How the case of conflicted teenager Mohamed Mohamud — convinced by the FBI he was bombing a Christmas tree lighting ceremony in Portland, Oregon — could determine whether the American government is allowed to spy wholesale on its citizens.

On Nov. 4, 2010, a small cell of al-Qaeda operatives convened at a Starbucks in Corvallis, Oregon, to review the details of their plot to kill 25,000 people in downtown Portland. The cell had three members: Hussein, an explosives expert; Youssef, a businessman turned jihadi recruiter; and Mohamed Osman Mohamud, a 19-year-old Somali-American college student.

The would-be terrorists had met earlier that year, after one of Mohamud’s friends from the mosque recommended him to the Council, a secret jihadi organization that scoured the globe for potential operators. Hussein and Youssef flew to Oregon to meet the teen, whom they called “a jewel in the rough.” Together, the three conceived a plot to detonate an 1,800-pound bomb during Portland’s Christmas tree lighting ceremony, a yearly Black Friday tradition in Pioneer Square, the city’s main plaza. Mohamud chose the target. Hussein and Youssef designed and built the bomb.

It was time for a test run. After meeting at the coffee shop, the group drove to a remote spot in the countryside. There, Hussein showed Mohamud a smaller version of the device: a backpack filled with three pounds of explosives. They placed the bomb in a tree and walked away. Hussein handed Mohamud a cell phone and asked him to dial a number. The teenager obeyed — and a small explosion rattled the last yellow leaves on the trees.

Later that day, the cell returned to Mohamud’s apartment in Corvallis to record his farewell video. The teenager put on a white robe, a white-and-red headdress, and a camouflage jacket. He began to read his manifesto to the camera. “For as long as you threaten our security, your people will not remain safe,” Mohamud said. “As your soldiers target our civilians, we will not fail to do so. Did you think that you could invade a Muslim land and we would not invade you?”

Two weeks later, on Nov. 26, 2010, Youssef picked up Mohamud from a friend’s house in Portland. They met with Hussein and headed to a parking spot near the Comcast building, where the operators showed Mohamud a large white van. Hussein opened the side door, revealing six 55-gallon drums filled with fertilizer. On the front seat was the detonation mechanism: a cell phone, a 9-volt battery, and a switch. The whole van smelled of diesel.

“It’s beautiful,” Mohamud said.

The three headed to a hotel in downtown Portland, where they prayed and ordered a pizza. They turned on the TV and watched the crowds march into Pioneer Square under light rain.

Around sunset, Hussein and Mohamud drove the bomb to the chosen corner. Mohamud flipped the toggle switch attached to the detonator, arming the bomb. Youssef picked up Mohamud and Hussein in a different car and drove them to Union Station. As the three left the scene, Mohamud said he thought he saw his mother heading toward the ceremony.

After dropping off Youssef at the train station, Hussein and Mohamud parked in a nearby garage. The explosives expert handed the teen a cell phone. The teenager dialed the detonator number. Nothing happened.

“Why don’t you get out of the car and try again?” Hussein said.

Mohamud did as he was told. As he pressed the last button, he heard a group of people running at him.

“Don’t move!” someone yelled.

Suddenly, Mohamud was on the ground. He could hear Hussein screaming, “Allahu akbar!” — God is great — over and over again. After the third or fourth time, the 17 arresting officers started to laugh.

The bomb Mohamud had tried to detonate was fake. The test explosion was staged. There was no secret council of militant leaders seeking a gifted Somali-American teenager to wage jihad. Youssef and Hussein were undercover FBI agents.

The Black Friday non-bombing of Portland was a federal government sting, the result of a yearlong operation involving dozens of people, a secret court order, and a massive surveillance apparatus.

Mohamud’s mugshot. Multnomah County Sheriff Office via Getty Images

Mohamud went to trial three years after his arrest. (Unless otherwise stated, the facts in this article come from the voluminous public record for his criminal case, including the 2,700-page trial transcript, as well as firsthand interviews with 11 people with knowledge of the case. The FBI, the Department of Justice, and Mohamud’s attorneys declined to answer detailed questions. Mohamud did not respond to letters sent to him in prison.)

In court, Mohamud’s lawyers attempted an entrapment defense, arguing that their client never indicated he wanted to attack Portland before the FBI contacted him. The prosecution said Mohamud’s prior correspondence with two individuals suspected of working for al-Qaeda was evidence he was looking for “the right people” — and that, had the FBI not intervened, he might have found them.

The jury convicted Mohamud. A judge sentenced him to 30 years in prison.

The story could have ended there. But, months after the trial, Mohamud’s lawyers received an unexpected message from the government: At some point in the investigation, the FBI had used the 2008 amendments to the Foreign Intelligence and Surveillance Act, a law known as the FAA, to access Mohamud’s communications without a particular warrant.

Mohamud is the very first defendant to​ potentially challenge the NSA’s mass surveillance programs revealed by Edward Snowden before the U.S. Supreme Court.

The notification was bewildering. The government is supposed to inform defendants they have been targeted by FAA spying before they go to trial, not after. More broadly, the Fourth Amendment to the Constitution — at least as many legal experts understand it — protects citizens and those living in the U.S. from warrantless surveillance.

Today, Mohamud’s lawyers are asking the 9th Circuit of the U.S. Court of Appeals to overturn their client’s conviction. Their central argument is that the FBI’s use of the FAA against Mohamud violated the Constitution.

Mohamud is the very first criminal defendant to challenge the FAA before a court of appeals, which opens the door for a hearing before the U.S. Supreme Court. The appeal has widespread implications: The controversial law provides the legal framework for the mass surveillance programs that Edward Snowden revealed in 2013.

