The heartbreaking fallout from the death of Matthew Perry is reaching its final chapter in court this week.

Perry’s longtime assistant, Kenneth Iwamasa, is set to be sentenced in Los Angeles after pleading guilty to conspiracy to distribute ketamine resulting in death. Prosecutors say he played a central role in obtaining the drugs that led to the former Friends star’s overdose in 2023.

Iwamasa was the first person involved in the case to cooperate with investigators and became a key witness during the 2½-year investigation. Prosecutors are asking for a prison sentence of just over three years, which is lighter than what he could have faced because of his cooperation.

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His lawyers argued that he struggled to say no to Perry, describing their relationship as complicated and emotionally dependent. But Perry’s family reportedly told the court they hold Iwamasa more responsible than anyone else involved, believing he was supposed to help the actor stay sober, not feed his addiction.

Perry had hired Iwamasa in 2022 and reportedly paid him $150,000 a year to live at his Los Angeles home and work as his personal assistant.

For a lot of millennials, this story still hits hard. Matthew Perry wasn’t just Chandler Bing. He was sarcasm, comfort TV, and the king of making emotional damage funny before the internet turned it into a personality trait.

The whole case feels less like celebrity gossip and more like watching a piece of your generation’s sitcom era unravel in real time.