The prosecution’s case against a former CIA officer accused of sexually abusing more than 20 incapacitated women in Mexico City is at risk of collapsing because the Justice and State departments may have botched the execution of a warrant to seize the officer’s iPhones, court records show.
A federal judge is set to hear arguments Thursday about whether nearly 600 photos of the defendant allegedly abusing incapacitated women should be thrown out, in a dispute that could make new law on the question of what constitutes an improper search in the digital age.
The former CIA officer, Brian Jeffrey Raymond, has been held without bail in a Washington, D.C., jail for nearly three years. He made a deal to plead guilty to two counts of sexual abuse in July 2021, admitting in court to preying upon women he met in and outside the U.S. through dating sites even as he carried out his clandestine duties.
But the one-time spy withdrew his plea last year after members of his legal team realized there were significant problems with how the evidence in the case was obtained. In allowing Raymond to change his plea, the federal judge ruled that one of his former defense lawyers had been ineffective in noting major concerns about the manner in which investigators gained access to Raymond’s iPhones. The judge ruled that law enforcement agents may have violated Raymond’s rights under the Fourth Amendment, which guards against unreasonable search and seizure, and under the Fifth, which says a person can’t be forced to testify against himself.
That same judge, Colleen Kollar-Kotelly, is now set to decide whether to grant the defense’s motion to suppress nearly all the evidence in the case. If she does that, it could seriously undermine the charges against a man Kollar-Kotelly described as “a sexual predator with the means and motive to seek out unsuspecting women on dating applications, drug them, abuse them, and leave them without the memory or wherewithal to report his deviant schemes to law enforcement.”
In ruling to deny Raymond bond, Kollar-Kotelly concluded that “the video and photographic exhibits” show that the “defendant has violently enacted a fetish for unconscious women by drugging and sexually assaulting scores of women over the course of several years.” That evidence included Raymond’s interactions with hundreds of women on dating sites, photos of a sexually aroused Raymond manipulating the bodies of unconscious women, interviews with victims, and evidence that he repeatedly searched the internet using terms including “passed out girl,” “ambien and alcohol and pass out,” and “deep sleep.”
As part of his agreement to plead guilty to two charges, the FBI said, “Raymond admitted to having sexual intercourse with two of the women depicted when both were unable to appraise the nature of the conduct.” In the plea agreement, the FBI said, “He also admitted that over the course of 14 years, he recorded and/or photographed unconscious and nude or partially nude women and touched their breasts, buttocks, and/or genitalia while they were incapable of consent.”
His defense lawyers have now withdrawn that admission and dispute all charges against him (with the plea voided, he could face up to 25 counts). His attorneys also contend that all of the electronic evidence should be thrown out. They say the photos of women found on the phone were used to establish the probable cause that led to the seizure of almost all of the other key evidence in the case from Raymond’s iCloud account, his laptop and other devices.
“Mr. Raymond requests the Court to do what it must in this case — to suppress all evidence that is fruit of the poisonous tree,” defense lawyers wrote in a recent brief.
The judge agreed in a ruling that “there are viable concerns regarding the manner in which the warrant was executed” and “troubling” actions by law enforcement agents stemming from their “admitted technological ineptitude” and their failure to plan. Now she will have to decide whether those concerns amounted to impermissible constitutional violations.
Raymond’s defense lawyers declined to comment, as did the Justice Department and the State Department, whose Diplomatic Security Service agents were said by the court to have acted questionably when executing the warrant.
Legal experts consulted by NBC News were split on the likelihood that the defense will prevail.
“The defense raised several interesting, nonfrivolous questions concerning the constitutionality of the search,” NBC News contributor Chuck Rosenberg said. “In the end — and this may just be my bias as a former federal prosecutor — it seems to me that the government has the better of the argument. The search, though unusual in some ways, was conducted lawfully, and the evidence seized should ultimately be admissible.”
But Florida attorney Nellie King, president of the National Association of Criminal Defense Lawyers, had a much different view of what she called a “bungled” warrant execution.
“The government’s efforts to contort and contrive a good search out of the numerous constitutional violations committed in this case strains credibility,” she told NBC News in an email, adding that law enforcement “crossed constitutional boundaries via their numerous and desperate attempts to gain access to the phone data and in their zeal to arrest Mr. Raymond. There is ample reason for the Court to suppress the evidence, as the ends do not justify the means, no matter the type of case, or the high value target of the investigation.”
State Department agents obtained a warrant to seize Raymond’s phones after an incident in May 2020 at his government apartment in Mexico City, when police were called after a naked women emerged on his balcony screaming for help, according to court records.
