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

In this revealing episode of Gangland Wire, retired intelligence detective Gary Jenkins sits down with Dave Grosky, a man who spent over a decade inside federal prisons—and came out with a story unlike any other. From FCI Loretto to Morgantown to Milan, Dave’s journey through the prison system introduced him to a cast of characters that included notorious organized crime figures—none more compelling than Chicago mobster Jerry Scalise. Dave opens up about the realities of prison life, shattering the myth of so-called "white-collar prisons." He recalls how he started off flying under the radar, eventually becoming the go-to jailhouse lawyer who helped fellow inmates with their legal battles. His insider knowledge of the prison legal system offers rare insights into the inner workings of federal institutions and the complex struggles inmates face daily. The heart of this episode centers on Dave’s six-year friendship with Jerry Scalise, a former Chicago Outfit member and mastermind behind high-profile heists—including the infamous Graff Jewelry store robbery in London. Dave paints a surprising portrait of Scalise, describing him as intelligent, generous, and deeply respected behind bars. Despite Jerry’s criminal history, his actions inside prison—mentoring others, offering legal guidance, and preparing inmates for life after release—reveal a more nuanced, human side of the mobster. We also revisit some of Jerry’s most notorious exploits, including the legendary Marlboro Diamond heist. The fate of that diamond still remains a mystery, and Dave offers a few tongue-in-cheek theories of where it might be hiding today. Beyond the stories of crime and camaraderie, Dave speaks candidly about the psychological toll of long-term incarceration and the steep challenges of reentering society—especially in a post-pandemic world. His reflections reveal a broken system where few resources exist to support real rehabilitation, leaving many former inmates at risk of falling back into old patterns. This episode offers more than just mob tales and prison anecdotes—it’s a raw, thought-provoking look at crime, punishment, and the long road to redemption. Subscribe to get gangster stories weekly. Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire Click here to "buy me a cup of coffee" To go to the store or make a donation or rent Ballot Theft: Burglary, Murder, Coverup, click here To rent Brothers against Brothers, the documentary, click here. To rent Gangland Wire, the documentary, click here To buy my Kindle book, Leaving Vegas: The True Story of How FBI Wiretaps Ended Mob Domination of Las Vegas Casinos. Transcript [0:00] Well, hey, all you wiretappers, good to be back here in the studio of Gangland Wire. You know, this is retired Kansas City Police Detective, Intelligence Unit Detective, I should add that, Gary Jenkins. A lot of y'all already know me, and if you don't, that's who I am. And I have a man here on the Zoom call that Dave Grosky, that Dave spent time with Jerry Scalise. He got a hold of me through LinkedIn, and he said, hey, I was in the penitentiary with Jerry Scalise, and he's a good guy. And I said, yeah, I'd love to tell his story. I said, can you get him to get on my show? Well, they can't get him to get on my show because I know Jerry's out and he's somewhere. I don't know where he is. I think he's in Chicago, but I don't know. And his old rap partner, Art Rachel's out. And Dave has met both those guys and other mob guys because he was in penitentiary with several of them. So Dave, welcome. I really appreciate you responding on the LinkedIn. Well, Gary, it's a pleasure. And, uh, yeah, I mean, I, uh, I was, uh, in several federal prisons for almost 11 years. I began at FCI Loretto in 2008 and there, there were some Gambinos and a variety of mob guys. I never really got to know them there. Well, I was, you know, I was new to prison, so I was really keeping quiet.