“It’s not an exaggeration,” Patrick Toomey, an American Civil Liberties Union attorney, told BuzzFeed News, “to say that the privacy rights of millions of Americans potentially hang in the balance of his case.”

Marc Aspinall for BuzzFeed News

The chain of events that led to Mohamud’s appeal began in 1978, when Congress passed the Foreign Intelligence and Surveillance Act, or FISA. In its original version, the law forbade the government from spying within U.S. territory, unless it could convince a special court that the investigation’s targets were “agents of a foreign power.”

The law was far from perfect: The special court met in secret and approved nearly all of the government’s requests. (Of the 35,333 applications for FISA warrants filed between 1979 and 2013, only 12 were rejected outright.) Still, the act required the government to name the individuals it was targeting, specify the kind of communications it wanted to intercept, and give a timeline for the investigation — provisions that generally kept it in line with the Fourth Amendment.

Instead of targeting individuals already engaged in criminal conduct, the FBI after Sept. 11, 2001, began focusing on people who it believed could potentially become terrorists.

All of that changed after Sept. 11, 2001. Instead of treating terrorism as a crime to be solved after it happened, the government began to treat it as a disaster to be prevented. In 2002, President Bush signed a secret executive order authorizing the National Security Agency to monitor every email, telephone call, and text message in which at least one party was believed to be outside the U.S. — even if everyone else in the conversation was located within the country. The administration said the NSA didn’t need any kind of warrant, from the FISA court or otherwise, because such communications counted as “foreign” rather than “domestic,” and were therefore not protected by the Fourth Amendment.

The FBI, however, faced a problem: All that monitoring of communications was turning up a lot of terrorist sympathizers, but not a lot of actual criminal activity. The bureau responded by refining one of its most controversial techniques: the sting operation. Instead of targeting individuals already engaged in criminal conduct, the FBI began focusing on people who it believed could potentially become terrorists.

Underlying many of these sting operations was a psychological doctrine — strongly challenged by several studies — known as “radicalization theory,” which held that individuals with extreme political opinions tended to look for like-minded people and eventually take violent action.

Many American Muslims believe the government uses sting operations to unfairly target their communities and that radicalization theory contributes to Islamophobia. “When people assume that one of their community members could be an informant for the government, that creates a ripple effect,” Kayse Jama, a Somali-American organizer who works in Portland, told BuzzFeed News. “They can’t trust the people at their mosque. They can’t trust anyone. They feel they can’t speak freely.” Studies suggest that at least some of Jama’s fears are well-founded.

Federal courts convict nearly 90% of those of accused of terrorism, most of them through guilty pleas. This means the facts of most homegrown terrorism cases are rarely entered into the public record, which in turn means the FBI is almost never forced to argue the legality of its techniques. Mohamud’s case is one of few exceptions.

Mohamed Osman Mohamud was born on Aug. 11, 1991, in Mogadishu, Somalia. Months earlier, rebels had ousted the country’s long-standing dictator, unleashing a civil war that rages to this day. On the way to the hospital, Mohamud’s parents had to confront armed thugs. They were lucky to find a doctor who helped with the baby’s breech birth.

The family fled to America. Mohamud’s father, Osman Mohamud Barre, went first, quitting his engineering professorship at Somali National University. Mohamud stayed behind, spending a year in a Kenyan refugee camp with his mother, Mariam Hassan.

The U.S. granted Barre refugee status. He settled in Hillsboro, Oregon, where he worked 13 hours a day at an Intel assembly line. By 1993, he had saved enough money to bring his family to the U.S. “They were malnourished and suffering, but they were happy,” Barre later testified at his son’s trial. “We were grateful to America.”

Barre climbed the ranks at Intel. He and Mariam had two more children. They moved to Beaverton, a prosperous suburb in southwest Portland. Mohamud devoured the Harry Potter series and became an NBA fan. He did well in school and made friends easily. “You would never see him alone,” Joshua Alinger, who befriended Mohamud in elementary school, told BuzzFeed News.

Early in high school, Mohamud became interested in religion, even as his parents became less observant. Several of his friends said many Muslim families in Beaverton felt that Mohamud exerted a positive influence. “Whenever we tried to do something that went against our religion, like date a girl, [Mohamud] was like a stopping point,” Mohamud’s best friend, who is not identified in the public record and who spoke on condition of anonymity, told BuzzFeed News. “He would just give us that look.”

Mohamud also joined in the hijinks of American adolescence. By junior year, he began skipping school. His best friend said the two of them would sneak out to a nearby community college to play pool. They made friends with an older student, who bought them alcohol and let them hang at his house. “I think he wanted to be a normal suburban teenager,” said James Duncan, an English teacher at Westville High School who oversaw Mohamud’s study hall.

Like many refugee children, Mohamud had to deal with cultural barriers that separated him from his parents, his American friends, and his mostly white classmates. There is little question he felt different. For an issue of the class magazine, for example, Duncan asked his students to draw cartoons of themselves and caption them. Under his portrait, Mohamud wrote, “I’m the black one.”

Around the same time, Mariam and Barre began to go through a breakup, Mohamud’s best friend said. “Home was kind of a hostile environment for him,” the friend said. “He tried to spend as much time as possible out of the house.”

(Reached at her home in suburban Portland, Mohamud’s mother declined to comment, saying her son’s attorneys had instructed her not to speak to reporters. “But one day,” she said, “I’ll be able to speak out about his case, inshallah” — God willing. Mohamud’s father did not respond to requests for comment.)

