The Back Room with Andy Ostroy

Latest Episodes:

Miles Taylor on Lindsey Graham, Trump, Iran, Israel and Netanyahu, Ukraine, the Midterms, and More Jul 30, 2026

Show notes

Miles Taylor is a national security expert, NYT bestselling author, and co-founder of defiance.org. He previously served as chief of staff at the US Department of Homeland Security, where he published a bombshell “Anonymous” essay in The New York Times, blowing the whistle on presidential misconduct. He later published the #1 national bestseller A Warning, revealed himself to be the author, and launched a campaign of ex-officials to oppose Donald Trump’s reelection. He’s worked as an advisor in the George W. Bush administration, on Capitol Hill, as a CNN contributor, and is the co-founder of a DC-based charter school and multiple democracy-reform groups. He is also the author of The New York Times best-selling book Blowback and the host of the iHeartRadio podcast “The Whistleblowers”.

Miles and I discuss Lindsey Graham's legacy and funeral; Trump, the Iran war, Israel and Netanyahu; Ukraine and Russia; the Midterms 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

S.E. Cupp on Trump 2.0, Iran, Hegseth, MAGA, the Midterms and More Jul 25, 2026

Show notes

S.E. Cupp is a nationally syndicated columnist, author, podcaster and TV commentator. She hosts Off the Cupp, a podcast which focuses on mental health, and which features interviews with celebrities and newsmakers. She is a columnist at the New York Daily News and has also been published in the New York Times, Vanity Fair, Rolling Stone, Washington Post and many other publications. She is currently a political commentator at CNN. She regularly interviews authors for CSPAN's BookTV, and is a regular guest on The View, Real Time w/Bill Maher, Jimmy Kimmel Live!, Watch What Happens Live and others. SE has also consulted on Aaron Sorkin's The Newsroom and AppleTV's The Morning Show, and has made cameos on House of Cards and SNL. As an author SE has written two books, Losing Our Religion: The Liberal Media's Attack on Christianity, and co-authored Why You're Wrong About the RIght. She is on the Advisory Board of Cornell University's Institute of Politics and Global Affairs and INARA.org, and is a No Kid Hungry ambassador.

S.E.'s back, and as always it's super fun! After a little chat about the joys of coffee vs tea, we discuss the latest with Trump 2.0, the Iran War, Pete Hegseth, MAGA, the midterms 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

Joe Walsh on Trump, the Parties, MAGA, Midterms, Democracy and More Jul 23, 2026

Show notes

Joe Walsh is a former Republican Congressman from Illinois elected to Congress in the TEA Party wave of 2010. Following his service in Congress, Joe became one of the most popular syndicated conservative talk radio hosts in the country. In August of 2019 he became a candidate for President of the United States, waging a Republican primary challenge against Donald Trump. He is the author of F*CK SILENCE: Calling Trump Out for the Cultish, Moronic, Authoritarian Con Man He Is. He's currently the Director of The Social Contract and the host of “The Social Contract With Joe Walsh,” podcast. He appears regularly on CNN, MSNOW, News Nation and The BBC.

Sometimes I feel that Joe and I were separated at birth, and while he headed right and I went left, here we are 60 years later on the same side! Which is why it's always a blast when he brings his inimitable wit, wisdom and fire-in-the-belly into The Back Room to discuss Trump, the political parties, MAGA, and the future of our democracy. Don't miss this super-fun and insightful chat!

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

MI Secretary of State Jocelyn Benson on her Campaign for Governor, Election Integrity, and the Upcoming Midterms Jul 18, 2026

Show notes

Jocelyn Benson is Michigan's 43rd Secretary of State and is running for governor. She has become one of the nation’s most prominent leaders in ensuring elections are secure and accessible. Her work overseeing Michigan’s 2020 and 2022 general elections earned her national recognition, including the John F. Kennedy Profile in Courage Award and the Presidential Citizens Medal. She also implemented new voting rights for all eligible Michiganders prior to the 2020 election, including the right to vote absentee, and oversaw more than 250 audits after the election, all of which affirmed its integrity and accuracy.

At 36 Jocelyn was appointed dean of Wayne State University Law School in Detroit, becoming the youngest woman in U.S. history to lead a top-100, accredited law school, and continues to serve as vice chair of the advisory board for the Levin Center at Wayne Law, which she founded with former U.S. Sen. Carl Levin. She is the author of the books “State Secretaries of State: Guardians of the Democratic Process”, and last year’s “The Purposeful Warrior: Standing Up for What's Right When the Stakes Are High”. She is also a frequent tv news commentator. And she's back in The Back Room to discuss the campaign, election integrity, and the upcoming midterms.

But first, Matty and I discuss Trump's desperate, bizarre address to the nation last night.

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

Dan Osborn on his Independent U.S. Senate Campaign in Nebraska. And Stick Around for the Trump, Sanders and Jimmy Stewart Impressions! Jul 16, 2026

Show notes

Dan Osborn is a former union leader who gained national attention leading the 77-day Kellogg's strike in Omaha in 2021. A U.S. Navy veteran and father of three, he's spent the last 20 years punching a clock as a steamfitter and industrial mechanic. He is running for the U.S. Senate in Nebraska as an independent candidate focused on economic issues affecting working families.

