
The Back Room with Andy Ostroy
The Back Room with Andy Ostroy presents a humorous, honest take on politics and pop culture featuring notable guest interviews, a shit-ton of righteous indignation, and rip-roaring repartee with co-producers Matty Rosenberg and Jen Hammoud. We're havin' a ball, and so will you!
Got somethin' to say?! Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Music by Andrew Hollander
Design by Cricket Lengyel
Latest episodes

Jun 28, 2025 • 52min
Tracy Walder on her Incredible Journey from Sorority House to the CIA and FBI
Two weeks after graduating from USC, Tracy Walder began her career as a Staff Operations Officer in the Central Intelligence Agency's Counterterrorism Center before, during and after September 11th 2001, and as Special Agent at the FBI. During her time at the CIA, she lived in and travelled to countries in the Middle East, Africa, and Europe as well as served in war zones such as Afghanistan. After the CIA, Tracy became a Special Agent at the FBI's Los Angeles Field Office, Santa Ana Resident Agency.
Following her time at the CIA and FBI, she received her master’s in teaching at Chapman University and began teaching history and a course created for young women on national security and global policy at high schools in California and Texas. She now works as an adjunct instructor of Criminal Justice at Texas Christian University, is the national security contributor for News Nation and appeared on the Discovery Channel’s Lost Monster Files, the History Channel, and the Discovery Channel. She is currently the star of the number one documentary on Netflix American Manhunt: Osama Bin Laden.
Tracy shares her incredible story of going from sorority sister to CIA and FBI agent, and details her work in law enforcement, counter-terrorism and national security. We discuss her key role in the new Netflix doc, the rampant sexual harassment she experienced at the Bureau, and whether America is safe from domestic and foreign terrorists under the Trump administration.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 23, 2025 • 47min
George Conway on Iran and MAGA, Trump's sociopathy; the Musk Breakup; Newsom and the National Guard case; the Failed Birthday Parade; and More!
George Conway is an attorney, political activist, legal and political commentator, and a founder of The Lincoln Project. He is a host of The Bulwark’s podcast George Conway Explains It All (to Sarah Longwell), and he is a contributing writer to The Atlantic. He previously worked as a litigator for three decades at the law firm of Wachtell, Lipton, Rosen & Katz in New York City.
Few people are smarter, funnier and more outspoken than George! And he's back with us to share his wit and wisdom on Iran and its impact on MAGA; Trump's sociopathy and his assault on democracy; which Cabinet member will be fired first; the Musk breakup; Gavin Newsom and immigration, ICE and the National Guard case; tariffs and trade wars; the failed birthday parade; and the No Kings protests.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 21, 2025 • 1h 5min
Leah Litman on Trump's Legal Cases, his Humiliating Parade, the No Kings Protests, and her Scorching New Book on the Supreme Court. And, Taylor Swift Too!
Leah Litman is a professor of law at the University of Michigan and a former Supreme Court clerk. In addition to co-hosting Strict Scrutiny, she writes frequently about the Court for media outlets including The Washington Post, Slate, and The Atlantic, among others, and has appeared as a commentator on NPR and MSNBC, in addition to other venues. She has received the Ruth Bader Ginsburg award for her “scholarly excellence” from the American Constitution Society and published in top law reviews. Her new book is LAWLESS: How the Supreme Court Runs on Conservative Grievance, Fringe Theories, and Bad Vibes.
Leah and I discuss Trump's legal cases, his humiliating birthday parade, the No Kings protests, her scorching new book on the Supreme Court, the key SCOTUS rulings to come by month's end, and, she reveals her favorite musical artists, including her #1, Taylor Swift!
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 19, 2025 • 23min
Ruth Ben-Ghiat on Trump's Push Towards Autocracy and How the Resistance Can Defeat Him
Ruth Ben-Ghiat is Professor of History at New York University. She writes about fascism, authoritarianism, and propaganda. She is the recipient of Guggenheim and other fellowships; an advisor to Protect Democracy; an MSNBC opinion columnist and television commentator; and publishes Lucid, a newsletter on threats to democracy. Her latest book, Strongmen: Mussolini to the Present, looks at how illiberal leaders use propaganda, corruption, violence, and machismo - and how they can be defeated.
What's happening in Los Angeles with Trump's use of the National Guard and the Marines? What's his end goal? Are we headed towards autocracy? How effective are the No Kings protests and the resistance movement? And how can her book serve as a guide for navigating through this existential crisis? Ruth answers these questions and more. Don't miss this incredibly insightful conversation.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 16, 2025 • 23min
Rick Wilson on Trump's Incendiary LA Power Grab and his Epic Break-Up with Elon Musk.
Co-founder and Board Member of The Lincoln Project, Rick Wilson is a renowned political strategist, infamous award-winning ad-maker and podcast host, writer, speaker, and political commentator on MSNBC, CNN, ABC News, NPR, Real Time with Bill Maher, and various American and international news national outlets. A 30-year veteran of national Republican politics, Rick got his start in the 1988 Presidential campaign of George Herbert Walker Bush and has produced groundbreaking and award-winning political advertising, strategic counsel to winning political candidates, SuperPACS, state parties, the national campaign committees, and corporate, association, and government clients across the nation and around the world. Rick has authored two New York Times bestsellers – Everything Trump Touches Dies and Running Against The Devil – A Plot To Save America from Trump And Democrats From Themselves – and often writes for The Washington Post, Politico, Rolling Stone, The Hill, The Bulwark, and the London Spectator.