Mariam Barre at her son’s trial. Rick Bowmer / AP Photo

As his parents’ relationship deteriorated, Mohamud began spending more and more time at the Masjed As-Saber, a local mosque led by a Somali imam named Mohamed Kariye. The cleric had a complicated history. According to an immigration complaint, he spent part of his youth fighting with the Afghan mujahideen, a jihadi organization that counted Osama bin Laden among its supporters. (At the time, however, the U.S. supported the group in its fight against the Soviet Union.) In 2003, the FBI’s counterterrorism unit arrested him and charged him with Social Security fraud. (The imam pleaded guilty and paid roughly $5,000 in fines.) Today, the government is trying to take away the imam’s American citizenship.

Kariye’s teaching — Wahhabism, a traditionalist Sunni practice — proved too restrictive for some members of Portland’s Muslim community. The family of Mohamud’s best friend, for example, used to attend Friday prayers at the Masjed As-Saber, but eventually switched to another congregation. Mohamud’s parents, too, were “totally against the mosque,” his best friend said. For the teenager, frequenting the masjed became a form of rebellion.

At Kariye’s mosque, Mohamud met Amro al-Ali, an 18-year-old exchange student from Saudi Arabia. According to Marc Sageman, a former CIA officer who testified on “open source information” at Mohamud’s trial, the Saudi was “a wannabe” who liked to talk big about jihad but was, at least at that point, “not a terrorist.”

After meeting al-Ali, Mohamud began frequenting extremist websites, where he answered a call for submissions to an English-language webzine called Jihadi Recollections. The publication was the brainchild of Samir Khan, a Pakistani-American editor based in North Carolina. Khan commissioned him to write an article on fitness training, marking the beginning of a six-month-long collaboration.

But then, on Aug. 15, 2009, four days after his 18th birthday, Mohamud cut off contact with Khan. He wrote to Khan saying he was “going through a lot of things.”

(Shortly after Mohamud’s last email, Khan traveled to Yemen, where he became the editor of Inspire, the English-language outlet of al-Qaeda in the Arabian Peninsula. The U.S. government killed him in 2011, in the same drone strike that killed Anwar al-Awlaki, a top al-Qaeda figure and a U.S. citizen.)

Mohamud was indeed going through a lot — his parents had finally divorced. “You could see his discontent, sadness, and unhappiness,” the teen’s grandmother told his defense team. “He wouldn’t listen to either one of them because there was no union. He definitely tried to talk them into staying together many, many times.”

It was in that context that Mohamud received the email that sealed his fate. On Aug. 31, 2009, al-Ali sent him information about a religious school in Yemen. The thought of escaping to a distant land, away from his parents, appears to have seduced the teen. He stormed out of his mother’s house and called his father to say he was moving to the Middle East. Barre tried to convince him to wait, but Mohamud said he already had a ticket and a visa. Barre called Mariam and asked her to look for their son’s passport. It was missing.

Barre panicked. He had heard stories about kids from Minnesota’s Somali-American community who’d been “brainwashed” into joining the civil war. He remembered one news report of a teen who fled — the parents later found a photo of him on the internet “shot in the head, dead, in Somalia.”

Not knowing who to call, Barre contacted the FBI. “Can you guys help me to stop my son and make him not leave the country?” he asked the agent who picked up the phone. The agent took down Mohamud’s full name, date of birth, and address and told Barre to meet one of his colleagues at the parking lot of a local high school.

Meanwhile, Mariam found her son. He was in a playground not far from her house. She took his passport and drove him back home.

Mohamed Mohamud is seen in this undated handout photo. Obtained by BuzzFeed News

That afternoon, Barre met with FBI Special Agent Isaac DeLong, of the Joint Terrorism Task Force. “Why terrorism?” Barre asked. “Are you alluding that we are Muslim and my son’s name is Mohamed? There’s no terrorism here. We’re citizens.”

Barre explained that he wanted to keep his son from returning to Somalia. DeLong replied that there was nothing the bureau could do, because Mohamud was an adult.

That evening, the father and son had a difficult conversation. “I left my country because of violence,” Barre told Mohamud. “I brought you here to give you a life of prosperity.” Mohamud told his father had nothing to hide: al-Ali, a friend from the mosque, had recommended a school in Yemen. “You can learn Arabic and Islam once you finish school here and become mature enough to know wrong or right,” Barre replied.

Barre forwarded al-Ali’s email to the FBI, with a note saying he had spoken to Mohamud and the situation was under control. Unbeknownst to him, DeLong ran Mohamud’s email address through what he described at trial as “an FBI database.” The search, according to court records, turned out an interesting result: Mohamud had been in touch with the subject of another investigation — Samir Khan.

“I took this information to my superior,” DeLong testified. “We decided to open a case.”

The Bush administration’s warrantless surveillance operations remained secret until December 2005, when the New York Times published an exposé. The article unleashed outrage that pushed the president to seek retroactive legislative approval for the program. In July 2008, the Senate approved the FISA Amendments Act, or FAA.

The new law overwrote many of FISA’s provisions, empowering the attorney general and the director of national intelligence to authorize surveillance of people “reasonably believed to be located outside the United States.” Those offices no longer had to get warrants, as the original law mandated. Instead, they simply had to present the FISA court with a set of general procedures meant to “minimize” the “incidental” surveillance of people in the U.S.

On the same day President Bush signed the FAA, the ACLU filed a suit saying the law violated the First and Fourth Amendments. “The act does not require the government to demonstrate that its surveillance targets are foreign agents,” the ACLU wrote in its complaint. “The statute does not require the government to identify its surveillance targets at all.”

