Matt Frey spent seven years working as a therapist inside Rikers Island from 2011 to 2018, a job he never imagined taking growing up in the suburbs of New York. In this episode, Matt gives a rare inside look at day-to-day life at Rikers from the inmate perspective, breaking down what really happens in both General Population and Mental Observation housing. He shares firsthand experiences with extreme violence, inmate suicides, unprovoked attacks on staff, and the psychological toll of working inside one of America’s most notorious jail systems. Matt also explains how inmates sometimes manipulate mental health services for protection or legal advantage, what it’s like hearing confessions protected by confidentiality, and the surreal reality of assessing people just hours after seeing their alleged crimes on the news. Now running his own psychotherapy practice after leaving Rikers, Matt reflects on boundaries, trauma, and how working inside the jail changed him forever.