Joyriding at 4 AM: The Damning Detail in Matthew Perry's Death

The specifics of how we fail those closest to us can be as revealing as the crime itself. In the case of Matthew Perry’s death, a damning detail emerged from a letter written by Lisa Calio, Perry’s friend and publicist of nearly 30 years, submitted ahead of sentencing for Kenneth Iwamasa, the actor’s longtime assistant.

While Iwamasa faced charges for being the middleman between drug dealers and Perry—and for administering the fatal ketamine injection that killed the Friends star in 2023—Calio’s account zeroed in on something that cuts to the heart of his betrayal. Shortly after Perry’s death, she received a text from Iwamasa at 4 AM. He was driving one of Matthew’s cars from the Hollywood Hills house to the Palisades property. And according to Calio, he was loving it.

It’s a small moment, but it speaks volumes. While Perry lay dead, his longtime assistant was joyriding through Los Angeles in the dead of night, seemingly unburdened by the weight of what had just happened. Calio didn’t mince words in her letter, describing Iwamasa’s true concern as maintaining the comfortable lifestyle he’d grown accustomed to—not protecting the man who employed him. She alleged that Iwamasa witnessed Perry seize more than once and never alerted those who cared deeply for him.

The picture that emerges is one of calculated neglect wrapped in the trappings of loyalty. Calio claims that after Perry’s death, Iwamasa persistently sought a position with the Matthew Perry Foundation, which was being built to help addicts—a foundation Calio was working to establish with Perry himself. When told no, his requests and expectations, she wrote, were outrageous.

In her closing statement, Calio was unsparing: Kenny Iwamasa killed her friend through his narcissistic, irresponsible behavior—the psychotic plan that led him to heat the jacuzzi, administer the giant shot Perry requested, and leave him alone to die. Whatever sentence he receives, she concluded, won’t be long enough. He will always be known as the man who killed Matthew Perry. Today, as Iwamasa faces sentencing with up to 15 years in prison, those words carry the weight of a friendship betrayed and a life cut short by someone who was supposed to protect it.