The suit, Amnesty v. Clapper, reached the Supreme Court. In February 2013, however, Justice Samuel Alito delivered an opinion declining to hear the case. He said the only people with standing to challenge the act were criminal defendants who, unlike the ACLU, knew for certain that their communications had been intercepted. (At that time, the government had not informed a single defendant of its use of the FAA.)

Then, in May 2013, Edward Snowden handed a group of journalists a cache of classified documents. The leaks detailed how the NSA invokes the FAA to intercept, store, and in some cases review the telephone and internet communications of hundreds of millions of people — many of them citizens and residents of the U.S.

It’s unclear to what extent domestic law enforcement agencies have access to the immense databases of information obtained through warrantless surveillance. In the past, the government has said FBI agents assigned to criminal investigations cannot see the data.

Marc Aspinall for BuzzFeed News

Early in September 2009, Mohamud moved to Corvallis, a small city a few hours south of Portland, to attend classes at Oregon State University. It was too late to enroll officially, so he couldn’t live in the dorms. His parents agreed to give him $300 a month for rent. Mohamud’s best friend, however, had just started at OSU, where he shared a large dorm room with two other students. Since they had an extra bed, they invited Mohamud to live with them for free. In exchange, “we called his rent budget our booze budget,” the friend said.

FBI documents described Mohamud as a “confused college kid that talks mildly radical jihad out one ear, and drugs, sex, drinking out the other.”

The group soon expanded to include two young men, Raed and Mohamed. Two of Mohamud’s roommates were dating a pair of best friends, and the dorm became the center of a tight-knit social scene. (The other roommates and the women declined requests for comment.) “Our freshman year was a drunken mess,” Mohamud’s best friend said. “It was a blast.”

Mohamud’s friends from that time acknowledged he was easy to influence. “He’d say, ‘I don’t want to drink anymore,’ but he could be persuaded to do it,” said Raed. “Like, a friend of mine would be like, ‘No, come on, let’s just drink for one more week,’ and he’d say, ‘OK, let’s go.’”

The FBI, which trial testimony shows was already reading Mohamud’s communications and had agents physically following him, agreed with Raed’s assessment. (The bureau refuses to disclose when, exactly, the surveillance began.) In emails sent to other FBI agents in the fall of 2009, Special Agent DeLong wrote that the “manipulable” and “conflicted” teen appeared to have “left behind his radical thinking.” Christopher Henderson, the special agent who took over the case when Mohamud moved to Corvallis, described the teen in internal emails as “a confused college kid that talks mildly radical jihad out one ear, and typical 18-year-old college kid (drugs, sex, drinking) out the other.”

Mohamed Mohamud is seen in this undated handout photo. Obtained by BuzzFeed News

Then, on Halloween, Mohamud and his crew headed to a fraternity party. Mohamud “was drinking like a normal person, dancing with girls,” and brought a woman home, Raed said. At the dorm, Raed said, they began having sex “in front of everybody, on the top bunk.” The friends eventually left the room.

The following morning, two Oregon State Police officers were in the dorm. The cops said that a young woman had filed a crime report accusing Mohamud of drugging and raping her.

Mohamud met with Detective Eli Chambers at the campus police office for a polygraph test. He denied having drugged the woman, but admitted that she was very drunk — “more drunk than I thought,” Mohamud said, according to Chambers’ report.

Chambers closed his investigation without pressing charges against Mohamud. Still, the incident rattled the student. After the polygraph, he wrote a long post in one of the forums he frequented:

I swear by Allah I have become so lost. And I want so badly to be in a muslim land. I keep telling myself that if I lived in a muslim land I would become so pious. […] Being in University and living on campus hasn’t helped me too much either. I have fallen into so many things (i.e. alcohol and women). […] All I need is some soft words to help my heart and supporting advice.

Instead of soft words, Mohamud began receiving emails from Bill Smith, a recent convert to Islam who lived in eastern Idaho and wanted to “get more involved in the fight” against enemies of the Prophet. Smith, however, was a fictional character created by FBI Special Agent Jason Dodd of the Portland field office.

(There were a number of oddities in Dodd’s decision to begin an operation against Mohamud. At trial, the agent testified that Special Agent DeLong authorized the “Bill Smith” emails, but DeLong could not recall such thing. Special Agent Elvis Chan, who would eventually run the operation that resulted in Mohamud’s conviction, testified that he did not know about the “Bill Smith” emails until after the arrest.)

On Nov. 12, 2009, just days after a Muslim U.S. Army major killed 13 people at the military base in Fort Hood, Bill Smith t0ld Mohamud that he had seen news reports of “brothers trying to fight.” “I want to, as well,” Smith wrote in one of about two dozen emails. “What can I do? Do you know who I can talk to? Can you help?” Mohamud did not engage him, cautioning him instead to be careful about what he said on the internet.

But then, on Dec. 3, 2009, someone familiar reached out to Mohamud. “Salamz bro,” the message read. “It’s me, Amro.” Al-Ali said he was making a pilgrimage to the holy city of Mecca, in Saudi Arabia. If Mohamud wanted to join, he said, a “bro” would contact him “about the proper paperwork.”

The FBI agents traced al-Ali’s computer not to Mecca, but to the northwestern border of Pakistan, one of the centers of violent jihad. The agents became convinced that al-Ali was writing in code, trying to recruit Mohamud as a fighter. Two months earlier, Interpol had issued an Arabic-language “red notice” — a sort of international “wanted” poster — saying al-Ali was “known to be connected to a fugitive wanted by Saudi Arabian authorities who is an expert in manufacturing explosives and in facilitating the movement of extremists inside Saudi Arabia,” according to a translation included in a defense brief. “He also helped al-Qaeda division in Yemen and other countries by providing them with foreign fighters to carry out terrorist attacks against western and tourist interests.”

