The Back Room with Andy Ostroy

Latest Episodes:

Cait Conley on her NY-17 House Campaign Against Trumper Mike Lawler Oct 03, 2026

Show notes

Cait Conley is a fourth-generation Hudson Valley native and the daughter of a postal worker and a construction worker. She applied to West Point the day after 9/11 and went on to serve in the Army, first as a military police officer and then in special operations leadership, deploying six times and earning three Bronze Stars. She concluded her active-duty career as Director for Counterterrorism at the National Security Council, and then served as a senior executive at the Cybersecurity and Infrastructure Security Agency.

Cait's back in The Back Room for an update on her campaign for the U.S. House of Representatives in NY’s 17th Congressional district, a critical battle against incumbent Republican Mike Lawler.

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

Nikki Fried on Florida's Key Midterm Races and Democrats' Chances of Winning the House and Senate Oct 01, 2026

Show notes

Nikki Fried is the Chair of the Florida Democratic Party. She served as Florida’s 12th Commissioner of Agriculture and Consumer Services from 2019-2023. She is a lifelong Floridian, attorney and activist.

Nikki and I discuss her state's key House, Senate and governor's races as well as the midterms overall and Democrats' chances of winning both the House and Senate.

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

Marc Levin on his Terrific New Documentary DAUGHTERS OF 9/11 Sep 29, 2026

Show notes

Marc Levin is an award-winning, independent filmmaker. He has made over 50 films, including documentaries, TV series, dramatic feature films and episodic television. He’s won four Emmys and four duPont-Columbia Awards, among other prominent accolades. Highlights include his dramatic hit SLAM; the groundbreaking docuseries Brick City; several films for HBO including Gang War: Bangin’ in Little Rock, Thug Life in DC; Class Divide and An American Bombing; and last year’s HARD HAT RIOT on PBS.

Marc joins me to discuss his terrific new film DAUGHTERS OF 9/11, which premiered on CBS on the 25th anniversary of 9/11, and is now streaming on Paramount +. The film follows the gut-wrenching journey of two women, whose fathers were murdered that day, as they seek justice for the families while the government has yet to prosecute the mastermind of the attacks, Khalid Sheikh Mohammed, who remains in custody at Guantanamo.

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

Rick Wilson on Trump, the Midterms, and If a Blue Tidal Wave is Coming Sep 26, 2026

Show notes

Rick Wilson is co-founder and board member of The Lincoln Project. He’s 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 outlets. He’s a 30-year veteran of national Republican politics who got his start in the 1988 Presidential campaign of George Herbert Walker Bush, and has produced groundbreaking and award-winning political advertising and 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.

Are Donald Trump and the Republican Party imploding? Are we finally at the long-awaited inflection point? Is a blue tidal wave coming? Do Democrats finally have the right candidates and messaging? Are they going to win back the House AND Senate? Will Trump "run" again in '28? Will Don Jr. run? And if so, what will J.D. Vance, Marco Rubio and other potential candidates do? Rick addresses these critical questions and more.

But first, Andy and Matty discuss the breaking Supreme Court ruling on elections; Trump's media ban and new Iran threat; and AL Sen. Tommy Tuberville's "furry" fears, Plus, this week's Winners and Losers and Andy's rant on the ban.

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, the MAGA Meltdown, the Midterms, the Media Ban, and More Sep 24, 2026

Show notes

S.E. 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.

Is MAGA revolting? Are Congressional Republicans finally growing a pair? Is the inflection point finally here? Is Donald Trump's presidency imploding? Are Democrats winning back the working class? Is a blue tidal wave coming? Will Democrats take back the House and Senate? S.E. addresses these critical questions, as well as Trump's media ban, as we head towards November 3rd.

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

Dr. Zaldy Tan on his New Book "What to Remember When You Are Forgetting: How to Live and Thrive with Memory Loss, Alzheimer's, and Other Dementias" Sep 22, 2026

Show notes

Dr. Zaldy Tan is Professor, David Geffen School of Medicine at UCLA, and the Director of the Memory & Healthy Aging Program at Cedars-Sinai Medical Center. His aging and dementia research has been covered by The New York Times, Time, CNN, The Wall Street Journal, NPR, The Washington Post, The Chicago Tribute, Reuters, ABC News, and NBC News. He regularly speaks at major national and international conferences and is the author of Age-Proof Your Mind and his new book, WHAT TO REMEMBER WHEN YOU ARE FORGETTING: How to Live and Thrive with Memory Loss, Alzheimer's, and Other Dementias

All of us in one way or another are profoundly effected by memory disorders. It could involve an aging parent, a spouse, a sibling or other relative, a friend or even ourselves. Dr. Tan helps us better understand the warning signs, the treatments, and what we can do to make our loved ones' lives more comfortable as they navigate these cognitive difficulties.

