The Back Room with Andy Ostroy

Andrew Weissmann is the co-host of the popular podcast Prosecuting Donald Trump and is a frequent legal analyst for NBC/MSNBC. He serves on the board of Just Security and writes frequently for it, as well as The New York Times, The Atlantic, & The Washington Post. From 2017-2019 Andrew served as a lead prosecutor in Robert S. Mueller’s Special Counsel’s Office. His memoir about the Special Counsel investigation, Where Law Ends: Inside the Mueller Investigation , was a New York Times bestseller. He is also a Professor of Practice at New York University and teaches courses in national security and criminal procedure. He also served as the General Counsel for the Federal Bureau of Investigation and from 2002-2005 he served as the Deputy and then the Director of the Enron Task Force where he supervised the prosecution of more than 30 individuals in connection with the company’s collapse. And he was also a federal prosecutor for 15 years in the Eastern District of New York, where he served as the Chief of the Criminal Division and prosecuted numerous members of the Colombo, Gambino, and Genovese families, including the bosses of the Colombo and Genovese families. Join us for this super-insightful chat about the current status of the mounting lawsuits filed against 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

Liza Treyger is an actress, comedian, and podcaster. She’s been named one of Variety’s “Top Ten Comics to Watch,” Rolling Stone’s “Ten Comics to Watch,” and Comedy Central’s “Comics to Watch”, and her first ever hour-long comedy special entitled “Night Owl” just dropped on Netflix. She recently wrapped production on season two of Netflix’s critically acclaimed comedy series “Survival of the Thickest”, and can next be seen in the independent feature “Damned If You Do”. She’s also the co-host of the podcast, That’s Messed Up: an SVU Podcast. Jojn me for this super-fun chat with this super-funny comedian! We discuss her Netflix Comedy Special, doing stand-up in the age of 'woke', her love of Soul Cycle and weed, 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

Michael Ian Black is an actor, writer, and comedian who began his career with the legendary sketch comedy troupe, The State. He then went on to co-create several television shows, including Viva Variety, Stella, and Michael & Michael Have Issues. His other tv credits include Ed, Another Period, The Jim Gaffigan Show, and the Wet Hot American Summer franchise. His film credits include This is 40, Sextuplets, The Baxter, and Linoleum. Michael’s written several screenplays, including Wedding Daze, which he directed, and Run, Fat Boy, Run. He’s also authored many books including My Custom Van (and 50 Mind-Blowing Essays That Will Blow Your Mind All Over Your Face), You’re Not Doing It Right, and his most recent A Better Man: A (Mostly Serious) Letter to My Son. He is also the author of several award-winning books for children, including A Pig Parade Is A Terrible Idea, Chicken Cheeks, the I’m… series, and his satirical book, A Child’s First Book of Trump. Additionally, he’s hosted game shows including Trust Me I’m A Game Show Host, and Duck Quacks Don’t Echo on NatGeo. He’s co-created and hosted the How To Be Amazing, Topics, and Mike and Tom Eat Snacks podcasts and currently hosts the Obscure podcast. He’s currently a team captain on CNN’s Have I Got News For You. And he’s a stand-up comedian who has released several albums and specials and regularly tours the US. Michael and I had an insightful, fun chat about his childhood, his early comedy inspirations and career, Trump 2.0, the CNN hit show "Have I Got News For You" and more. And don't miss our riveting discussion where we debate the pecking order of dinner theater, community theater, Medieval Times and  Renaissance Fair! 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

Lindsey Boylan has spent her career in urban planning and public service. She is the former Deputy Secretary for Economic Development and Housing for New York and served as Special Advisor to former Governor Andrew Cuomo. She was the first woman to come forward with accusations about Cuomo’s abuse of women and his related abuses of power. An unapologetic feminist, her words have appeared in leading publications including Vanity Fair, Harper’s Bazaar, Teen Vogue, Rolling Stone, The New Yorker, and Gothamist. Lindsey joins me in The Back Room to share her personal story and her mission to help victims of sexual harassment. 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

