‘Shoot Me Up With a Big One’: The Pain of Matthew Perry’s Last Days

On the day Matthew Perry died, his live-in personal assistant gave him his first ketamine shot of the morning at around 8:30 a.m. About four hours later, while Mr. Perry watched a movie at his home in Los Angeles, the assistant gave him another injection.

It was only about 40 minutes later that Mr. Perry wanted another shot, the assistant, Kenneth Iwamasa, recalled in a plea agreement that he signed.

“Shoot me up with a big one,” Mr. Perry told Mr. Iwamasa, according to the agreement, and asked him to prepare his hot tub.

So Mr. Iwamasa filled a syringe with ketamine, gave his boss a third shot and left the house to run some errands, according to court papers. When he returned, he found Mr. Perry face down in the water, dead.

Mr. Iwamasa was one of five people who the authorities in California said this week had been charged with a conspiracy to distribute ketamine, a powerful anesthetic, to Mr. Perry. The defendants also included two doctors, a woman accused of being a dealer and an acquaintance who pleaded guilty to acting as a middleman.

Mr. Perry, a beloved figure who rose to fame playing Chandler Bing on the sitcom “Friends,” had long struggled with addiction. Court papers filed in the case shed light on the desperate weeks leading up to Mr. Perry’s death on Oct. 28 at the age of 54.

In his last days, law enforcement officials said, he appeared to become increasingly reliant on ketamine, and eager to find illegal sources of it after doctors at a local clinic had refused to increase his dosage.

There were warning signs that it was dangerous. The court papers refer to several instances in which Mr. Perry experienced adverse effects from the drug, including when his assistant found him unconscious at his home and observed him losing the ability to speak or move after a large dose.

In the indictment, which followed a seven-month investigation and grand jury proceedings, prosecutors accused several of the defendants of enabling Mr. Perry’s ketamine use despite being aware of his history of drug abuse and addiction, and his attempts to stay sober.

This account of Mr. Perry’s last days was drawn from the indictment and from the plea agreements reached by Mr. Iwamasa and two of the other defendants. Efforts to reach the defendants were unsuccessful; on Thursday, Dr. Salvador Plasencia and Jasveen Sangha, whose trials are scheduled for October, pleaded not guilty.

“These defendants took advantage of Mr. Perry’s addiction issues to enrich themselves,” Martin Estrada, the United States attorney for the Central District of California, said at a news conference Thursday in downtown Los Angeles.

“They knew what they were doing was wrong,” he continued. “They knew what they were doing was risking great danger to Mr. Perry. But they did it anyway. In the end, these defendants were more interested in profiting off Mr. Perry than caring for his well-being.”

‘I Just Ran Out’

As Mr. Perry’s personal assistant, Mr. Iwamasa was tasked with coordinating his doctor’s appointments and making sure he took the proper medication.

Ketamine, a strong anesthetic with psychedelic properties, is sometimes used as an alternative therapy for depression, anxiety and other mental health problems. It is also used recreationally.

Mr. Perry had earlier pursued ketamine therapy, law enforcement officials said. But when doctors at a local clinic refused to increase his dosage, they said, he sought the drug elsewhere. In September, Mr. Perry asked Mr. Iwamasa to procure him ketamine illegally, according to the plea agreement.

Mr. Iwamasa was introduced to Dr. Salvador Plasencia, a physician who was later charged in the case, as he sought the drugs.

At one point Dr. Plasencia mused on the money he stood to make with a friend, Dr. Mark Chavez. “I wonder how much this moron will pay,” Dr. Plasencia texted Dr. Chavez, who prosecutors said later supplied him with a total of 22 vials of ketamine and ketamine lozenges obtained through a fraudulent prescription for the drug. “Lets find out.” Dr. Chavez agreed to plead guilty to one count of conspiracy to distribute ketamine.

Dr. Plasencia, known as “Dr. P.,” soon instructed Mr. Iwamasa on how and where to inject ketamine into Mr. Perry’s body.

“Found the sweet spot but trying different places led to running out,” Mr. Iwamasa texted Dr. Plasencia on Oct. 4, according to court documents.

Over the next several days, Mr. Iwamasa’s requests for ketamine became more urgent.

“I just ran out,” Mr. Iwamasa texted the doctor, who replied he had two vials to sell him if the assistant could meet him in downtown Santa Monica.

That week, Dr. Plasencia met Mr. Perry and his assistant in a parking lot near an aquarium in Long Beach, Calif. He injected the actor in the back seat of the car, passing along multiple additional vials. Mr. Perry would ultimately pay at least $55,000 to Dr. Plasencia for ketamine over a period of about a month, according to court papers.

Searching for a New Supply

The actor and his assistant were beginning to look for additional sources to keep up their supply of the drug.

Mr. Perry began communicating with a man named Erik Fleming, with whom he shared a mutual friend. Mr. Fleming, who later agreed to cooperate with law enforcement, texted Mr. Perry on Oct. 10 that he could sell him ketamine at a “good price,” as long as he received a tip for brokering the deal.

Mr. Fleming was put in touch with Mr. Iwamasa to work out the details, texting him an image of a ketamine vial with a photograph of a horse on the packaging. (The drug is commonly used as a veterinary tranquilizer.)

The next day, Mr. Fleming showed Mr. Iwamasa screenshots of his communications with his source, a woman named Jasveen Sangha, whom Mr. Fleming described as working with “high end” clients and celebrities. “If it were not great stuff she’d lose her business,” Mr. Fleming wrote of Ms. Sangha’s supply.

Mr. Iwamasa texted Mr. Fleming that his boss was “only interested in the unmarked ones not the horsey version,” according to court papers.

“I did some calling around about the Mexican stuff and it’s fine for people too,” Mr. Fleming later responded.

On the same day that Mr. Perry received a legal ketamine infusion treatment from another doctor at a medical office, Dr. Plasencia visited Mr. Perry’s home and administered him a “large dose” of ketamine, according to Mr. Iwamasa’s account to law enforcement. Mr. Perry froze up, was unable to speak or move, and experienced a spike in blood pressure; Mr. Iwamasa and the doctor struggled to move him onto a couch.

Dr. Plasencia “stated something to the effect of, ‘let’s not do that again,’” the court papers said. But he continued to offer more ketamine, the papers said.

The next day, Mr. Fleming delivered a sample vial of ketamine to Mr. Perry’s home for $180. Satisfied with the drug, Mr. Iwamasa asked for more. Mr. Fleming delivered 25 vials for $6,000, including $500 for his own work, on Oct. 14.

Ten days later, Mr. Fleming delivered another 25 vials, along with ketamine lollipops that Ms. Sangha included as a bonus.

Mr. Iwamasa and Mr. Fleming both agreed to sign plea agreements, giving officials a window into Mr. Perry’s final days. Dr. Chavez eventually began cooperating with law enforcement as well. Mr. Iwamasa faces up to 15 years in prison, Mr. Fleming up to 25 years and Dr. Chavez up to a decade.

A Half-Dozen Shots per Day

In the final days leading up to the actor’s death, Mr. Iwamasa injected Mr. Perry six to eight times per day. At least twice, he found Mr. Perry unconscious at his home, the assistant told law enforcement.

On Oct. 28, after giving Mr. Perry three shots and later finding him dead, Mr. Iwamasa cleaned up the bottles and syringes left in the house, according to Mr. Fleming’s account of a conversation they later had. Mr. Iwamasa later told law enforcement officials that all of the injections administered that day had come from the supply delivered by Mr. Fleming.

That day Ms. Sangha deleted her text messages with Mr. Fleming from the app Signal and instructed him to “delete all our messages,” according to law enforcement officials.

In a text message, Mr. Fleming assured Ms. Sangha, who prosecutors said was known as “the Ketamine Queen,” that he was “90% sure everyone is protected,” saying he had dealt only with Mr. Perry’s assistant, not Mr. Perry.

“Does K stay in your system or is it immediately flushed out,” Mr. Fleming asked her.

In December the Los Angeles County medical examiner’s office said that Mr. Perry had died of the “acute effects” of ketamine. The autopsy report noted that the level of ketamine found in his blood was equivalent to the amount used for general anesthesia.

Jill Cowan contributed reporting from Los Angeles. Kirsten Noyes contributed research.