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

Tara Setmayer Says "Please Dems Don't Blow It!": Trump, the Midterms, and the Fight to Save Democracy Sep 19, 2026

Show notes

Tara Setmayer is co-founder of the bipartisan superpac The Seneca Project. She’s a former GOP Communications Director on Capitol Hill and most recently served as a Senior Advisor for The Lincoln Project. She’s a political writer and commentator who’s appeared on MSNOW, CNN and other news outlets, The View, and Real Time with Bill Maher. Her writing has been featured on CNN.com, Bloomberg, The Daily Beast, Cosmopolitan, and NBC.com. In November 2020 she left the Republican Party after Donald Trump refused to concede the election to Joe Biden.

At the start of this terrific conversation Tara pleads, "Please Dems don't blow it!". We discuss Donald Trump's epic chaos and failures, whether the MAGA fever's starting to break, the momentum Democrats have heading towards November, and the critical importance of the midterms.

But first, The Back Room crew discusses the interest rate hike, Republican Rep. Maria Salazar's new anti-Trump immigration ad, the new NY Times poll, and the GOP's panic and desperation over the poll's devastating numbers.

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

Stephanie Grisham on Trump's Second-Term Behavior; the Midterms and Election Integrity; Natalie Harp; and More Sep 17, 2026

Show notes

Stephanie Grisham is the New York Times bestselling author of “I’ll Take Your Questions Now, What I Saw in the Trump White House.” During the Trump Administration she served as White House press secretary and director of communications for both the President and First Lady, Melania Trump. She is the only person in history who has held three senior roles at once, while representing both the east and west wings.

Stephanie shares her keen insights into Donald Trump's second-term behavior; the integrity of the midterm elections and the role of the courts; Natalie Harp; 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

Mark McKinnon on 9/11, 'Trump-a-palooza', Paxton v Talarico and Texas Politics, the Midterms, and More Sep 12, 2026

Show notes

Mark McKinnon is a political advisor, reform advocate, columnist, and television producer. He was the creator and co-host of Showtime's Emmy-nominated hit documentary series "The Circus”. He’s worked for many causes, companies, and candidates, including President George W. Bush, Senator John McCain, late Governor Ann Richards, and Bono. He was the chief media advisor for five winning presidential primary and general election campaigns. Dedicated to bipartisanship, McKinnon helped start No Labels. He’s been a regular columnist for The Daily Beast, The London Daily Telegraph, and Vanity Fair, and was a consultant to the HBO show “The Newsroom” and Netflix’s “House of Cards.”

Mark and I reflect back on 9/11 on this 25th anniversary, and the impact the horrific attacks have had on America since. We also discuss Trump's disastrous MAGA convention and his $5000 bribe; Paxton v Talarico and Texas politics overall; the midterms and whether Democrats will take the House and Senate; George W. Bush's 'silence'; and more.

But first, Andy and The Back Room crew share their own 9/11 remembrances and thoughts on 'TrumpCon', and dish up the week's winners and losers.

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

Jessica Tarlov on her New Book, Role on The Five, and if Civil Discourse is Possible in Donald Trump's America Sep 10, 2026

Show notes

Jessica Tarlov is a liberal co-host of The Five on FOX News, the most watched show in cable news. In addition to co-hosting The Five, Jessica plays an integral role in special coverage for the network and is a fixture on election nights and for breaking news. She also co-hosts the podcast Raging Moderates with NYU Professor Scott Galloway and previously worked as a Democratic pollster and researcher specializing in GenZ and Millennial trends. She holds a PhD in political science from the London School of Economics. Her debut book is I Disagree: Winning Arguments Without Losing Friends, which is on sale September 15th.

Jess and I discuss the book, her role on The Five, and whether it's still possible to engage in civil discourse in Donald Trump's America.

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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