Rick brings back his inimitable wit and wisdom for a chat about Trump's incendiary autocratic actions in Los Angeles and his epic break-up with Elon Musk.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 14, 2025 • 41min
Jon Michaels on the Legality of Trump's Authoritarian Actions in Los Angeles
Jon Michaels is a UCLA professor of law specializing in constitutional and national security law. His award-winning scholarship has appeared in the Yale Law Journal, University of Chicago Law Review, and Harvard Law Review, and he has written popular essays for the New York Times, Washington Post, Los Angeles Times, Foreign Affairs, and Guardian. A Yale Law graduate and Supreme Court clerk, Michaels is a member of the American Law Institute and serves on the advisory board of UCLA’s Safeguarding Democracy Project. His latest book, co-written with David Noll, is VIGILANTE NATION: How State-Sponsored Terror Threatens our Democracy
Is what Donald Trump's doing in LA with the National Guard and the Marines legal? Constitutional? And what happens next? Who ultimately will win this consequential national showdown between Gov. Gavin Newsom and Trump. Jon answers these questions and more.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 9, 2025 • 36min
Jake Tapper on His New Book ORIGINAL SIN: President Biden’s Decline, Its Cover-up, and His Disastrous Choice to Run Again
Jake Tapper wrote the bestselling nonfiction book The Outpost: An Untold Story of American Valor, which was turned into a critically acclaimed film in 2020, and two New York Times bestselling novels, The Hellfire Club and The Devil May Dance. He is an Emmy Award-winning TV journalist as lead DC anchor and chief Washington correspondent for CNN. His new book, which he co-wrote with journalist Alex Thompson, ORIGINAL SIN: President Biden’s Decline, Its Cover-up, and His Disastrous Choice to Run Again.
ORIGINAL SIN is currently #1 on the NY Times bestsellers list and is the hottest, most talked about book in the country...and Jake's in THE BACK ROOM discussing it.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 7, 2025 • 47min
Rep. Jamie Raskin on the Trump/Musk Break-Up, the Big Ugly Bill, Antisemitism, and his "BiPAWtisan" Bark Act!
Congressman Jamie Raskin represents Maryland’s 8th Congressional District. He is the Ranking Member of the House Committee on Oversight and Accountability. he was the lead impeachment manager in Donald Trump’s second impeachment trial and served on the Select Committee to Investigate the January 6th Attack on the United States Capitol.
Prior to his time in Congress, he was a three-term State Senator in Maryland, and was also a professor of constitutional law at American University’s Washington College of Law for more than 25 years. He has authored several books, including the Washington Post best-seller Overruling Democracy: The Supreme Court versus the American People, the highly-acclaimed We the Students: Supreme Court Cases For and About America’s Students, and the New York Times #1 best-seller Unthinkable: Trauma, Truth and the Trials of American Democracy.
The congressman and I discuss the Trump/Musk break-up, the House's Big Ugly Bill, the rise in antisemitic rhetoric and hate crimes, and his awesome "BiPAWtisan" Bark Act, which helps animal shelters receive donations for dog and cat food, leashes, blankets and other items.
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 5, 2025 • 30min
Brian Crano and David Joseph Craig on Their Terrific, Hilarious New Film I DON'T UNDERSTAND YOU
Brian Crano & David Joseph Craig are a married writer/director duo: David began his career as a writer and performer at the Upright Citizens Brigade in New York City and has worked with director Joel Edgerton for over a decade producing and acting in features Boy Erased and The Gift. Brian’s directorial debut, A Bag Of Hammers, starred Jason Ritter and Rebecca Hall and premiered at SXSW. His feature film Permission, premiered at Tribeca Film Festival and starred Rebecca Hall, Dan Stevens and featured David who also appeared in Brian’s short Dog Food (SXSW). His short films Official Selection and Rubberheart have screened at dozens of festivals worldwide. Their new film I DON’T UNDERSTAND YOU, which stars Nick Kroll, Andrew Rannells, and Amanda Seyfried, and opens in theaters tomorrow, June 6th.
Join us for this fun chat as David and Brian discuss their childhoods, early filmmaker inspirations, work/life relationship, and their terrific, hilarious new dark comedy!
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel

Jun 3, 2025 • 30min
Alec MacGillis on Trump, DOGE, Musk and the Assault on Data
Alec MacGillis worked for six newspapers, including The Baltimore Sun and The Washington Post, before transitioning to magazines in 2011, at The New Republic before eventually joining ProPublica in 2015. His work has appeared in The New Yorker, The Atlantic and The New York Times Magazine, among others. He won the 2016 Robin Toner Prize for Excellence in Political reporting, the 2017 Polk Award for National Reporting and the 2017 Elijah Parish Lovejoy Award. He is the author of “The Cynic: The Political Education of Mitch McConnell” and “Fulfillment: America in the Shadow of Amazon.”
Alec joins me for a conversation about his recent ProPublica essay on the government’s assault on data: “Trump’s War on Measurement Means Losing Data on Drug Use, Maternal Mortality, Climate Change and More”
Got somethin' to say?!
Email us at BackroomAndy@gmail.com
Leave us a message: 845-307-7446
Twitter: @AndyOstroy
Produced by Andy Ostroy, Matty Rosenberg, and Jennifer Hammoud
@ Radio Free Rhiniecliff
Design by Cricket Lengyel