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Constitutional Seach-and-Seizure Protections May Come to the Rescue for Sexual Abuser

Criminal evidence bag with phone inside
By Eric Harvey, J.D. | Last updated on

What happens when the feds have a mountain of photo and video evidence against you for a crime, taken from your very own iPhone, but you were coerced into giving them the password? We're about to find out, in the case of ex-CIA officer Brian Jeffrey Raymond.

The former spy may get off easier than expected, as a result of a botched warrant by investigators. A federal judge is considering whether a search of his phone violated his Fourth and Fifth Amendment rights. 

Held without bail in a jail in Washington, D.C. for roughly three years now, Raymond, 45, stands accused of serially abusing women. According to court records, he may have as many as 22 victims. We covered more details of his transgressions in a separate blog post, but we'll recap them again here.

Inculpating iPhones

Prior to his resignation from the CIA in 2021, it is alleged that Raymond had made a regular practice of using dating apps to lure unsuspecting women into vulnerable situation—even while he was posted on espionage-related assignments for the Agency in Mexico City. According to the indictments, over a period of 14 years, he drugged and assaulted these women during their periods of incapacitation. And while they were unable to consent due to inebriation, it is also alleged that he created around 600 photos of his victims. 

As he was using smartphone-based dating apps in furtherance of his crimes, unsurprisingly, there's a great deal of digital data out there that serves as the exactly the kind of evidence needed to show that Raymond did what he was accused of, beyond a reasonable doubt. And FBI agents got that data. 

After an incident in May 2020, State Department agents obtained a warrant to search and seize evidence from Raymond. At that time, a woman had recently run, screaming and naked, onto the porch of the defendant's apartment in Mexico City. In responding to that incident, U.S. authorities became suspicious of the defendant, and executed a search warrant on his personal and work phones. The State Department's Diplomatic Security Service agents were tasked with collecting the evidence. The search of the phones and Raymond's iCloud account revealed hundreds of images and videos of 21 different naked, unconscious women, and even shots of Raymond actively assaulting them.

The judge overseeing the proceedings interpreted the photographs as evidence of the defendant's criminality, and used this consideration when denying him bail pending trial. She remarked that "the video and photographic exhibits" indicate 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." In July 2021, Raymond entered into a plea deal to plead guilty to two counts of sexual abuse.

That sounds like a rare story of dating apps coming to the rescue and a slam-dunk case for prosecutors, right? Well, it could have been. Unfortunately, the FBI may have dropped the ball.

A Botched Investigation

Raymond's attorneys recently filed a motion to suppress all evidence that FBI agents seized from his personal iPhone, claiming that the agents that executed the search improperly carried out their warrant. 

Raymond's iPhones, a work phone and a personal phone, were locked with encryption. Of course, they could be opened with either a passcode or his fingerprint. Under the warrant, agents were permitted to compel Raymond to unlock the phone with his fingerprint. But according to legal precedent in the United States, authorities cannot force the subject of a search to yield their passcode. Courts have decided this because forcing a suspect to give up their passcode violates the Fifth Amendment prohibition on self-incrimination.

On the first attempt, the agents requested that Raymond unlock his phones with his fingerprint. The defendant complied, and the agents seized the phones. But the phones locked again, as iPhones are programmed to do. The agents requested that he unlock the phone a second time, and he did so. But the phones locked additional times, so agents repeatedly had to ask Raymond to unlock the phones. 

Eventually, after at least 27 of such attempts, the defendant yielded his passcode to the investigators, who adjusted the settings of his phones to be able to make consistent their ability to review the contents of phones. Attorneys for the defense allege that this violates restrictions on self-incrimination under the Fifth Amendment. Neither precedent nor the search warrant permitted the agents to request and use the defendant's passcode.

Fourth and Fifth Amendment Protections

The Fourth and Fifth Amendments to the U.S. Constitution pertain to the rights of criminal defendants and those that stand accused of crimes. The two amendments provide a variety of protections for such individuals against abuses of authority by the U.S. government and its officials as those officials carry out procedure related to handlings of criminal offenses.

In essence, the Fourth Amendment prohibits unlawful searches and seizures. The Fifth Amendment requires that court systems and their officials fairly treat criminal defendants. It also protects the rights of those that stand accused of crimes from having to self-incriminate, among other things.

But how do these amendments come into play in shaping the outcome of Raymond's trial? Well, courts have long held that the appropriate remedy for violating a defendant's constitutional rights by improperly obtaining evidence is to throw out that evidence. Under what is known as the "exclusionary rule," the numerous photos, videos, and other evidence that would get a jury to convict Raymond would have to be excluded from his trial. 

Raymond's Defense

Attorneys for the defendant are not contesting that federal investigators possessed a valid warrant for conducting a search and seizure of evidence from Raymond. What they are contesting is how the investigators carried out their warrant. The crux of the issue that the judge must now consider is whether the evidence was collected illegally and in an unconstitutional way.

At the same time, Raymond's attorneys claim that search warrants, under relevant law and precedent, are only valid for one search. But, as we've discussed, agents conducted what appear to be multiple searches, as they repeatedly accessed, lost access, and then re-accessed the defendant's iPhones. Defense attorneys also claim that recordings of the interactions between the agents and their client show that "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."

Prosecutors' Response

The Justice Department has responded by saying that the warrant was executed in a legal way. They claim that no second, third, or additional searches beyond the first took place because "reengaging the defendant to utilize biometrics" do not amount to additional searches and seizures of the phones. They are that those additional re-approaches of the defendant amount only to "a reasonable continuation of the original seizure."

DOJ attorneys also argue that no violation of the Fifth Amendment right against self-incrimination occurred. They argue that because agents did not compel self-incrimination, the defendant was not "in custody" at the times of the requests for the passcode, and was never coerced. 

Prosecutors further maintain that the courts would have ultimately discovered and reviewed the contents of the phone by other means, regardless of whether the investigators had obtained a warrant or even ever conducted a search of the iPhones in the first place.

The "Good Faith" Exception

Even if the judge agrees with Raymond's arguments, the DOJ claims that the agents' errors remain inconsequential because of a legal principle known as the because of the "good faith" exception to the exclusionary rule. Under this principle, if the probable cause used to justify the search was valid and if the investigators did not act with malice, mistakes like those of the agents here are irrelevant, and the evidence could stand.

Responding to the Department's argument, Raymond's attorneys claimed that the good faith exception "does not apply to the unlawful execution of an otherwise valid warrant." They claim that 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." In other words, they argue that it makes no difference if the investigators were incompetent in their execution of the search; errors and sloppiness are no excuse, and no reason to make an an exception.

Free by a Technicality? 

The criminal proceedings against this ex-CIA officer draw attention to a variety of protections to which the accused are entitled under the Constitution of the United States. Under review now is whether a person accused of serially sexually assault women may enjoy the protections afforded to defendants during criminal proceedings. In question is whether the clearly damning evidence may continue to be used at trial against Raymond. 

Now that it has become clear that he may have a viable claim concerning how federal investigators may have violated his constitutional rights, he has withdrawn his plea deal. With the plea deal voided, he could now face up to 25 counts of sexual misconduct-related crimes.

It looks like the defendant's fate could boil down to whether the agents legally executed the warrant to search the defendant's phone. It's possible that carelessness on the part of investigators could be the path to freedom for a textbook example of a serial sex criminal.

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