Shirley Cavanaugh

Shirley Cavanaugh

Author: Old Pros January 3, 2026 Duration: 37:08

Shirley Cavanaugh, a down on her luck sex worker, blew the lid off a corrupt police department in Pittsburgh in the 1950s. By chance she was falsely accused of shooting a cop, but instead of backing down, she fought back. What happened to her triggered a major investigation that ended in the disbandment of the Pittsburgh Vice Squad. In this episode, Kaytlin Bailey explores Shirley's story, her entanglement with an Officer and the remarkable coalition that rallied around her. Featuring interviews with Shirley's grandson Jason Kirin and Pittsburgh columnist Jessie Sage, this is a forgotten story of bravery, abuse, and resistance.

You can buy Jason Kirin's book From the Furnace With Love; The Multigenerational Tapestry of Shirley Cavanaugh, documenting his grandmother's incredible story.

Read Jessie Sage's article about Shirley Cavanaugh.

We'd like to thank our Season sponsors M e g a P e r s o n a l s, Assembly Four, Tryst, A Great Idea, and the New Moon Network.

The Oldest Profession Podcast is produced by Old Pros, a non-profit media organization that uses storytelling to advocate for sex worker rights. If you value our mission, please consider making a tax deductible donation. To learn more visit us at oldprosonline.org, which is also where you can get Old Pros t-shirts, sweatshirts, totes, stickers, and more. Of course, proceeds from our shop support our work at Old Pros.


History is often told through the lens of the powerful, but what about those who operated in the shadows? The Oldest Profession Podcast turns the spotlight on the figures who shaped culture from the margins. Hosted by Kaytlin Bailey-a stand-up comic, advocate, and self-described notorious old pro-this series digs into the lives of specific sex workers from the past, placing them firmly within the context of their era. You’ll hear about courtesans who influenced politics, brothel owners who built empires, and street-based workers who fought back against oppression, all while drawing clear lines to the modern movement for rights and dignity. It’s a blend of rigorous historical research and the kind of candid, often humorous perspective that only someone with Bailey’s unique background can provide. Created in partnership with the team at Old Pros, this podcast doesn't just recount anecdotes; it argues that understanding these "old pros" is essential to understanding our collective story. The tone is engaging and accessible, merging the depth of a history lesson with the relatable punch of comedy. For anyone curious about the untold chapters of social history, this show offers a compelling, humanizing, and surprisingly funny journey.
Author: Language: English Episodes: 100

The Oldest Profession Podcast
Podcast Episodes
The Infamous Madams of Water Street in Portsmouth, NH [not-audio_url] [/not-audio_url]

Duration: 28:49
The infamous madams of Water Street in Portsmouth, New Hampshire, were dear friends and colleagues. Mary Amazeen Baker (1859-1930) and Alta Warren Roberts (1855-1940) operated houses near each other and were well-known f…
Lulu White: Storyville's "Diamond Queen of the Demi–Monde" [not-audio_url] [/not-audio_url]

Duration: 35:40
Known as the "Diamond Queen of the Demi–Monde," Lulu White was one of the most notorious and financially successful madams of the Storyville red-light district of New Orleans. Much of Lulu White's early life remains a my…
Madam Fan Jones of Bangor, Maine [not-audio_url] [/not-audio_url]

Duration: 25:04
In 1867, Madam Fan Jones bought the Sky Blue House of Pleasure just outside of Bangor, Maine's red-light district called "The Devil's Half Acre." The Sky Blue House of Pleasure was the most popular and longest running br…
We Organized! OPN Black Sex Worker's Roundtable [not-audio_url] [/not-audio_url]

Duration: 53:58
On this special episode, host and human rights activist Lakeesha Harris gathers a legendary roundtable of leaders in the Black Sex Worker movement: performer/activists Sinnamon Love and Jet Setting Jasmine of the BIPOC A…
Who was Jezebel? [not-audio_url] [/not-audio_url]

Duration: 54:07
Old Pros Historian, Dr. Charlene J. Fletcher, and podcast host, Kaytlin Bailey, discuss who was Jezebel? How did her legacy become synonymous with morally depraved, wicked, women? Was she an old pro? Who ruined her reput…
The Everleigh Sisters' Best Brothel in Chicago [not-audio_url] [/not-audio_url]

Duration: 52:15
On February 1, 1900, the Everleigh Sisters (Minna and Ada) opened what would become the best brothel in Chicago, and for a time, the world. The Everleigh Sisters successfully ran their establishment for eleven years, fre…
Stella Darby: Beloved Madam of Pendelton, Oregon [not-audio_url] [/not-audio_url]

Duration: 29:18
Stella Darby, beloved madam of Pendelton, Oregon, was said to be a benevolent person, always giving food and clothing to those in need and encouraging her employees to pursue an education, save money, and to strive for m…
Taxation Without Representation - with Tamika Spellman [not-audio_url] [/not-audio_url]

Duration: 44:00
This week, on Old Pro News, we'll tell you about two new online reporting programs, only one of which we believe will actually keep sex workers safe. Then, we'll be chatting with Tamika Spellman, the Advocacy Manager of…