Are Federal Sting Operations in Counterterrorism Cases Legal?

Sting operations — in which law enforcement either creates or exploits a targeted likely offender’s opportunity to commit a crime — have been used by U.S. agencies for decades. And they’ve been the subject of debate for nearly as long.

Experts say federal stings increased after 9/11, in cases such as the one examined by the new FRONTLINE documentary In the Shadow of 9/11, directed by Dan Reed (Leaving Neverland). The film explores how an FBI sting led to the prosecution of the so-called Liberty City Seven, a group of Miami men charged in a 2006 Al Qaeda plot, despite having no connection to the terror group.

Some critics say that, as the FBI’s role evolved in the wake of the September 11 attacks, so too did the nature of counterterrorism stings, with the line between investigator and instigator sometimes becoming blurred. Are stings legal? And who’s most affected by them, post-9/11? Here’s a look at the legality of sting operations and how they’ve been used in the 20 years since 2001.

What laws govern sting operations?

Stings are not governed by laws passed by Congress but by guidelines first mapped out by the U.S. attorney general in 1976. Since then, those guidelines have been revised multiple times, with further guidance added that can be updated without notice.

If the Department of Justice’s Office of the Inspector General finds that the guidelines have been violated, the IG might criticize the FBI, but those are “only shaming devices,” according to Michael German, a former FBI undercover agent and a fellow with the Brennan Center for Justice’s Liberty & National Security Program who appears in In the Shadow of 9/11.

Courts can also play a role, including if the inspector general finds possible criminal conduct.

U.S. Attorney General Edward H. Levi originally created the guidelines in response to Watergate revelations of federal privacy and free-speech violations targeting activists including Martin Luther King Jr., as well as members of the Black Panthers, the Socialist Workers Party in the U.S. and the KKK.

Attorney General John Ashcroft revised the guidelines in 2002, with further changes from Attorney General Michael Mukasey in 2008. To “clarify and enhance” the guidelines, the FBI introduced its Domestic Investigations and Operations Guide, or DIOG, in 2008, with further updates in 2011, 2013 and 2016. Ashcroft also created guidelines for undercover FBI operations in 2002, and Attorney General Alberto Gonzales added guidelines on the use of “confidential human resources,” or informants, in 2006.

Only redacted portions of the 2016 DIOG are available, although The Intercept published a leaked version of what it identifies as the entire DIOG.

Why so many changes? What did they do?

After 9/11, the FBI shifted its focus from organized crime and drug trafficking to terrorism, according to Hugh Handeyside, now a senior staff attorney with the ACLU’s National Security Project and formerly a CIA analyst in the Directorate of Intelligence and the Counterterrorism Center. 

“It defined itself more as an intelligence-gathering agency, in addition to a criminal investigative agency,” Handeyside says of the FBI.

“That changed because of 9/11, because there was fear,” says Jesse Norris, an assistant professor of criminal justice at State University of New York at Fredonia who has published extensively on post-9/11 prosecutions.

The agency also broadened its operational guidelines to reflect its new counterterrorism mandate. The 2002 changes authorized FBI agents to attend public events and protests without disclosing their identities and extended the time period for “preliminary investigations,” which require only an allegation — not the “specific and articulable facts” required by the original Levi guidelines.

Practically speaking, that meant the agency could conduct investigations without a reasonable indication that someone was engaged in wrongdoing, German says.

The 2008 changes created a new category that troubled civil liberties lawyers: “assessments,” or investigations that lack any allegation, information or reasonable indication that the subject did anything wrong and that have no time limit. And with the 2011 version of the DIOG, the FBI granted itself the power to conduct database searches without opening assessments, among other changes.

“With lower evidentiary standards, the new guidelines allowed the FBI to initiate investigations of people they have no factual basis to believe are doing anything illegal … rather than investigating evidence of actual violence committed by individuals or groups, or other illegal terrorist activity,” German told FRONTLINE.

Read more: ‘A Complex Truth’: Dan Reed on the Liberty City Seven and Counterterrorism in His New Doc, ‘In the Shadow of 9/11’

“After 9/11, a lot of people believed there were sleeper cells that were going to commit another attack,” Norris says.

A 2014 report by Human Rights Watch and Columbia Law School’s Human Rights Institute found that “at times, in aggressively pursuing terrorism threats before they even materialize, U.S. law enforcement overstepped its role by effectively participating in developing terrorism plots.”      

The FBI did not respond to individual questions from FRONTLINE. In a statement, a representative from the Office of Public Affairs wrote: “All FBI operations are conducted in accordance with all legal requirements, to include the Constitution, the Privacy Act of 1974, our Domestic Investigations Operations Guide, the Justice Manual, and the standards with which the American people expect the FBI to protect them. Additionally, all FBI operations are subject to robust compliance mechanisms and oversight from the three branches of government.”

Since 9/11, who has faced terrorism charges based on stings?

