Matthew Perry wanted ketamine. So his personal assistant got it for him. And on Oct. 28, 2023, according to court papers, Mr. Perry told the assistant, Kenneth Iwamasa, “Shoot me up with a big one.” Mr. Iwamasa complied.
Hours later, he said, he found Mr. Perry dead.
Two doctors, a drug dealer and an acquaintance of Mr. Perry, the actor who starred in the TV show “Friends,” have since been sentenced in the case. Mr. Iwamasa has pleaded guilty to conspiracy to distribute ketamine causing death, and prosecutors have asked that he spend 41 months in prison. On Wednesday, a judge is expected to render a sentence.
Members of Mr. Perry’s family have made clear in letters to the court that they hold no sympathy for Mr. Iwamasa. One relative called his actions a “betrayal,” noting that Mr. Iwamasa had spoken at Mr. Perry’s funeral.
“We trusted a man without a conscience,” wrote Mr. Perry’s mother, Suzanne Morrison, “and my son paid the price.”
Martin Estrada, who was the U.S. attorney for the Central District of California when that office charged Mr. Iwamasa, agreed. “His job was to assist Mr. Perry, but he did the opposite,” Mr. Estrada said.
People with experience in the industry, either as personal assistants themselves or as recruiters, also condemn Mr. Iwamasa’s behavior, saying it was an aberration in a profession full of principled employees who do not break the law. But the episode has prompted some to consider the power dynamics between influential celebrities or executives and underlings hoping to get a foot in the door.
Assistants are often chosen because they have “discretion and loyalty and confidence and exceptional judgment,” said Emily Levine, an executive vice president at Career Group Companies who specializes in staffing for high-profile clients. Those attributes, many people with knowledge of the industry concede, can convince bosses that their assistants are willing to do anything to please them.
It was in that spirit that Mr. Iwamasa’s uncle Yukio Iwamasa defended his nephew in a brief telephone interview. “He’s not a devious person,” he said. “He is somebody that follows instructions very, very sincerely, very thoroughly. And that’s the reason why he was a personal assistant. That’s the reason why he was hired and kept.”
My Dinosaur Needs a Dentist
To better understand the work, and work environments, of personal assistants, The New York Times reviewed hundreds of pages of court documents concerning several cases between assistants and their employers, and spoke with more than a dozen people who work or have worked as assistants, in Hollywood and beyond, or who have been their bosses or their headhunters. Several of those assistants were granted anonymity to speak candidly about their experiences because they had signed strict nondisclosure agreements as a condition of their employment.
A few large clearinghouses, as well as a few boutique firms, specialize in helping those seeking to hire an assistant. But many young people looking for a career break find their way to the profession through less formal routes. Some work at talent agencies before being dispatched to help a client. Others run into their eventual bosses while working a day job. A few are contacted directly on social media. Many simply get referred by a friend.
People who have worked as personal assistants for top executives and A-list celebrities emphasized that many assistants are altruistic helpers by nature — empaths who want to make things run smoothly.
But there is more to the job than “dry cleaning and errands and coffee runs,” said Meghan Grimm, the founder of Clyde Staffing and a former personal and executive assistant to Madonna and Jennifer Lawrence. The job teaches problem-solving and accountability, she and others said. Many of the assistants stressed their love for the work and their pride in performing it.
“I can do anything now,” said Ms. Grimm, whose agency has placed assistants with the likes of Dakota Johnson and Anne Hathaway. “I have a guy for everything. In New York, in L.A., I can make things happen.”
The requests sometimes border on the comedic. Some assistants compared working with their boss to coddling a child. They might need to guide their frantic client through the process of calling a cab. Or they might be required to go, in person, to wake up their boss at a hotel each morning.
One assistant described getting dozens of early-morning calls from her distraught boss, who begged her, through tears, to find a dentist for his dinosaur. After he calmed down, she came to understand what he meant: The boss had a dinosaur skeleton, apparently made of rare and expensive fossils, at his Parisian apartment. An evening of revelry had knocked out its teeth and broken its jaw.
The job can pay off. The comedian Ashley Padilla, now a star of “Saturday Night Live,” once worked as an assistant to Diane Keaton, who asked Ms. Padilla to edit one of her books. “I could do it because she believed I could,” Ms. Padilla told New York magazine this year. “Diane wanted me to succeed.”
But the work can also take a significant toll, some assistants said. Several said they were expected to be available 24 hours a day, seven days a week. To be effective, a personal assistant must be a therapist, a confidant and an emergency troubleshooter all at once, some said in interviews.
Assistants may need to live at their boss’s house for months, becoming familiar with every aspect of his or her personal life. They may be asked to drink with their star by the pool when loneliness or sorrow sets in.
A former assistant to Lady Gaga said in court papers that she often slept in the same bed as the musician so she could attend to her needs. If her boss grew tired of the DVD she was watching in the middle of the night, she would wake up the assistant to have her change it, the court papers said. (The lawsuit involved allegations of unpaid overtime wages, which lawyers for Lady Gaga denied in court papers that the assistant was owed; the parties settled out of court, documents say.)
