LOS ANGELES — The man and the woman had connected through the dating app Tinder and chatted on WhatsApp before eventually meeting in person for a date.

He arrived with wine in his backpack; later, they withdrew to his Mexico City apartment.

The next thing she knew, the woman was crying in the back of an ambulance, according to court documents recounting the events of their date on May 31, 2020.

The woman had no memory of screaming from the man's balcony while nude or having sex with him, which he later told authorities was consensual. The man, Brian Jeffrey Raymond, worked for the CIA and was stationed at the U.S. Embassy in Mexico.

He told investigators that he hardly used dating apps, but allowed investigators to search his phone.

That's when police discovered a horde of explicit images and videos of unconscious women, on not just his phone but also other devices he used. Eventually, authorities learned that Raymond had drugged and sexually abused multiple unconscious women across multiple countries.

On Wednesday, Raymond, 48, was sentenced to 30 years in federal prison for his crimes, the Department of Justice announced in a news release. While Raymond was a resident of Washington, D.C., and traveled extensively for his work and leisure, he was also a resident of La Mesa in San Diego County.

Raymond pleaded guilty in November 2023 to multiple sex crimes and admitted to taking over hundreds of images on his phone of unconscious women, according to federal prosecutors. Almost all of the women in the photos and videos had no memory of being recorded or being intimate with Raymond.

Prosecutors said Raymond preyed on his victims for 14 years, from 2006 to 2020, according to the dates in photographs recovered from his phone, iCloud account and other devices.

Federal authorities referred to him as a serial sexual offender who was finally exposed on the evening the unnamed woman screamed from his balcony. Police who responded to his home that night said the woman was unable to walk, appeared heavily intoxicated and later tested positive for cocaine and other drugs. She claimed she never used drugs and had no memory of having sex with Raymond.

During their investigation, authorities found that Raymond tried to delete photos on his phone, some of which showed him lying in bed next to unconscious women on two different occasions. In one video, Raymond filmed himself manipulating a woman's eyelids and stroking her, according to court records.

Investigators also found that Raymond made internet searches on his devices for information about unconscious women and the side effects of prescription drugs combined with alcohol. Those searches included "ambien and alcohol side effects," "Ambien dissolve," "Ambien and alcohol pass out" and "passed out and carried," according to court records.

During his sentencing, a federal judge ordered Raymond to pay $260,000 to his victims. He will also be required to register as a sex offender after his prison sentence is completed, the Department of Justice announced.

As part of a plea deal, Raymond pleaded guilty to one count each of sexual abuse, abusive sexual contact, coercion and enticement, and transportation of obscene material. He admitted to drugging and engaging in nonconsensual sexual acts with four women and having nonconsensual sexual contact with six women. He also admitted to drugging and then creating obscene material depicting 28 women without their knowledge or permission and drugging two other women, court records show.

"When this predator was a government employee, he lured unsuspecting women to his government-leased housing and drugged them," U.S. Atty. Matthew M. Graves said in a statement. The 30-year sentence "ensures that the defendant will be properly marked as a sex offender for life, and he will spend a substantial portion of the rest of his life behind bars," Graves said.

The case was investigated by the U.S. Department of State's Diplomatic Security Service, the FBI, the Justice Department and other federal agencies.

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