of the U.S. Army and first female executive director of the American Bar Association. Vance, too, is a trailblazer: the first woman appointed U.S. Attorney (for the Northern District of Alabama) by President Obama, she established for the first time a civil-rights enforcement unit in that office, prosecuted numerous high-profile public corruption cases, and launched a statewide investigation into inhumane conditions in Alabama's prisons. Along with two other female legal analysts. Vance and Wine-Banks recently launched a new podcast, #SistersInLaw. And with Trump's second impeachment trial commencing this week, Heilemann invites his friends and colleagues to discuss the case against Trump and why it matters so much — even if Trump, as most expect, is ultimately acquitted. They also delve into the wave of defamation lawsuits and legal threats aimed at right-wing media companies and the former president's lawyers, the degree of legal peril facing Trump as a private citizen, and the challenges facing Attorney General nominee Merrick Garland in repairing the damage wrought by Trump at the Justice Department. Learn more about your ad-choices at

Sean Penn

Hell & High Water with John Heilemann

  • 3 months ago
  • 01:04:19

If you looked up the hyphenate "artist-activist" in an illustrated dictionary, next to the entry would likely be a picture of Sean Penn. In a film career spanning forty years, Penn has appeared in more than 50 features, received five Best Actor Oscar nominations and won the award twice — for his leading roles in "Mystic River" and "Milk" — and staked a plausible claim to being the preeminent actor of his generation. He has directed five films, three of which he wrote, as well as publishing two novels. At the same time, Penn has courted political controversy with high-profile trips to Iraq, Iran, and Cuba, and in particular with his friendship with former Venezuelan president Hugo Chavez.   But alongside his controversial forays on the world stage, much of Penn's time and energy in the past decade has been devoted to humanitarian relief efforts. In 2010, he founded a non-profit now known as CORE (Community Organized Relief Effort) to mobilize emergency workers and distribute aid in Haiti after a devastating earthquake rocked Port-au-Prince that January. CORE did the same in Puerto Rico after Hurricane Maria, in the Bahamas after Hurricane Dorian, and in Florida after Hurricane Michael. When COVID struck, CORE responded by opening 49 testing sites in the US, including the largest in the country at Dodger Stadium in Los Angeles. That facility has now been converted into a massive Covid vaccination center — without a dollar from the federal government. On this week’s episode of Hell & High Water, Heilemann brings Penn on to discuss the fight against COVID, Penn’s activism and acting career, and the lasting cultural significance of Jeff Spicoli, his character in "Fast Times At Ridgemont High." To learn more about CORE or make a donation to support their work, please visit Learn more about your ad-choices at