None of the current or former assistants The Times spoke with said they had ever been asked to engage in criminal activity, including by procuring illegal drugs, for their bosses.
As for salary, recruiters say that assistants for wealthy individuals can make $150,000 to $300,000 annually. But an overwhelming majority of the positions pay less than $50,000 a year, according to a 2021 survey of Hollywood support staff members, even as those employees often live in some of America’s priciest cities.
Hollywood assistants do not have a union and often lack the infrastructure they need to help set and enforce boundaries and expectations, some said. The continued prevalence of nondisclosure agreements, they added, helps ensure that misconduct is rarely made public, except through litigation.
A onetime personal assistant for Ye, the rapper formerly known as Kanye West, has an open lawsuit against the artist alleging sexual harassment. So, too, does a former personal assistant for Marilyn Manson, who has alleged sexual abuse. Both artists have denied the allegations.
Some current and former personal assistants who spoke with The Times lamented that they had felt trapped in their work — unhappy but without prospects if they were to quit. They had been lured by hopes that their influential bosses would help them begin careers in a tough industry, they said, but that did not materialize. And they knew they were replaceable.
“Loyalty is a really good thing,” said Ms. Levine, the recruiter. “But not when you’re compromising your own gut feeling.”
‘I Thrive in Chaotic Situations’
It is not clear how Mr. Perry conceived of Mr. Iwamasa’s responsibilities. But in a sentencing memo filed this month, prosecutors said he had been “paid $150,000 per year and had various responsibilities, including those related to Mr. Perry’s medical care.” The court papers said Mr. Iwamasa “had known Mr. Perry since approximately 1992 and became his live-in assistant in 2022.” Mr. Iwamasa has not spoken publicly about his involvement in Mr. Perry’s death.
In her statement to the court, Ms. Morrison described the comfort her family felt when her son hired Mr. Iwamasa, whom the family knew as Kenny. Of her son, she explained, “In the past, when the drugs got the better of him, he hid away so that no one would know — which of course was the signal to us that it was time to get in there and get help.”
“Which is why,” she continued, “we were relieved when he took on an assistant who — he believed and we believed — understood. He had known Kenny, and so had we, for 25 years.”
According to his LinkedIn profile, Mr. Iwamasa, 61, went to high school and community college in Michigan, took some college classes in Colorado and eventually moved to Los Angeles to study cinematography. It was then that he connected with Stephen W. Sharmat, a producer who said he took him on “like an intern.”
Mr. Iwamasa was hard-working, pleasant to be around and good at his job, said Mr. Sharmat, who is now retired. Whether it was getting groceries, picking someone up or working on a computer at Mr. Sharmat’s home, Mr. Iwamasa reliably got the work done, he said.
“He’s a good guy,” Mr. Sharmat said of Mr. Iwamasa. “And if he was doing anything for Matthew Perry, he was doing it because he thought it would help him, not because he thought it would hurt him.”
Mr. Sharmat said Mr. Iwamasa eventually left to work for the producer Doug Chapin. On his LinkedIn page, Mr. Iwamasa lists himself as a 30-year employee of “Doug Chapin Management,” which, he writes, employs him as a talent manager and executive assistant to many of the company’s clients.
“I thrive in chaotic situations which call for order,” Mr. Iwamasa says on LinkedIn. “I am discreet, loyal and honor absolute confidentiality.”
Mr. Iwamasa, his lawyers and Mr. Chapin did not respond to requests for comment.
Law enforcement officials have said that Mr. Perry appeared to become increasingly reliant on ketamine near the end of his life, and eager to find illegal sources of the drug after doctors at a local clinic refused to increase his dosage. In the fall of 2023, Mr. Perry asked Mr. Iwamasa to get him ketamine illegally, according to Mr. Iwamasa’s plea agreement.
In his final month with Mr. Perry, prosecutors say Mr. Iwamasa worked with a doctor, Salvador Plasencia, and an associate, Erik Fleming, to illegally obtain ketamine that he or a doctor could inject into the actor. Mr. Fleming obtained the ketamine he delivered to Mr. Iwamasa from a drug dealer, Jasveen Sangha. Mr. Perry, through Mr. Iwamasa, would ultimately pay Mr. Plasencia about $57,000 for 20 vials and multiple tablets of ketamine over a period of a few weeks, according to court papers.
An indictment said the group of men used coded language to discuss drug deals, referring to bottles of ketamine as “Dr Pepper,” “cans” and “bots.” Mr. Iwamasa bought some of the vials after midnight at the Santa Monica Pier, according to court documents. At one point, he drove Mr. Perry to a parking lot in Long Beach, Calif., so Mr. Plasencia could inject Mr. Perry with ketamine in the back seat.
In the five days leading up to his death, Mr. Iwamasa injected Mr. Perry with at least 27 shots of ketamine, including at least three shots on the day he died.
Sheelagh McNeill contributed research.
Matt Stevens is a Times reporter who writes about arts and culture from Los Angeles.
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