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. Sabrina 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. She 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. Don't miss this super-insightful chat as Sabrina unpacks the Trump Administration 'SignalGate' national security fiasco. 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

Amanda Litman is the co-founder and President of Run for Something, a national organization that recruits and supports young, diverse progressives running for local office. She's also the author of the book, “Run for Something: A Real Talk Guide to Fixing the System Yourself,” and previously hosted two podcasts, “Run for Something: The Podcast” and “Battleground”. She’s written for Elle, Cosmopolitan, The Nation, Teen Vogue, CNN.com, MTV.com, Buzzfeed, Vanity Fair, O Magazine, Crooked Media, and others. Before launching Run for Something, she was the email director for Hillary Clinton’s 2016 presidential campaign, digital director for Charlie Crist's 2014 Florida gubernatorial campaign, and an email writer for Barack Obama’s 2012 re-election campaign. Her new book, When We're In Charge: The Next Generation’s Guide to Leadership, is on sale May 13th and available now for pre-order. I love this conversation because it helps folks at home understand how they can become a candidate for elected office and have a meaningful say in how government operates. It's an awesome call-to-action chat which stresses the critical need right now of staying positive, staying engaged, and running for something! 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

Jocelyn Benson is Michigan's 43rd Secretary of State and is running to be the next governor of the state in its 2026 election. 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 she 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 book “State Secretaries of State: Guardians of the Democratic Process”, and is a frequent tv news commentator. Her new book,“The Purposeful Warrior: Standing Up for What's Right When the Stakes Are High”, is on sale May 6th and is available for pre-order. Jocelyn and I discuss her consequential role as Secretary of State in protecting and expanding voters' rights; how she's taken on Trump; continues to defend the Constitution and the rule of law; her decision to run for governor in 2026; and her inspiring new book which provides "a road map for shattering the status quo and standing up for ourselves, our communities, and our country." 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

Jim Acosta is an award-winning broadcast journalist, with 25 years of experience in network television news, at CNN and CBS News. Perhaps best-known for his time as the Chief White House Correspondent for CNN, he has covered six straight presidential elections at the network level. He’s also as an anchor and reporter covering some of the biggest news stories of the last 30 years, including Hurricane Katrina, the Iraq War and the aftermath of 9/11. In 2019, his New York Times bestselling book, “The Enemy of the People: A Dangerous Time to Tell the Truth in America” was published. That same year his work was recognized by the New York Press Club with its “Truth to Power” Award. Jim hosts a podcast on Substack, YouTube and Apple Podcasts. Jim shares his keen insights on a variety if subjects including Trump 2.0, Musk and DOGE, the challenging road ahead for Democrats, and the administration's attacks on the media. 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

Kara Swisher is the host of the podcast On with Kara Swisher, and the co host of the Pivot podcast with Scott Galloway. Both are distributed by New York Magazine. Kara co-founded and was the editor-at-large of Recode, host of the Recode Decode podcast, and co-executive producer of the Code Conference. She was a former contributing opinion writer for the New York Times and host of its Sway podcast. She has also worked for the Wall Street Journal and the Washington Post. Burn Book is her third book and the paperback edition is now available with a brand-new afterward. Kara shares her inimitable with and wisdom on Trump, Musk, the tech broligarchy, Chuck Schumer and the rift within the Democratic Party over the GOP spending bill vote. 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

Brooke Harrington is Professor of Economic Sociology at Dartmouth College. Her most recent book, Offshore: Stealth Wealth and the New Colonialism, which the Financial Times named one of the Best Books of 2024, and the New Yorker highlighted it among the “Political Books That Help Us Make Sense of 2024.” Harrington’s previous book on offshore finance—Capital without Borders: Wealth Managers and the One Percent --won an “Outstanding Book Award” from the American Sociological Association. She is a frequent op-ed contributor to the New York Times and the Washington Post, as well as to The Guardian and The Atlantic. Brooke and I discuss Trump 2.0, Putin/Russia, the Musk-led broligarchy, and its impact on America at home and abroad. 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