Behind the Walls: Dave Grosky on Life inside with Chicago’s Jerry Scalise

·30 min·3 clips

A former lawyer reveals what life was like sharing a prison with Chicago mobster Jerry Scalise for nearly 11 years.

Host Gary Jenkins, a retired Kansas City Police intelligence detective, welcomes guest Dave Grosky, who contacted him via LinkedIn. Grosky served nearly 11 years in federal prison for white-collar crime and spent time with Chicago mobster Jerry Scalise. He began his sentence at FCI Loretto in 2008, where he kept quiet initially but later used his legal background to help other inmates. Grosky describes how mobsters in prison had access to better food and commissary connections, similar to depictions in movies like Goodfellas. He became close with Jerry Scalise at FCI Milan during his last six years, portraying Scalise as intelligent, humble, and helpful to others. Scalise taught a screenwriting course in prison and has connections to director Michael Mann. The host recounts Scalise's criminal history, including being part of the 'wild bunch' in Chicago and his famous heist with Art Rachel where they stole diamonds from a London jewelry store, including the Marlboro diamond, which was never recovered. Grosky notes that Scalise and other mob guys rarely discussed their past crimes but were respectful and kept to themselves. He contrasts New York and Chicago mob mentalities in prison, with New York guys often looking down on others. Grosky reflects on how prison gave him a broader perspective on life, exposing him to diverse people and experiences. He discusses the psychological impact of long-term incarceration and the lack of reintegration support from the federal system. Grosky now helps inmates with legal appeals and teaches courses on reintegration. The episode ends with Grosky sharing personal challenges, including battling cancer in prison and adjusting to life after release during COVID-19.

As heard by us

A prison-focused Gangland Wire episode on Jerry Scalise, inmate legal help, loyalty, and release.

Gangland Wire sets Dave Groski's prison years alongside Jerry Scalise's reputation inside, with Gary Jenkins guiding a measured conversation about federal prisons, mob circles, and the useful bonds that can form there.

Read the full review in PlayNext →

Why you'd press play

You get a conversational look at Dave Groski's time in federal prison with Jerry Scalise, plus the practical favors and warnings that can follow men back outside.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Gangland Wire