(Later, the defense and the prosecution had heated arguments about the notice, which was ambiguous in Arabic and became vaguer in translation. Was al-Ali a member of al-Qaeda, or merely associated with a member? The matter was further complicated when the Saudis captured al-Ali, holding him without charges and subjecting him to repeated interrogations. A former intelligence officer told BuzzFeed News that classified reports detailing those interrogations show that al-Ali didn’t remember Mohamud.)

Mohamud responded that joining the pilgrimage would be “wonderful.” Al-Ali sent him a Gmail username and password, with instructions to log in to the account and draft, but not send, a message for a brother called Abdul Hadi. The FBI went on high alert, but Mohamud couldn’t figure out the system. No messages were exchanged.

Toward the end of spring semester, one of Mohamud’s roommates invited him to spend the summer working on a fishing boat in Alaska. Mohamud’s parents thought it would help discipline their son. They bought him a plane ticket and, on June 14, 2010, drove him to Portland International Airport.

The family made it only to the security checkpoint, where an airline employee told Mohamud he couldn’t board. As the family stood at the concourse, a man in a dark suit introduced himself as Special Agent Bradford Petrie. “I understand Mohamed was not allowed to fly today,” Petrie told the family. “We’d like to talk about that if we could.”

Marc Aspinall for BuzzFeed News

A week earlier, the FBI had decided to launch a full-scale undercover operation against Mohamud. Miltiadis Trousas, an agent based in the FBI office in Eugene, Oregon, wrote to Special Agent Chan, a sting specialist based in San Francisco, to suggest targeting the teen “using everything we have on him,” including the fact that he was “shy around authority figures.” When the agents learned of Mohamud’s plans to travel to Alaska, they worried he might try to continue to Pakistan or Yemen. They placed him on the no-fly list.

At the Portland airport, Petrie brought Mohamud and his parents to a conference room. Barre asked whether his call to the FBI a year earlier had anything to do with his son’s placement on the no-fly list. Mohamud denied visiting extremist websites. Petrie concluded the interview promising the family he’d try to “help” the teenager. He said nothing about the operation.

A few days after the interview at the airport, Chan contacted an FBI agent in California and asked him to fly to Portland to play an “al-Qaeda spotter” in a sting against a suspected teenage radical. The agent, who had been born and raised in an Arabic country, assumed the name Youssef.

Youssef got in touch with Mohamud nine days after the airport incident. The goal was to set up an in-person meeting, purportedly to assess whether the teen was serious about wanting to join a militant organization. The agent wrote in the voice of the “brother” whom al-Ali had earlier told Mohamud to contact, and whom the teenager never reached out to. “Salamz, bro,” the message began. “Go to hushmail.com and set up an account.” Mohamud replied with an innocuous greeting from an encrypted account. Two days later, Youssef wrote back: “Are you still able to help the brothers?”

Mohamud wrote back something noncommittal. Youssef’s next email suggested that God’s plan for Mohamud was in Portland: “Allah I’m sure has good reason for you to stay where you are,” the undercover agent wrote. He said he was traveling to Oregon and asked the teen to meet him in person.

Mohamud ignored the message. Worried about losing their target, the agents sent another. A week later, Mohamud responded by inviting Youssef to Friday services at the Masjed As-Saber. The FBI, however, did not want to send an undercover agent to a place of worship. Instead, the agent suggested meeting in downtown Portland. Mohamud grew suspicious. “How did you get my email?” the teen wrote. “And if Amro did give you my email, then how do you know him? And describe him to me if you really do know him.”

The FBI did not know what al-Ali looked like. To avoid blowing Youssef’s cover, the agents invented a fictional organization, which they called the “Ihata,” or Council. They told Mohamud that “a brother from Oregon” told the Council about him, prompting the group to send Youssef to interview him. Flattered, Mohamud agreed to meet on July 30, 2010.

For the first meeting, Youssef wore a suit to match his cover: a business traveler with connections across many countries. He met Mohamud on a street corner and walked with him to the Embassy Suites, a hotel blocks away from Pioneer Square.

The public record of that meeting is incomplete. In what the FBI claimed was an honest mistake, Youssef’s tape recorder had dead batteries. Apart from the anonymous agent’s testimony, the only source for what Mohamud said that day is a summarized report prepared by Chan. At trial, Chan said he had destroyed his original notes.

(The defense took great issue with this at trial. Entrapment law requires prosecutors to show that a defendant was predisposed to commit the crime before the first contact with government agents. The nuances of Mohamud’s behavior and language during the first meeting, the defense argued, were vital.)

In the FBI’s account of the meeting, Youssef and Mohamud sat at a table in a corner of the hotel lobby. The agent said the Council wanted to interview seven possible candidates in the U.S. and Canada.

“So, what have you been doing to be a good Muslim?” Youssef asked.

Mohamud said he’d written religious poems and a couple of articles for Jihadi Recollections.

“Well, you know, it’s pretty obvious that you can’t go overseas,” Youssef said. “So, what can you do for the cause? What do you want to do for the cause right now?”

Instead of answering with a concrete proposition, Mohamud told him about a dream in which he went to the mountains of Yemen, received training, and led a Muslim army against the infidels in Afghanistan. The undercover agent then repeated his question — what could the teen do for the cause? Mohamud said he could do “anything.”

“I gave him five examples of how you could be a good Muslim,” Youssef testified at trial. Mohamud, the agent said, could pray five times a day, train as a doctor and go overseas, donate money to the cause, become “operational,” or become “a martyr.”

Mohamud replied he wanted to become operational. Youssef asked what he meant. According to the FBI agent, the teen said he wanted to “get a car, fill it with explosives, park it near a target location, and detonate the vehicle.” Youssef told Mohamud he “had a brother that could help him with explosives” and instructed him “to research possible places within the Portland area as possible targets.” The two then parted ways.

The FBI brought a second undercover agent into the operation: a detective from a suburban police department in California assigned to his city’s Joint Terrorism Task Force. Like Youssef, the second agent was born and raised in an Arabic-speaking country. For the sake of the operation, he assumed the name Hussein. He prepared to play the role of a mature and deeply religious explosives expert.

Two weeks later, Mohamud met again with Youssef. The script for that meeting, the agent testified, was to “sell” the teen to Hussein, who was supposed to be initially skeptical. Youssef and Mohamud went to a room at the Embassy Suites, where Hussein was waiting — and where the FBI had installed several hidden cameras. They shared a meal to break the Ramadan fast.

“What can I do for you?” Hussein asked, according to his testimony.

Mohamud responded he wanted “a truck or a car and explosives.”

“I’d be glad to sell you a truck!” Hussein said.

“No,” Mohamud answered, “I want it for something else.”

The teen launched into a rant about the need to punish the U.S. for attacks against Muslims.

“You know what’s going on right now?” Mohamud said, according to a transcript of the recordings included in the prosecution’s trial memorandum. “The U.S. is losing the war. So they have resorted to intentionally killing civilians. And, you know, God, the glorified, the exalted, said in the Quran that if they kill your women and children intentionally, then you are allowed to do the same to them.”

The conversation shifted toward more concrete plans. Had Mohamud found a target in the Portland area, like Youssef requested?

“Do you guys know Pioneer Square?” the teen said. “When they have events, everybody comes up there. So, on the 26th of November, they have a Christmas tree lighting and some 25,000 people attend. You know, the streets are packed. I thought, I thought if you could help me, you know, to have, to have a truck. … You know, explosives, inshallah.”

“And this is what’s in your heart?” Youssef said. “You know, there’s going to be a lot of children there.”

“Yeah, I mean, that’s what I’m looking for,” Mohamud said.

“For kids?” Youssef asked.

“No, just for a huge mass,” Mohamud said. “You know, for them to be attacked in their own element, with their families, celebrating the holidays.”

Hussein asked Mohamud if he wanted to kill himself with the bomb.

The undercover FBI agent asked Mohamud if he wanted to kill himself with the bomb. “Yeah, I don’t mind that,” the teen said.

“Yeah, I don’t mind that,” the teenager said. He began to stutter. “That, that, that, I mean, if I wasn’t in it, then, you know, then, they’ll look for me.”

“And you are not worried?” Youssef asked.

“If you were going to paradise, you wouldn’t have to worry, right?” Mohamud answered. “Yes, I will push the button.”

“Allah is looking at you right now,” Youssef said.

“You know what I like, what makes me happy? You know what I like to see? When I see the enemy of Allah, and, you know, their bodies are torn everywhere,” Mohamud said.

Anticipating an entrapment defense and a jury of liberal Portlanders, the undercover agents made sure to give Mohamud a way out. “We want to make sure that it’s, you know, it’s in your heart,” Youssef told the teen. “If we get all the way there and you’re like, uh-oh — even if that happens, we’ll be disappointed, but you always have a choice, you understand? With us you always have a choice.”

On the drive home, Mohamud burst into tears. After he left the car, with the cameras still rolling, Hussein looked at his partner. “It’s almost too good to be true,” he said.

Pioneer Courthouse Square, the site of Mohamud’s attempted bombing, is seen on Nov. 27, 2010, in Portland, Oregon. Craig Mitchelldyer / Getty Images

Over the next few months, Youssef and Hussein met with Mohamud on five more occasions. They began giving him tasks. First, they sent him shopping for a timer, two cell phones, a toggle switch, and a snap connector. They asked him to find a few possible parking spots near Pioneer Square. Later, they told him to rent a storage shed where they could build the bomb.

More than anything else, they praised him: “You got a lot of talent, brother Mohamed.” “You’re probably smarter than most people.” “I think you can be a great poet.” “I trust you with my life.” “We love you, for the sake of Allah.”

As the operation progressed, the two agents grew concerned that Mohamud was becoming suicidal, so they decided to tell the teen that the Council would help him flee to a Muslim country after the attack. They were also worried that Mohamud would tell someone, so they gave him $2,700 to rent an off-campus apartment away from his friends. In a moment of telling naïveté, the teenager asked the two men he thought were al-Qaeda recruiters to sign as his guarantors for the lease.

The change in Mohamud’s lifestyle did not go unnoticed by his friends. He wouldn’t show up to class or parties. He stopped going to Friday prayers at the Corvallis mosque. “In the beginning, I didn’t really understand why he was drifting away,” Mohamed, one of the college friends, told BuzzFeed News. “And then Raed said, like, ‘Hey man, we feel like there’s something up. Like, he’s not the same anymore.’” On the few occasions when they saw him, he seemed anxious and in distress.

“One of my friends and I, we’d be walking to a party,” Raed said. “And Mohamed would be extremely drunk, and he would go to one of my friends and say, ‘Are you the FBI? Are you the FBI?’”