He resigned from the CIA and traveled to Virginia, where the Diplomatic Security Service agents served him in June 2020 with a search warrant for his phones. Moments before they took them, he told them he had photos of unclothed women on them, court records show.
But the agents got tripped up, court records show, by their apparent lack of understanding of the layers of security on iPhones, and by the complex body of law governing how law enforcement must deal with those security measures.
The two iPhones Raymond possessed — one personal, one for work use — were locked with encryption, and could be unlocked with a passcode or fingerprint. As is standard, the warrant allowed the agents to force Raymond to use his finger to unlock the phone. But courts have held that law enforcement can’t force a target to give up his passcode, because that would violate the Constitution’s Fifth Amendment ban against forced self-incrimination.
Agents took the phones from Raymond after meeting him in the lobby of his hotel, but he had turned them off before handing them over. Accessing them at that point required the passcode, which the agents did not have. They went back to the hotel an hour later after consulting with a Justice Department prosecutor and told Raymond he was compelled to use his thumbprint to open the phones. But the agents failed to keep the phones from locking, so they went back a third time at the prosecutor’s urging, and Raymond provided his passcodes, allowing them to change the settings so they could continue to access them, court records show.
Defense lawyers argue the agents violated two cardinal rules that render the search unconstitutional. One, they say, a warrant only allows one search, except under very specific circumstances. They say that once the agents left with the phones the first time, the court-ordered search was over and the warrant was no longer valid.
Two, they say the agents badgered Raymond and made him believe he was compelled to hand over his passcode.
“The agents’ [plan] for executing the warrant shows they were doomed to fail because they had no viable plan for maintaining access after using biometrics to open the phones,” defense lawyers wrote in court papers. “Unfortunately, during the seizure the agents made matters worse by suggesting and allowing Mr. Raymond to turn his phones off, disabling biometric features, which was their only hope of gaining compelled initial access to the phones. They therefore needed PIN codes and, eventually, passwords, to get and maintain access to the phones. However, Mr. Raymond asked for an attorney and refused to provide such codes and passwords. Thwarted by Mr. Raymond’s rightful refusal to provide codes, the agents, acting on the advice of prosecutors, unlawfully and unreasonably seized Mr. Raymond and his phones two additional times until they achieved full access.”
All the encounters between Raymond and the agents were recorded. The defense points out that the agents “directly asked or suggested that Mr. Raymond give them his passcodes and passwords at least 27 times. With their insistence, Mr. Raymond finally relented and entered his PIN code and Apple password so that the agents could reset the codes and establish permanent access to the phones. Notably, although the agents blurted out that this was voluntary, they did not use a standard PIN code consent form to advise Mr. Raymond of his rights or memorialize his consent.”
In its response, the Justice Department insists the warrant execution was legal.
“There was no Fourth Amendment violation,” prosecutors say in court papers, adding that “reengaging the defendant to utilize biometrics was not a second or third seizure of the phone, but a reasonable continuation of the original seizure.”
They add that there was no Fifth Amendment violation “because the act of entering the passcodes into the phones was not a compelled self-incriminating statement to law enforcement. Moreover, the defendant was not in custody and was not coerced to provide his passcode.”
Lastly, they add, investigators, “would have inevitably been able to discover the evidence that was on the phones, and separately, the government would have inevitably discovered the hundreds of photographs and videos located on the defendant’s other devices and storage platforms.”
But even if the judge disagrees with all of that, prosecutors say, the government’s mistakes can be overlooked due to the “good faith” exception. They say there was nothing wrong with the probable cause used to obtain the warrant and no accusation the agents acted maliciously — so whatever mistakes were made were not meaningful.
The defense responded: “The good faith exception does not apply to the unlawful execution of an otherwise valid warrant. … The Supreme Court has never applied the good faith exception to excuse an officer who was negligent himself, and whose negligence directly led to the violation of the defendant’s constitutional rights.”
The government took the unusual step of acknowledging Raymond’s CIA affiliation in a 2021 request for information put out by the FBI.
“Raymond previously worked for many years at the Central Intelligence Agency (CIA),” it says. “In the United States and internationally, Raymond met many of his victims on various dating applications. He speaks both Spanish and Mandarin Chinese.”
Raymond is the second CIA case officer in recent memory to be accused of abusing incapacitated women while on assignment abroad. In 2011, a former CIA spy was sentenced to 5 1/2 years for drugging and sexually abusing an Algerian woman while he was head of the agency’s operations in that country. He had pleaded guilty after being accused of raping at least two women.