Case 324: Khalil Rayyan

*** Content warnings: Terrorism, gun violence *** In late 2015, a young pizza delivery man named Khalil Abu Rayyan from Dearborn Heights, Michigan, met and fell in love with a woman he met online. Jannah Bride had approached Khalil via the social media platform Twitter, and the two soon became close. Over the course of several months, Khalil would start admitting disturbing things to Jannah – fantasies he had about harming others. But nothing in the relationship was as it seemed… --- Narration – Anonymous Host https://www.instagram.com/caseys.snaps/ Research & writing – Erin Munro Creative direction – Milly Raso Production & music – Mike Migas http://mikemigas.com/ Audio editing – Anthony Telfer Sign up for Casefile Premium: Apple Premium https://podcasts.apple.com/us/podcast/casefile-true-crime/id998568017?ign-itscg=30200S&ign-itsct=casefile_podcastsSpotify Premium https://spotifyanchor-web.app.link/e/9gSwcv7USsbPatreon https://www.patreon.com/casefileFor all credits and sources, please visit https://casefilepodcast.com/case-324-khalil-rayyan Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

• 0:00Speaker 00

  From journalist Olivia LaVoix, the creator of the hit investigative series The Bakersfield Three, comes the new Case File Presents series, Ada. In 2011, the body of a woman was discovered in a California vineyard. For more than a decade, she was known only as Jane Doe. Then detectives finally discovered her name. But identifying her was only the beginning. Listen to Ada wherever you get your podcasts.

• 0:34Speaker 01

  Soft, cushy, plush, cozy. Soft, smooth, buttery, marshmallow-y, warm. Soft. Socks, underwear, tees and more. Bombas. Everyday comfort worth obsessing over. Visit bombas.com/audio and use code AUDIO for 20% off your first purchase. That's B-O-M-B-A-S dot com slash AUDIO. One purchase equals one donated, always.

• 1:06Speaker 02

  At Lowe's, this Veterans Day and every day, military members, veterans and their spouses get automatic MyLowe's Rewards Silver Status Benefits. Plus, 10% off eligible purchases with no annual limit. It's one way we honour and give back to those who have served and still do. Learn more and verify now at lowes.com/military. 10% discount can't be combined with another offer. Exclusions, terms and conditions apply. Loyalty program subject to terms and conditions. Details at lowes.com/terms. Subject to change.

• 1:50Speaker 00

  Our episodes deal with serious and often distressing incidents. If you feel at any time you need support, please contact your local crisis centre. For suggested phone numbers for confidential support and for a more detailed list of content warnings, please see the show notes for this episode on your app or on our website. This episode was originally released on Casefile's Patreon, Apple Premium, and Spotify Premium feeds as an early bonus for our paid subscribers. To receive these episodes early and ad-free, you can support Casefile on your preferred platform.

• 2:35Speaker 00

  One day in December 2015, a 21-year-old man from Michigan admitted something very disturbing to his girlfriend. Khalil Rayyan had met 19-year-old Jana Bride just a couple of months earlier via the social media platform Twitter. The two had bonded over shared interests and commonalities. Both were from strict Muslim families and lived in the city of Detroit. As they were unable to date openly, the way other young people in the United States typically would, their relationship had moved quickly, and they were already discussing marriage as a way to be together.

• 3:16Speaker 00

  Khalil and Jana would often talk about heavy topics, including violent crimes committed by the terrorist group Islamic State.

• 3:26Speaker 00

  During one such conversation in December 2015, Khalil made an alarming confession. He told Jana, quote: “I tried to shoot up a church one day. I don’t know the name of it, but it’s close to my job. It’s one of the biggest ones in Detroit. Yeah, I had it planned out. I bought a bunch of bullets. I practiced a lot with it. I practiced reloading and unloading. But my dad searched my car one day, and he found everything. He found the gun, and the bullets, and a mask I was going to wear.”

• 4:07Speaker 00

  Khalil said he'd decided to attack a church because it was an easy target. Lots of people would be in attendance and would be unarmed. Plus, it would make the news, he added. He had an AK-47 rifle, so he would be capable of shooting many victims. When Janaar asked Khalil if he would have shot women and children at the church as well as men, he responded: "I would have killed every last one of them. I would have shown no mercy."

• 5:06Speaker 00

  Khalil Rayyan was raised in the Detroit suburb of Dearborn Heights, which had a large Arab-American population. Many women in the area wore hijabs, a head covering wrapped over the hair and beneath the chin. Some men wore long, loose-fitting robes known as a "thobe", and the call to prayer could be heard echoing through parts of the suburb five times a day.

• 5:32Speaker 00

  Khalil was the son of Palestinian immigrants, though his parents split up when he was three. He was then primarily raised by his father's family, and he received plenty of love and care while at home.

• 5:47Speaker 00

  He had six younger siblings and step-siblings. But despite growing up in an Arab-American family and neighborhood, Khalil felt torn between two worlds. He also wanted to be an ordinary American kid, so he sometimes went by the nicknames Kay or Ray to sound less foreign.

• 6:10Speaker 00

  In September 2001, when Khalil was seven years old, the 9/11 attacks changed everything.

• 6:18Speaker 00

  They were committed by nineteen terrorists, all of whom were extremist Muslims affiliated with the jihadist group Al Qaeda, an armed militant organization dedicated to establishing fundamentalist Islamic states. Suddenly, some people in Khalil's community began looking at him differently. He was bullied at school for his heritage and began lying about his background, telling people he was Hispanic or Italian.

• 6:49Speaker 00

  Although he lived in a strong Arab-American community, in a broader sense, Khalil felt like an outsider.

• 6:58Speaker 00

  As he grew older, he became more troubled. At the age of twelve, he had a dream that he took a gun to school and shot his entire class. He later told a teacher about the nightmare, and he was referred to counselling.

• 7:15Speaker 00

  As a teenager, Khalil developed a reputation for being a class clown at the charter high school he attended, where the other students were also of mostly Muslim and Arab descent.

• 7:28Speaker 00

  But he also became the target of bullies and was given suspension on at least three separate occasions after getting into fights. While his home life was stable, Khalil struggled with his peers and with depression. By the age of seventeen, he'd started using cannabis.

• 7:50Speaker 00

  It was after graduating, however, that Khalil's problems escalated. He briefly attended college, but his poor mental health and drug use led to him failing his classes. He decided to essentially drop out and take a break from studying to work full-time as a pizza delivery driver.

• 8:11Speaker 00

  Khalil's father was an engineer with two master's degrees, and he also owned a pizzeria. Working for his father at the pizzeria seemed like a good solution. However, without the structure of school and the friends he'd previously seen daily, Khalil's depression worsened. His job was isolating, involving long hours alone in a car, sometimes up to seventy hours a week. Khalil became even more dependent on drugs, often smoking between deliveries to curb his boredom and a low mood. By the age of nineteen, he was often smoking between ten and fifteen cannabis joints a day.

• 8:57Speaker 00

  To make matters worse, Khalil often felt unsafe while working. Detroit could be a dangerous city, and Khalil was generally working late at night. He had to deliver pizza at sketchy-looking apartment buildings or on blocks with no porch lights to aid visibility. On more than one occasion, Khalil would pull up at an address to deliver a pizza, only to find it was an abandoned house and there were people waiting there to jump and rob him. Sometimes Khalil was even robbed at gunpoint.

• 9:37Speaker 00

  Feeling lonely, angry, and powerless, Khalil suffered something of an identity crisis, wondering who he was and where he belonged. He began spending his free time retreating online to seek out a sense of belonging with other young Muslims his age. Then he started seeking out shocking and graphic content as a distraction from his own feelings. Seeing real gore and violence just felt like an escalation from watching an action movie. It involved the same shock and awe on a heightened level. By this time, it was 2014, and the actions of the terrorist group Islamic State, or IS,

• 10:22Speaker 00

  had captured the world's attention.

• 10:26Speaker 00

  Militants from IS had taken over large territories in eastern Syria, where there was an ongoing civil war, and northwestern Iraq, where local military forces were dwindling.

• 10:39Speaker 00

  IS declared itself to be a caliphate, the term for a state under the leadership of a religious Muslim considered a successor to the Islamic prophet Muhammad.

• 10:51Speaker 00

  IS adheres to a radical, pro-Sunni Islamist ideology and seeks to establish a global caliphate through armed struggle. It was designated as a terrorist organization by the United States government in April 2014.

• 11:10Speaker 00

  As they conquered parts of Syria and Iraq, IS became known for their use of social media to disseminate their message. They posted news, photos, and videos on Twitter as a way to reach a broader audience beyond their geographical borders and radicalize sympathetic individuals abroad. IS also became known for their brutality. Much of the content they shared featured shocking acts of violence against those they deemed their enemies. One such video was of a Jordanian pilot they had captured being set on fire and burned to death.

• 11:51Speaker 00

  Others showed men who were suspected by IS of being gay being thrown off a high-rise building as a form of execution. IS also used public beheadings to terrorize and punish and filmed soldiers, journalists, aid workers, and others being killed this way. In one incident, a French citizen and mountaineering guide named Hervé Gourdeau was kidnapped in Algeria, then held hostage before being beheaded. This crime was filmed and released online under the title "A Message of Blood for French Government."

• 12:34Speaker 00

  Khalil Rayyan had a Twitter account using the handle @khalilray21.

• 12:42Speaker 00

  In November 2014, he started seeking out IS content. He liked propaganda posts about their victories, including videos of beheadings and the Jordanian pilots murder. Sometimes he would retweet posts resharing them on his own profile or reply with a comment.

• 13:05Speaker 00

  In one instance, he asked another Twitter user if they had a link to a video showing people being thrown from a tall building. When the other user shared it with him, Khalil replied: “Thanks, that made my day.”

• 13:21Speaker 00

  Khalil sent some photos of beheadings to his brother. He saved one such photo as the screensaver on his smartphone.

• 13:32Speaker 00

  Emboldened by the online world he was falling into, Khalil took a photograph of himself and two friends, all dressed in camouflage. Khalil was holding a semi-automatic pistol in his right hand. His left hand was pointing skyward, his index finger raised. This gesture was a commonly acknowledged sign of support for Islamic State, known as the Torheed, a term referring to the oneness of God. Neither of Khalil’s friends were making the gesture.

• 14:08Speaker 00

  On Thursday, February 19, 2015, Khalil shared this photograph on his Twitter account.

• 14:18Speaker 00

  Throughout 2015, Khalil continued to immerse himself in IS content after clocking off from work. Late in the year, he decided to buy a gun.

• 14:32Speaker 00

  On Monday, October 5, Khalil went to a Dearborn Heights sporting goods store and purchased a 22 caliber revolver.

• 14:41Speaker 00

  To complete the purchase, he had to fill out a form required by the Bureau of Alcohol, Tobacco and Firearms, commonly known as the ATF.

• 14:51Speaker 00

  Question 11E on the form asked: Are you an unlawful user of or addicted to marijuana or any depressant, stimulant, narcotic drug or any other controlled substance? Khalil checked no and signed the form. Two days later, Khalil left work and got into his 2001 Buick Sentry. As he was driving away from the pizzeria, he noticed two police cars with their lights on signalling him to pull over. Khalil did so at a nearby intersection.

• 15:30Speaker 00

  The officers approached him on foot with their weapons drawn, later saying that as they did so, they could see him still seated in his car, bending down and making hurried movements, as though hiding something. When the officers reached Khalil, they noticed a strong smell of cannabis and asked Khalil to exit the vehicle. As Khalil did so, he told the officers that his gun was in the car. The officers found it on the floor under the driver's seat. When Khalil asked the officers why they had pulled him over in the first place, one told him that he'd been speeding.

• 16:10Speaker 00

  Another pointed to some prayer beads Khalil had hanging from his rearview mirror and said they'd stopped him for obstruction of vision.

• 16:20Speaker 00

  Canine units were called in, and police also recovered a plastic bag under the dashboard which contained a black vial, three sleeping pills and four baggies of cannabis. In total, the search took about three hours. Khalil was arrested for possession of cannabis and for carrying a concealed weapon.

• 16:44Speaker 00

  Michigan was an open carry state, meaning residents were permitted to carry firearms provided they were displayed openly.

• 16:53Speaker 00

  To conceal carry, you needed a special licence. Khalil did not have this licence, and hiding a gun under his driver's seat counted as concealment.

• 17:07Speaker 00

  Khalil waived his Miranda rights and provided a full statement to the police, stating: "I tried to hide the gun under my seat because I panicked. I think my fidgeting made the police officer nervous because he ordered me out of the car. That's when I told him, 'Hey man, I got a pistol.'"

• 17:28Speaker 00

  Khalil Rayyan spent the night in jail and was released on bond the following morning.

• 17:37Speaker 00

  Khalil was charged with carrying a concealed weapon and illegal possession of a controlled substance one month later. At around the same time, on Sunday, November 15, he tried to buy another gun. He went to a different sporting goods store and again filled out the ATF form the same way. But this time, his purchase was blocked due to his pending court case.

• 18:05Speaker 00

  Later that day, Khalil and a friend went to a local firing range. The pair rented an AK-47 and an AR-15 rifle, both of which are military-style firearms. Background checks were not required for this. Khalil took photographs of himself holding the weapons, and two weeks later, he posted one of these pictures on Twitter.

• 18:33Speaker 00

  He captioned the photo "Sawat hunting."

• 18:37Speaker 00

  Sawat is an IS term for a person who opposes their group, originally referring to the Sunni tribesmen who fought alongside US-led coalition troops in Iraq.

• 18:52Speaker 00

  About one week after Ryan posted this photo, he received a direct message on Twitter from a 23-year-old woman called Gada. She'd noticed his account and was reaching out.

• 19:07Speaker 00

  Gada told Khalil she was of Pakistani descent and lived in Cleveland, Ohio.

• 19:14Speaker 00

  She shared some photos of herself with Khalil. Some were selfies she'd taken in front of a mirror, others were her with her family.

• 19:25Speaker 00

  Khalil thought she was beautiful. The pair exchanged phone numbers and soon they were texting each other daily.

• 19:35Speaker 00

  Khalil had never had a girlfriend before. Their relationship quickly escalated from getting to know one another by asking questions about their lives to a serious romance where they were discussing marriage.

• 19:50Speaker 00

  Khalil told Gada that his religious faith forbade him from playing games with her. If they were going to be together, it needed to be a commitment. Within a week of meeting, they were describing themselves as engaged.

• 20:08Speaker 00

  Although he was yet to meet Gada in person, her presence in Khalil's life had already made an enormous impact. In one message, he told her: "While I was driving, I started to cry because of how happy I am to have you."

• 20:26Speaker 00

  "Don't cry, my love, please," Gada replied. "It's tears of joy," Khalil reassured her. "I never felt this way before."

• 20:38Speaker 00

  The lovestruck young couple discussed what their wedding would be like and how many children they would have.

• 20:46Speaker 00

  Eager to progress to the next stage of their relationship, Khalil said he didn't want them to sneak around behind their family's backs. Instead, their parents should meet one another.

• 20:59Speaker 00

  He spoke about it with his father, who said he was happy to go to Ohio with Khalil to meet Gada and plan their wedding. Khalil went back to Gada to share the news, but wasn't met with the joy he expected.

• 21:16Speaker 00

  Instead, Gada said she was having second thoughts about everything and wasn't sure it was a good idea. She then stopped responding to Khalil altogether.

• 21:29Speaker 00

  He was heartbroken and distraught. Their relationship had ended as quickly as it began.

• 21:38Speaker 00

  Khalil wondered if he'd been too clingy or rushed to the situation.

• 21:44Speaker 00

  Whatever had gone wrong, he believed that must have been his fault.

• 21:57Speaker 00

  Case File will be back shortly. Thank you for supporting us by listening to this episode's sponsors. The holidays are always such a busy time of year, and between work, socialising and everything else going on, the last thing I want to be thinking about is what I'm going to make for dinner every night. With fresh ingredients delivered straight to your door and easy recipes to follow, Home Chef takes the stress out of dinner. There are more than 30 meals to choose from each week, with options for different tastes and dietary needs, including calorie-conscious and GLP-1-friendly meals. And there's something for every schedule, whether you want a 30-minute meal, an oven-ready

• 22:40Speaker 00

  tray, or a quick microwave lunch, Home Chef has you covered. Olivia LaVoix from the Case File Presents series The Bakersfield 3 says Home Chef is one of her go-to options when life gets busy. She loves that it's convenient, uses quality ingredients, and lets her try new meals without spending hours planning. So this holiday season, give yourself one less thing to think about. For a limited time, Home Chef is offering my listeners 50% ...off and free shipping for your first box plus free dessert for life. Go to homechef.com/casefile.

• 23:18Speaker 00

  That's homechef.com/casefile for 50% off your first box and free dessert for life. Homechef.com/casefile. Must be an active subscriber to receive free dessert.

• 23:36Speaker 03

  A rug shouldn't just fit your room. It should make your home feel finished. Ernesta creates designer quality rugs, custom fit to the exact size of your space, so every room feels beautifully pulled together. Explore Ernesta's range of options, all ready to be custom cut, finished, and delivered to your door in as little as two weeks. Start with five samples for just $10 and get $50 toward your rug when you order. Visit ernesta.com today. That's E R N E S T A dot com.

• 24:08Speaker 04

  Shipping, billing, admin, payroll, marketing. You're managing all the things, so why waste time sending important documents the old fashioned way? Mail and ship when you want, how you want with stamps.com. Print postage on demand 24/7 and schedule pickups from your office or home. Save up to 90% with automated rate shopping. That's why over 1 million small businesses trust stamps.com. Go to stamps.com and use code PODCAST to try stamps.com risk free for 60 days.

• 24:41Speaker 00

  Thank you for listening to this episode's ads. By supporting our sponsors, you support Casefile to continue to deliver quality content.

• 24:56Speaker 00

  A couple of weeks after Gada disappeared, Khalil received a direct message from another young woman on Twitter. Her name was Jana Bright and she was of Iraqi descent. At 19, she was a few years younger than Gada, and she also lived closer to Khalil. Like him, she was a Sunni Muslim residing in Detroit. Jana told Khalil that she felt an overwhelming urge to talk to him, and she believed God had connected them.

• 25:30Speaker 00

  Jana had suffered a lot recently and was deeply depressed. Like Khalil, she'd experienced heartbreak. She had been engaged to a young man named Ahmad who had died during an airstrike in Syria. Two of Jana's cousins had also been killed by anti-IAS forces. Now she was living at home with her parents, whom she felt were destroying her life. Jana was suicidal and needed somebody to talk to.

• 26:05Speaker 00

  Over the course of mid to late December 2015, Khalil and Jana began communicating daily. Khalil developed romantic feelings for Jana quickly, but she was slower to respond. Jana seemed too absorbed by her own pain to be interested in dating at all.

• 26:27Speaker 00

  Nevertheless, the two became close and were soon confiding intimate thoughts and feelings to one another. They found some common ground in their feelings about Islamic State. Jana was a staunch supporter of the group, as she blamed their enemies for the deaths of her fiance and cousins. Khalil began confessing some of his darker thoughts to Jana. He told her about a plan he'd had to shoot up a church near his home with an AK-47. He'd chosen it as a target because lots of people went there and he knew the parishioners would be unarmed.

• 27:08Speaker 00

  Khalil told Jana he would show no mercy, even killing women and children. "Honestly, I regret not doing it. If I can't go do jihad in the Middle East, I would do my jihad over here. Maybe down the line I can try again."

• 27:28Speaker 00

  Jihad is an Arabic word that translates to struggling. In an Islamic context, it can refer to an individual striving to live a moral life or to put efforts towards building a good Muslim community. However, in the context of extremist Islam, it has come to mean an armed struggle against perceived enemies of the religion. Jana understood where Khalil was coming from. She told him: "Jihad is my dream." She was suicidal, but only had interest in dying if she could murder herself for God and as revenge for the deaths of Syrians and Iraqis following international invasions.

• 28:14Speaker 00

  The following month, Khalil told Jana that hearing about shootings and murder excited him. "I would gladly behead people if I needed to," he said. "It is my dream to behead someone."