The night before the bombing, Mohamud had Thanksgiving dinner in Beaverton with a few friends. Afterward, they went shopping at a nearby mall. Several people who were there told BuzzFeed News that Mohamud seemed to be having a really good time. He insisted on buying coffee for everyone. He poured marshmallow liquor into his cup. He made jokes and laughed and acted like his old self, the way he used to be freshman year, before he moved out of the dorms and began spending all of his time alone.

“He told me, ‘I’m having the greatest morning of my life,’” Raed, who ran into Mohamud at 4 a.m. outside a J.C. Penney, told BuzzFeed News.

Later that day, Mohamud called his best friend to ask about his plans. The friend said he was going to see the Christmas tree lighting ceremony. Mohamud told him to stay home, but didn’t explain. The two have not spoken since.

Marc Aspinall for BuzzFeed News

Shortly after his arrest, Mohamud was appointed three lawyers from the Portland Federal Public Defender’s Office: Steve Sady, Steve Wax, and Lisa Hay. According to attorneys from around the country, the three were among the best terrorism lawyers in the U.S. All three declined to comment.

Mohamud’s trial began on Jan. 10, 2013, more than two years after the arrest. In her opening statement, Assistant U.S. Attorney Pamala Holsinger called Mohamud a “prolific user” of extremist websites, saying he was “well known” for his work for Samir Khan.

Holsinger said the government had contacted Mohamud because a “known terrorist” was trying to recruit him. She said the government would prove Mohamud’s attempt to travel to Alaska was a step toward his ultimate destination: Yemen. The prosecutor concluded by emphasizing the best evidence against Mohamud: “The defendant dialed this phone. And when the phone didn’t go off, he dialed it again.”

Sady, in his opening statement, accused the FBI of using “flattery” to get a manipulable teenager to do their bidding, invoking God and appealing to his fragile ego to make him do “the little things and big things that ended up bringing evidence into court today.” The federal defender told the jury he understood the difficulty of putting aside emotion to acquit a person who thought he was carrying out a heinous act. He implored jurors to evaluate the case based on law rather than hypothetical destruction.

“We all want law enforcement to stop crime​,” Mohamud’s defense lawyer said.​ ​“But the FBI cannot create the very crime they intend to stop.”

“In America, we don’t create crime. The entrapment defense is how this fundamental American value is made real in the courts,” Sady said. “It’s a line the government cannot cross. We all want law enforcement to stop crime. But the FBI cannot create the very crime they intend to stop.”

The government’s case was a rare look into an FBI undercover investigation — warts and all. Over nine days, 14 agents took the stand. Several were forced to confront off-color comments caught on tape during surveillance. During his cross-examination, Special Agent Mario Galindo — who had just explained to the jury that the reason the first face-to-face meeting was not recorded was because he accidentally left the recorder powered on the night before the operation — was asked to confirm a sexually suggestive comment he made after Mohamud first met the bomb expert, Hussein.

Sady: Did you express a feeling of enthusiasm by using a metaphor for sexual excitement?

Galindo: Which one?

Sady: Did you say, “You’ve got a lot of people with woodies up here right now?”

Galindo: Yes, I said that.

Both undercover agents testified for days. At one point, Lisa Hay grilled Youssef:

Hay: Did Mohamud say what kind of truck?

Youssef: He did not.

Hay: So the FBI decided what kind of truck, didn’t they?

Youssef: Yes.

Hay: The FBI decided the size of the bomb?

Youssef: Yes.

Hay: The FBI designed the bomb?

Youssef: Yes.

Mohamud didn’t testify in his own defense, though both his parents did. Barre told the court that he wished he had read his son’s text messages to see what was going on with him. Then, during cross-examination by prosecutor Ethan Knight, the distraught father attacked the actions of the FBI:

Knight: You were concerned, and that’s why you went to the FBI?

Barre: I went to the FBI to get help to stop him not to leave the country.

Knight: Because you were concerned that he might be brainwashed, isn’t that right?

Barre: That is what I was afraid of. But can I tell you, the FBI brainwashed my son.

Several of Mohamud’s friends took the stand on his behalf, calling him “goofy” and “fun-loving.” Raed, however, was subpoenaed to testify for the prosecution. He wasn’t happy about it and found a small way to rebel.

“The prosecution, they were like, ‘Make sure you look at the jury and you talk to them eye to eye,’” Raed told BuzzFeed News. “But I’m like, no. If I were here on the defense side, sure, I can be talking straight to the jury. But I’m here because I’m forced to. So I’m going to answer your questions and go on with my day.”

“I did look at Mohamed,” Raed went on. “We did make eye contact. He was crying.”

The trial closed after 14 days. Knight gave the government’s summation. He reminded the jury that Mohamud had believed the bomb was real. The case, Knight argued, was about “a choice, a single and remarkable choice by this defendant to take the lives of thousands of people.”

“An individual simply cannot be entrapped to commit an offense such as this,” Knight said. “This is the type of offense that one commits only because one wholeheartedly wants to.”

Steven T. Wax, left, and Stephen R. Sady, right. Rick Bowmer / AP Photo

Sady, the defense lawyer, gave an impassioned closing argument, citing Aleksandr Solzhenitsyn, the Soviet novelist who was forced into exile after publishing The Gulag Archipelago. “Solzhenitsyn says, ‘There is a line between good and evil that runs through the hearts of all people,’” Sady said. “The government shouldn’t be pushing that line.”

After seven hours of deliberations, the jury returned a guilty verdict.