Dan and I discuss the campaign and end with some pretty funny impressions of Donald Trump, Jimmy Stewart and Bernie Sanders...but you'll have to listen to find out who does who!

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

Cait Conley on her Campaign to Beat Mike Lawlor and Flip NY's 17th Congressional District Jul 14, 2026

Show notes

Cait Conley is a fourth-generation Hudson Valley native, daughter of a postal worker and a construction worker, a decorated combat veteran and national security expert. And she’s running for the House in NY’s 17th Congressional district. She recently won the Democratic Party's nomination to face-off against incumbent Republican Rep. Mike Lawlor in New York's 17th Congressional district in the November midterms.

Cait and I discuss her campaign, the broken promises and failures of Trump 2.0 and the Republican Party, and her plan to address the affordability crisis facing the working and middle classes.

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

Brian Tyler Cohen on Trump, SCOTUS, the Midterms, Democracy, Platner, Mamdani, Iran, and his Terrific New Book The Day After Jul 11, 2026

Show notes

Brian Tyler Cohen is a progressive YouTuber, podcaster, and host of the No Lie with Brian Tyler Cohen podcast. He’s built an audience of millions across platforms and billions of views on YouTube. His first book, Shameless, was a #1 New York Times bestseller. His new book, THE DAY AFTER: How to Wield Power in a Post-Trump World, goes on sale July 14th.

Brian and I discuss the book and the current threats to our democracy from Trump 2.0; his prediction for the upcoming midterm elections; expanding the Supreme Court; and his thoughts on the Graham Platner fiasco, NYC Mayor Zohran Mamdani's performance, and the Iran war horizon.

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

Emily Suttle-Braun on Dating Graham Platner and her Newsweek Op-ed About Believing his Accusers Jul 09, 2026

Show notes

Emily Suttle-Braun is the founder and CEO of Doodle Mom Strategies, a growth and sales partner for political tech companies, agencies, and data platforms. She has over 15 years of experience in campaigns, advocacy, and political tech highlighted by her work on the 2016 Hillary Clinton and 2020 Biden-Harris campaigns.

About a decade ago Emily dated embattled former Maine U.S. Senate democratic nominee Graham Platner. She joins me to discuss their time together, how he treated her, and the terrific Newsweek op-ed she just wrote about believing his accusers Jenny Racicot and Lindsey Fifield.

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

Suzanne Vega on Life, "Luka", her Recently Released Film LOVER, BELOVED, and More Jul 08, 2026

Show notes

Suzanne Vega emerged as a leading figure of the folk-music revival of the early 1980s. Since the release of her self-titled, critically acclaimed 1985 debut album, she has written and recorded numerous songs that have become part of the contemporary music vernacular, including “Luka,” “Marlene on the Wall” and “Tom’s Diner,” an a cappella piece that was remixed by U.K. electronic dance duo DNA and became a major club hit. It remains an oft-sampled and covered standard by artists across the musical spectrum. Her albums, including her self-titled debut, follow-up Solitude Standing and 99.9F have sold millions of copies worldwide. Her most recent album, 2025’s Flying With Angels, is out now on Cooking Vinyl to critical acclaim from The New York Times, Rolling Stone, New York Magazine, Forbes and more.

Suzanne and I talk about her life, music, and her recently released LOVER, BELOVED, the critically acclaimed film adaptation of her acclaimed one-woman stage show about the life of the great 20th-century American writer Carson McCullers. And she shares the heartbreaking backstory of her iconic and haunting 1987 hit "Luka", sung through the voice of an abused little boy, but which she revealed in 2021 was actually about her own childhood trauma.

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

Rina Shah on Being a "RINO" and How America Can Ultimately Have a Functioning Two-Party Political System Again Jul 04, 2026

Show notes

Rina Shah is a Washington, DC-based geopolitical risk adviser, political strategist, and frequent on-air commentator. She is the Founder of Vental Strategic Advisory Group. With experience as a Capitol Hill senior aide to two members of Congress, chief spokesperson for two presidential campaigns, and trusted counselor to CEOs, elected officials, and diplomats worldwide, she’s been a leading voice on U.S. foreign policy, national security, and center-right principles grounded in the rule of law. She is a Senior Fellow at the Rainey Center for Inclusive Governance and a Senior Advisor to Our Republican Legacy. She serves on multiple boards including the Renew Democracy Initiative, and is Co-Founder of Women’s Public Leadership Network which she started with Melinda Gates’ backing. She was named one of Business Insider’s ‘20 political strategists to watch’ for the last election cycle. And she bravely became the first #NeverTrump RNC delegate in 2016. She appears regularly on CNN, BBC, CBS, MSNOW, NewsNation, and other major news outlets.

So is the Republican Party dead or just badly broken? Rina shares her personal story of becoming a "RINO" and how we can one day have a functioning two-party political system again.

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

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