The FBI categorizes “terrorism” in two ways. “International terrorism” involves any ideology considered “foreign in nature,” such as Al Qaeda, ISIS or the FARC in Colombia, even if all parties under investigation are located within the United States. “Domestic terrorism” is typically reserved for investigations of violent criminal acts related to racial bias, antigovernment sentiment, the environment and animal rights and abortion, among others.

Most prosecutions stemming from international-terrorism sting operations since 9/11 have resulted in two types of charges: material support (69%) and criminal conspiracy (21%), according to a database maintained by journalists Trevor Aaronson and Margot Williams of The Intercept.

A number of things can be considered material support: sending money to a designated terrorism organization or providing personnel to a terrorist organization, in the form of one’s self.

Conspiracy is a charge applied when two or more people allegedly agree to commit a crime. In most jurisdictions, “you have to show something in addition to that … something minor, like buying supplies, or maybe just driving by the place you plan to attack and looking at it, seeing what it looks like — you know, some preparation to commit a crime,” says Norris, of SUNY.

According to The Intercept journalistsdatabase, the DOJ indicted 972 defendants on charges related to international terrorism between September 11, 2001, and May 14, 2021.

In a separate study from 2018, Norris and co-author Hanna Grol-Prokopczyk analyzed 580 terrorism cases dating from 9/11 to 2014 and identified 316 defendants, or 54%, where cases involved informants or undercover agents.

Norris and Grol-Prokopczyk developed 20 different indicators to track people charged with crimes related to terrorism and found that “minority racial and religious groups, undocumented immigrants, and individuals with low socioeconomic status all have elevated risk for at least one entrapment-related outcome.”

The most consistent predictor of sting targets was “Black Muslim identity,” according to Norris and Grol-Prokopczyk. They found that Black Muslims were more than three times as likely as white non-Muslims to have eight or more entrapment indicators. Of the 309 defendants targeted by stings whom the researchers analyzed (excluding seven cases due to variations), they found that 188 were Muslim.

Have defendants used entrapment as a defense?

The attorney general’s guidelines and DIOG prohibit government misconduct and entrapment, but the legal definition of entrapment is narrow.

“There is not exactly an official definition, because it was created by Supreme Court decisions, not by legislation,” Norris says, citing 1992’s Jacobson v. United States as a key case.

In court, defendants have the burden of proving they were entrapped, and a jury has to decide, beyond a reasonable doubt, whether or not the accused was predisposed to commit the crime before being approached by law enforcement.

Read more: A Major Terror Plot Interrupted — or a ‘Setup’?

“You’re not supposed to entrap people, but … predisposition is a very vague concept,” Norris says. He says that Canada, for example, has a stricter definition of entrapment. “If you get someone to commit an offense, and they weren’t already committing a crime when they started, then they are entrapped,” he says.

“There are larger legal and constitutional constraints, like the Fourth Amendment protections [which prevent unreasonable searches and seizures] that apply in a criminal proceeding, but those do not stand in the way of what the FBI has been doing in sting operations,” says Ramzi Kassem, a law professor at City University of New York and director of the school’s CLEAR Project, a nonprofit legal clinic focused on law-enforcement accountability.

“The current sting model was designed to fit within the existing framework, allowing for what many would view as troubling overreach by the FBI,” Kassem says.

No U.S. federal terrorism case has been acquitted solely on entrapment grounds, according to Norris’s research. He did find in a 2019 analysis that three defendants were acquitted after raising the issue in court, without formally introducing the entrapment defense.

Norris’s research showed that, from 2001 to 2014, most defendants pleaded guilty or took a plea deal, and only 33% of 316 cases that involved sting operations went to trial. Among those, 29 of the cases used an entrapment defense.

How does the DOJ oversee the use of informants in sting operations?

According to German of the Brennan Center, the Office of the Inspector General — part of the DOJ, which also oversees the FBI — is limited to reviewing FBI paperwork on compliance with informant guidelines.

“There is virtually no independent oversight, particularly when the FBI uses informants who have very serious criminal records, targeting people who do not have records nearly as serious as the informant,” German says. “That’s quite problematic.”

A special report released in 2005 by the Office of Inspector General found that informant guidelines — such as FBI agents obtaining the proper authority to permit engagement in otherwise illegal activities, documenting an agent’s evaluation of an informant and giving the required instructions to informants, among others — were violated in 87% of cases.

In a 2019 audit, the Office of Inspector General cited the FBI’s current validation process for informants as lacking “sufficient independent headquarters oversight.”

In a statement, a representative from the FBI Office of Public Affairs told FRONTLINE: “The FBI’s mission is to protect the American people and uphold the Constitution. That mission is dual and simultaneous, not contradictory, which means that one part need not — and must not — come at the expense of the other.”

Watch In the Shadow of 9/11, in full, below.


Paula Moura

Paula Moura, Tow Journalism Fellow, FRONTLINE/Newmark Journalism School Fellowship, FRONTLINE