Sabrina Singh is a veteran strategist with 15 years of experience advising national leaders on crisis communications, strategic messaging, and policy issues. In addition to frequently appearing on international and national broadcast TV and digital platforms, she’s advised senior leaders at all levels of government, including Members of the U.S. House and Senate, Governors, the Secretary of Defense, and the Vice President of the United States. Most recently, she served as the deputy press secretary at the Department of Defense. Additionally, she served as an advisor to Secretary Lloyd Austin and frequently traveled with the Secretary overseas, including to Ukraine, Japan, the Philippines and Israel. She was one the Department’s most outward facing voices on the Pentagon’s efforts to surge security assistance to Ukraine and support to Israel following the October 7th attack.

Sabrina previously served as deputy press secretary for Vice President Kamala Harris, senior spokesperson roles for Mike Bloomberg’s 2020 presidential campaign, Cory Booker’s presidential campaign and previously served in various communications roles for Democratic committees, Hillary Clinton’s 2016 presidential campaign and Members of Congress.

Join us for this compelling chat about Trump 2.0, Musk, DOGE, the challenging road ahead, and the fate of democracy.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Deborah Pearlstein is Director of the Princeton Program in Law and Public Policy and Charles and Marie Robertson Visiting Professor of Law and Public Affairs. Her research on the U.S. Constitution, international law, democracy and national security has appeared widely in leading law journals and in the popular press, including The Atlantic, Foreign Policy, the Washington Post, and the New York Times.

She serves on the editorial board of the Journal of National Security Law and Policy, and was appointed in 2021 to a U.S. State Department Advisory Committee focused on helping to ensure the timely declassification and publication of government records surrounding major events in U.S. foreign policy. Throughout her tenure, she has worked closely with members of the defense and intelligence communities, including in helping to bring together retired military leaders to address key policy challenges in U.S. counterterrorism operations. Before embarking on a career in law, she served in the White House from 1993 to 1995 as a Senior Editor and Speechwriter for President Clinton.

Deborah and I discuss her latest New York Times opinion piece, The Law Is Not Fully Trump's Yet, and whether the judicial system can and will serve as an effective check on Donald Trump's most destructive, democracy-endangering actions.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Anthony Scaramucci is the founder and managing partner of global investment firm SkyBridge. He's the author of five books, including last year’s From Wall Street to the White House and Back, and his new book The Little Book of Bitcoin: What You Need to Know that Wall Street Has Already Figured Out (Feb 11). He also hosts the Open Book podcast and co-hosts The Rest is Politics: US podcast. And he’s of course well-known for the 11 roller coaster days he served in the first Trump White House as Communications Director, after having served on Trump's Finance Committee and then on his Presidential Transition Team.

Mooch opines, as only Mooch can, on Trump 2.0, the GOP, Democrats and the challenging road ahead!

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Norman Ornstein is an author, political scientist and emeritus scholar at the American Enterprise Institute. He’s is a contributing editor and writer for The Atlantic and has been an election eve analyst for CBS News and BBC News. He was named one of the top 100 global thinkers in 2012 by Foreign Policy Magazine and one of the 250 most influential people in Washington in 2021 by Washingtonian Magazine, and in every year since. His many books include The New York Times bestseller, It's Even Worse Than It Looks with Tom Mann, and the NYT and WAPO best-seller One Nation After Trump: A Guide for the Perplexed, the Disillusioned, the Desperate and the Not-Yet-Deported with EJ Dionne and Tom Mann.

Join Norm and I as we discuss Trump 2.0 and the challenging road ahead, as well as our shared experience with tragedy, loss and grief. It's an in-depth chat you don't wanna miss...

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Rosanna Arquette is an award-winning actor, film director, producer and activist. Her film credits include SOB, THE EXECUTIONER’S SONG, DESPERATELY SEEKING SUSAN, AFTER HOURS, PULP FICTION, CRASH, NOWHERE TO RUN, NEW YORK STORIES and THE BILLIONAIRE BOY’S CLUB. She’s done a ton of television over the years, including WHAT ABOUT BRIAN, THE L WORD, RAY DONOVAN and most recently the terrific PRESUMED INNOCENT, which is streaming on APPLE TV.

I've known Ro for almost 20 years now, and so it was a real honor to have her join me for this fun, insightful, poignant chat about life, love, loss, work and politics.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Congressman Pat Ryan represents Upstate New York's 18th Congressional District. He's a West Point graduate, former Army Captain, and Ulster County Executive. He served two tours in Iraq where he led soldiers of all backgrounds in combat and earned two Bronze Stars.

Join us for this important chat about the current political landscape under Trump 2.0 and what Democrats can and should do going forward to win the 2026 midterms and the next presidential election in 2028.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Ron Filipkowski is a former US Marine, State prosecutor, federal prosecutor, police academy director, lifelong Republican, Republican Club President, and was appointed by Rick Scott and Ron DeSantis to the Judicial nominating committee. Ron was a Republican Against Trump in 2020 and switched parties Jan 7, 2021. He left private-practice a year ago to become Editor in Chief of Meidas Touch. And he is co-host of the podcast Uncovered ,which focuses on covering the MAGA movement.

Ron's a smart, funny, no-bullshit guy. Join us as we get into the November election, Trump 2.0, and the challenging road ahead.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

R.J. Cutler is an award-winning director and producer who has been making documentary film and television series for over thirty years. Cutler’s work has been nominated for an Academy Award, and he is the recipient of numerous other awards including three Emmys, two Peabody Awards, and a GLAAD Award. In 2009, the Museum of Television and Radio held a four-day retrospective of R.J.’s work. In 2021, he was the recipient of the Critic’s Choice Awards Pennebaker Award for Lifetime Achievement in Documentary Film. In 2020, Cutler launched This Machine, a production company focused on developing and producing documentary projects for film and television, which is now a part of Sony Pictures Television.

R.J.’s film’s include THE WAR ROOM, BELUSHI, BILLIE EILISH: THE WORLD’S A LITTLE BLURRY, MARTHA and ELTON JOHN: NEVER TOO LATE. His television work includes Freshman Diaries, 30 Days, Elton John Live: Farewell from Dodger Stadium, Murf the Surf, Big Vape, Nashville, If I Stay, and The Oval Office Tapes.

Join me for a fun, fascinating chat with R.J. about his early life and inspirations and his stellar career as a producer and director.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Christopher Cox is a Senior Scholar in Residence at the University of California, Irvine, a Life Trustee of the University of Southern California, Chair of the Rhodes Scholarship selection committee for Southern California and the Pacific, and a member of several nonprofit and for-profit boards. Between two decades as a practicing lawyer, he served as chair of the Homeland Security Committee in the US House of Representatives, chair of the US Securities and Exchange Commission, and senior associate counsel to the President. He has written for Fortune, The Wall Street Journal, The New York Times, Forbes, The Detroit News, The Denver Post, The Washington Post, the Los Angeles Times, and dozens of other publications. His new book is Woodrow Wilson: The Light Withdrawn.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud

Juanita Tolliver is an MSNBC Political Analyst, an Opinion Contributor for theGrio, and a Contributor for SiriusXM Progress. Previously, she served as the Director of Campaigns at the Center for American Progress. She is a graduate of the Fletcher School of Law and Diplomacy at Tufts University, and the University of North Carolina at Chapel Hill. Her new book, A More Perfect Party: The Night Shirley Chisholm and Diahann Carroll Reshaped Politics, is on sale January 14th.

Join us as Juanita takes us in riveting detail through the fascinating life and historic career of Shirley Chisholm.

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Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud