Two decades ago, Shahawar Matin Siraj started to feel uneasy about a plan to bomb a subway station in Manhattan. Osama Eldawoody, a New York City Police Department informant recruited after 9/11, had established himself as a father figure to Siraj, who was 21 when they met. Eldawoody was almost twice his age. He had shown Siraj graphic visuals of Muslims being tortured and told him that suicide bombings were forbidden but “killing the killers” was not.
Siraj eventually introduced Eldawoody to a friend, James Elshafay, who was 19 at the time. Elshafay started suggesting actual targets, such as bridges and police precincts. Siraj offered an alternative: the Herald Square subway station. Eldawoody told Siraj that the “Brotherhood” wanted to support his plan.
But as it started to feel real, Siraj tried to back out — insisting about 18 times that he was not willing to place bombs in the station. “I have to, you know, ask my mom’s permission,” he had said — suggesting that the most he would be comfortable with would be acting as a lookout. Siraj and Elshafay were arrested a week later.
Elshafay pleaded guilty and was sentenced to five years in prison and three of supervised release. Siraj decided to fight the charges, went to trial, and was sentenced in 2007 to 30 years in prison after three years of pretrial detention.
Now, after serving more than 75 percent of his sentence, he and his lawyers at CLEAR, a legal nonprofit and clinic at the City University of New York, are fighting for his compassionate release.
Photo: Courtesy of the Siraj family
Opening arguments took place on Wednesday before the U.S. Court of Appeals for the 2nd Circuit in Manhattan, where Siraj’s legal team is appealing a March 2023 decision from the U.S. District Court for the Eastern District of New York denying that request. Siraj’s lawyer, Mudassar Hayat Toppa, a staff attorney at CLEAR, argued that he deserves compassionate release for many reasons, especially his youth and vulnerability at the time. A forensic psychologist, arranged by the defense to evaluate Siraj for sentencing, had previously said that he had impaired critical thinking and analytical skills. “Based on his intellectual limitations … he is susceptible to the manipulations and demands of others,” the expert noted. Even Siraj’s family described a somewhat childlike demeanor; his sister mentioned that before his arrest he would watch cartoons and play video games, particularly Pokémon, everyday.
The defense also pointed on Wednesday to Siraj’s efforts at rehabilitation, including how he put his own safety at risk to protect a federal corrections official from an act of violence from another inmate. They emphasized the significantly shorter sentence given to his co-defendant; difficult prison conditions, including four years at the Communications Management Unit at FCI-Terre Haute; and the discriminatory police surveillance that led law enforcement to him. Rather than considering these reasons holistically, the district court denied his motion by evaluating each one in isolation, they argued. The prosecution refuted this argument on Wednesday, with lawyer Nina Gupta saying that the government did not view each reason in isolation. In a legal brief, they cited a map that Siraj had drawn of the subway station and that he failed to meet the heavy burden of proof showing that the district court “made a clearly erroneous assessment of the evidence.”
Siraj is one of almost 1,000 terrorism defendants prosecuted by the U.S. since 9/11, according to an Intercept database that was last updated in June 2023; more than 350 defendants’ cases involved FBI stings with an informant or undercover agent. The fear of this kind of surveillance transformed the social fabric of Muslim communities and made them more insular.
“You didn’t know if the person you’re talking to was an informant or undercover,” says Fahd Ahmed, executive director of Desis Rising Up and Moving, or DRUM, which represents low-wage South Asian and Indo-Caribbean immigrants, workers, and youth in New York City. (Siraj’s family are members.) A 2014 Human Rights Watch report closely reviewed 27 federal prosecutions involving 77 defendants and found that in some instances, “the FBI may have created terrorists out of law-abiding individuals by suggesting the idea of taking terrorist action or encouraging the target to act.” The report also described a pattern of targeting people with mental or intellectual disabilities in these stings.
Siraj’s counsel — like many others — had tried and failed in proving their earlier assertions of entrapment in court. Despite reports documenting the invasive role of law enforcement in encouraging crime, winning a legal case using an entrapment defense is essentially “impossible,” says Kathy Manley, legal director for Coalition for Civil Freedoms, a nonprofit organization that advocates for people they believe have been targeted in terrorism cases as part of the broader “war on terror.” Manley explains that’s because prosecutors just need to find that an individual is predisposed to commit a crime in order to rule out entrapment. They can do that by showing that the defendant failed to remove themselves from the situation or by pointing to political statements, Manley says. In Siraj’s case, the prosecutors considered his empathy for Palestinian suicide bombers living under occupation and his fascination with Osama bin Laden.
In asking for compassionate release, CLEAR is not attempting to relitigate the court’s verdict on entrapment. The lawyers tried on Wednesday to clarify a letter written by Siraj that they say the district court “erroneously interpreted.” The defendant had written in a letter to the court, “I knew I would never have been involved in any terrorist plot had I never met the informant, but I also knew I had made some terrible mistakes.” The district court concluded that “such an assertion is not an acceptance of responsibility, but an attempt to shift blame for extraordinarily serious conduct and to relitigate the underlying facts of his case” — and in particular, “the jury’s rejection of his entrapment defense.”
This reasoning was used to reject arguments highlighting Siraj’s rehabilitation, age, and unique vulnerabilities, since the district court perceived this “unwillingness to accept responsibility” as evidence that Siraj is not sufficiently remorseful, after 17 years in prison, for his actions. CLEAR highlighted several other explicit admissions of responsibility and remorse for his role in the conspiracy. “I also know that I am ultimately responsible for my actions and the consequences that resulted from them,” Siraj had written.
Compassionate release has been granted in similar cases before, albeit rarely. Last July, a U.S. district judge ordered the release of three men convicted in a terrorism sting, saying that “the real lead conspirator was the United States.” Three men from the “Newburgh Four” were freed after the judge found that they were little more than “petty criminals” and that FBI agents had been the major driver of a supposed plot to blow up synagogues in New York and shoot down official planes.
Photo: Courtesy of the Siraj family
After Wednesday’s trial, Siraj’s lawyer said that evidence of his client’s rehabilitation is among the most compelling he’s seen in compassionate release cases. “This case is important not just for Siraj,” Toppa said, “but also for others serving long sentences on terrorism-related convictions, whose redeeming conduct and statements during their incarceration are scrutinized to an unreasonable degree and dismissed by courts seemingly because of the nature of their offense.”
As Siraj waits for the court’s verdict, he has now spent 20 of his 42 years behind bars. His family is shattered too. After Siraj’s arrest in 2004, community members, including some relatives, pulled away and avoided visiting their home or saying hello on the street, says Ahmed, the director of DRUM. That’s a common dynamic with families whose loved ones have been charged with terrorism in cases involving informants. “They’re worried about getting painted as terrorism sympathizers,” Ahmed says. As for Siraj’s mother, Ahmed says she rarely leaves her home because she doesn’t want to miss a phone call from him.
