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The latest episode of “Sheepdog and Shepherd” features a deeply personal conversation with Ray Hassett, a retired lieutenant with the New Haven Police Department whose career has blended professional acting, undercover work, hostage negotiation, and a faith-driven approach to policing. His testimony about discernment, humanity, and the discipline required to serve others well in moments of chaos offers powerful insights.
Hassett tells hosts Kyle Reyes and Von Kliem that law enforcement was his second career, following years as a professional actor. What initially seemed like an unusual transition became a defining strength.
“When you think about it, when you’re as a young man training as an actor, you play all these complex parts… which involve emotions that you would never have if you just stayed in your lane,” Hassett explained. He said that emotional range prepared him to meet people at the worst moments of their lives.
He entered the police force in 1987 at the height of the crack epidemic in New Haven, describing unrelenting violence and dysfunction.
“You’re dealing with broken people,” he said. “And if you before you figure out how you’re going to problem solve, if you have an understanding of what those emotions feel like and how they can alter the way that you respond, I think I was ahead of the game.”
Over time, Hassett became known less for force and more for presence. He recalled earning multiple street nicknames, with the final one meaning the most to him.
“By the end of my career… people called me the crazy whisperer,” he said. “Because the more I got involved in this chaos, the more I realized that it’s not what you say, but it’s who you are.”
As an FBI-trained hostage negotiator, Hassett emphasized that people are driven by “emotion, history, and trauma.” He described running one of the busiest districts in New Haven from his patrol car, building trust by showing up consistently. “I dragged a lot of people off porches, but at the same time, I sat on a lot of porches,” he said.
That approach extended to encounters with individuals suffering from mental illness. Hassett criticized systems that offer brief evaluations without real care, but stressed the importance of follow-up. “When they come out of the hospital and they walk past your car, do you speak to them?” he asked. “What did we get out of that? The rapport between me and them for the next time.”
Hassett also discussed his time working deep undercover in organized crime, living for two years under a false identity with no backup. “If we find out you’re a cop, we’re going to kill you,” he recalled being told. “It’s serious work… and when you finish that work, you have a legacy. It’s also an adventure into PTSD.”
Faith provided stability in those dark seasons. “When you’re by yourself, when things are dark, you have to have something that is stable,” Hassett said. “The overall faith piece is leaving people better than you found them, and that’s not about me.”
Hassett’s story stands as a reminder that policing is not just about enforcement, but about faith lived out under pressure.
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