All Episodes

September 18, 2025 56 mins

 This week, what does it mean to make a deal with the devil? Dan and Alana examine Richard Ogilvie and his tumultuous path to governor of Illinois, and whether the moral compromises he made to get there were worth the legacy (or lack of one) he leaves behind. Plus, the shocking history of mafia infiltration of queer nightlife, and how corrupt policing and homophobia continue to resound today. 


Sources:

Newspapers including The Chicago Tribune, The Chicago Sun-Times, The Chicago Reader, The Windy City Times, Arlington Heights Daily HeraldThe Daily Calumet, Columbia Journalism Review, Chicago American, Chicago Daily News.

PBS SoCal

---

The Outfit is a production of Higher Ground and Headgum.

Hosted by Dan O’Sullivan and Alana Hope Levinson

Executive Produced by Dan O’Sullivan and Alana Hope Levinson

Produced by Julia Murray

Production Assistance by CJ Archerd and Franchesca Diaz

Sound Design and Engineering by Ryan Kozlowski and Andrew Eapen

Managing Producer is Tiffany Hammond

Show theme is Bittersweet Defeat by OTE


Like the show? Rate The Outfit on Spotify and Apple Podcasts and leave a review.

Follow Headgum on TwitterInstagram, and Tiktok

Advertise on The Outfit via Gumball.fm

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Mark as Played

Advertise With Us

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Are You A Charlotte?

Are You A Charlotte?

In 1997, actress Kristin Davis’ life was forever changed when she took on the role of Charlotte York in Sex and the City. As we watched Carrie, Samantha, Miranda and Charlotte navigate relationships in NYC, the show helped push once unacceptable conversation topics out of the shadows and altered the narrative around women and sex. We all saw ourselves in them as they searched for fulfillment in life, sex and friendships. Now, Kristin Davis wants to connect with you, the fans, and share untold stories and all the behind the scenes. Together, with Kristin and special guests, what will begin with Sex and the City will evolve into talks about themes that are still so relevant today. "Are you a Charlotte?" is much more than just rewatching this beloved show, it brings the past and the present together as we talk with heart, humor and of course some optimism.

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.