Nine months later, Mohamud was sentenced. The government asked that Mohamud be given 40 years in prison, while his defense team pleaded for 10 years. Judge Garr King sentenced Mohamud to 30, citing a case of “imperfect entrapment” carried out by the government.

“Now, the jury found that defendant was not entrapped, but imperfect entrapment is available as a defense,” King said from the bench. “And in this case, it weighs slightly in favor of defendant in this case. The court realizes the agents often reminded the defendant he could back out of the plan if he had a change of heart, but that is balanced by the government’s inducement through the agent’s use of praise and religious references.”

Marc Aspinall for BuzzFeed News

Just over a month after Mohamud’s conviction, the Supreme Court published its decision not to hear the ACLU lawsuit challenging the constitutionality of the FISA Amendments Act, or FAA. As a criminal defendant who had been charged using evidence obtained through warrantless surveillance, Mohamud was one of the people who the court believed had standing to sue in place of the ACLU. The government, however, did not notify him of the surveillance until nearly a year after his conviction.

Sady and his team furiously litigated the issue. They filed a motion asking the court to force the government to disclose what it had learned about Mohamud using FAA warrantless surveillance. Although the attorneys were careful not to single out particular pieces of evidence for scrutiny, their motion hinted at many possible questions. Did the FBI database that Special Agent DeLong searched when he found out that Mohamud corresponded with Khan include electronic data swept up by FAA laws? What about other types of FAA surveillance that had become publicly known since the Snowden disclosures? Were those surveillance methods used against Mohamud? Could Mohamud be sure he hadn’t been targeted in a myriad of ways, some of them potentially unconstitutional?

For Mohamud, those questions meant the difference between prison and a new trial. Under a legal doctrine known as “the fruit of the poisonous tree,” courts must suppress any evidence that has roots in illegal government conduct, even if a warrant is later issued to legally obtain the same evidence. If it turns out that unconstitutional surveillance first led the FBI to Mohamud, the prosecution’s entire case could collapse.

Judge King, however, denied Mohamud’s request for more information about the FBI’s tactics, saying he would review the legality of the surveillance in private meetings with prosecutors.

Mohamud’s attorneys resorted to broader legal arguments. Much like the ACLU, they claimed the FAA provided “none of the protections that the First and Fourth Amendments require to limit governmental intrusions on privacy.” A vein of frustration ran through the pleadings, with the defense acknowledging at one point that it sought “suppression of unknown evidence […] gathered at unknown times by unknown means by unknown persons and agencies operating under unknown protocols.”

The government responded that the warrantless surveillance in the case did not originally target Mohamud, but rather unspecified foreigners living abroad “who generally are not protected by the Fourth Amendment.” The fact that communications belonging to American citizens living within the borders of their own country — such as Khan and Mohamud — might have been “incidentally” acquired under the authority of the FAA did not “render the collection unreasonable.”

Again, Judge King sided with the prosecution, denying Mohamud’s request for a new trial. (King declined a request for an interview.)

On Sep. 4, 2015, Mohamud’s attorneys filed a brief asking the 9th Circuit of the Court of Appeals to overturn King’s decision. The government has until December to file its response. Oral arguments could happen as soon as January 2016. Regardless of the outcome, the losing party is likely to appeal the matter before the Supreme Court.

A victory for the defense could end a significant chapter in the history of American law enforcement. It would follow other incremental decisions — including June’s passing of the USA Freedom Act, which curbed an NSA program that collected most Americans’ phone records — that have begun to roll back the emergency policies enacted in the tense days after Sept. 11. Crucially, it wouldn’t just end particular programs, but establish a principle that will guide how courts must balance individual rights against collective security.

By contrast, a victory for the prosecution would not just keep Mohamud in prison, but also continue the preventive approach to law enforcement that has developed since Sept. 11.

“The history of the criminal justice system demonstrates that infringements on rights begin in cases against a particular targeted group that does not have any public support,” Joshua Dratel, a defense attorney who has represented many American Muslims accused of terrorism, told BuzzFeed News. “However, over time those methods that get approved in those cases contaminate ordinary cases against ordinary persons, and especially against those who have politically unpopular opinions.”

On a recent autumn evening, Raed and Mohamed met at a bar in Corvallis to share memories about their friend, the convicted terrorist. The two hadn’t talked about Mohamud for a while, in part because things had been rough around campus after he got arrested.

“I mean, my name is Mohamed,” Mohamed told BuzzFeed News. “A lot of racist things have happened to me, many times, even before the incident. Afterwards, when I was on campus and people knew I knew Mohamed or hung out with him, they’d say things like, ‘Oh, Mo, you fucking terrorist!’”

“It’s sad, you know,” Raed said, as he flipped through Facebook photos showing himself and his friends at an anti-jihad rally. “For us to have to show up and be like, ‘No, this isn’t really us.’”

Would they want to see him again? The friends said nothing for a long time. Eventually, Mohamed broke the silence.

“The only reason I’d want to see him again would be to sit down with him, just like this,” he said, making a sweeping gesture over the table. “Because I’m curious. I want to figure out why. I want to say to him, ‘Some of your friends were [at Pioneer Square]. Why did you want to do it to them?’ Not ‘Why did you want to do it to everybody?’ Because he, at that time, obviously did not care about everybody. But he had such a close relationship with so many people who were there or could have been there. Why would he specifically want to do that to them?”

Raed then mentioned that Mohamud had written him a few times from prison. “They’re, like, normal conversations,” he said of the letters. “Like we’re talking like friends. He’s asking how am I doing, how’s my family doing, how’re our friends doing.”

Raed never wrote back.




























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