• 28:30Speaker 00

  He claimed that sometimes Satan spoke to him at night, telling him to burn people alive and cut their tongues. Khalil also wanted to murder one of the police officers who'd arrested him for concealed carry and possession of a controlled substance a few months earlier. Khalil explained that his trial had been delayed because the officer in question had suffered a heart attack and was in hospital. Khalil said he wanted to commit a "martyrdom operation" at the hospital, killing the officer in the process.

• 29:06Speaker 00

  Khalil also said he was now carrying a large knife or sword in his car in case he ever got into a fight.

• 29:14Speaker 00

  He told Jana that his father knew about Khalil's support of IS and that he'd told his father that he wanted to make jihad. Khalil's father did not support this and had warned his son to be careful about what he said and posted online.

• 29:36Speaker 00

  On Thursday, February 4, 2016, Khalil received a text message from Jana early in the morning. She asked whether he was going to work that day. Khalil replied that he was, then got ready for his shift. He left home and stopped to get gas before driving to work. Khalil was opening up the pizzeria that day, and as he approached the front door, he suddenly saw a man with an AR-style rifle aimed at him. He ordered Khalil to get on the ground. Soon, there was a swarm of other people surrounding him, all brandishing firearms and wearing bulletproof vests.

• 30:21Speaker 00

  They were agents for the Federal Bureau of Investigation, or FBI. As they placed Khalil under arrest and searched the pizzeria, a simultaneous raid was taking place at his family home. His mother and younger sister were escorted from the premises, while his younger brother was handcuffed.

• 30:43Speaker 00

  Khalil Rayyan was taken to the FBI headquarters and placed in an interrogation room. An agent informed him that he was under arrest for possession of a firearm by an unlawful user of a controlled substance. Khalil already knew he had state charges pending for these offences and wasn't aware they'd been upgraded to a federal level. He requested a lawyer several times, but the FBI agent told him he had some questions to ask first. "What is your involvement with Islamic State?", the agent asked. At that point, Khalil realised he was under investigation for terrorism.

• 31:26Speaker 00

  He responded by asking what he was being charged with.

• 31:31Speaker 00

  The agent repeated that it was just a gun case, but followed up by asking about posts Khalil had shared on social media and his thoughts about Islamic State. He then brought up Jana, implying that she was being questioned simultaneously in the room next door.

• 31:51Speaker 00

  The agent knew about things the two had discussed, like Khalil's plan to commit a mass shooting at a church and his desire to behead people.

• 32:01Speaker 00

  At that point, Khalil began to worry about Jana. If the FBI had evidence against them, he wanted to take the rap so she could go free.

• 32:13Speaker 00

  Despite the agent's questions, no additional charges were laid against Khalil, nor was he charged with anything relating to terrorism.

• 32:24Speaker 00

  But this time, he wasn't being released on bond. He was to be held in federal custody until his case was resolved.

• 32:34Speaker 00

  Almost two weeks later, on Tuesday, February 16, Khalil was charged in a two-count indictment. He was being charged with making a false statement to acquire a firearm for lying on the ATF form when purchasing his handgun by stating he wasn't an unlawful user of a controlled substance. He was also charged with possession of a firearm by a prohibited person.

• 33:02Speaker 00

  As Khalil sat in court, his attorney went through his charge sheet. After reading it, she turned to Khalil and told him that the woman he knew as his girlfriend, Jana Bride, didn't exist at all.

• 33:21Speaker 00

  It turned out that the FBI had been monitoring Khalil Rayyan ever since May 2015, after his Twitter account came to their attention. His comments and posts in favour of IS activities had been flagged, and a review found that he’d been liking and retweeting IS propaganda for over six months.

• 33:45Speaker 00

  The FBI began investigating Khalil via a number of methods, including monitoring of his social media accounts and surveillance.

• 33:55Speaker 00

  A few months after they first began surveilling Khalil, the FBI became aware that he’d bought a firearm.

• 34:03Speaker 00

  They arranged for local police to pull Khalil over just two days after the purchase, under the guise of a routine traffic stop. It was then that Khalil was first charged with criminal offences, for the concealed carry of the gun and possession of a controlled substance. The FBI has not released the full facts of their investigation into Khalil, but it is believed that they first attempted to approach him undercover about two months after his arrest, using the online persona of Gada.

• 34:37Speaker 00

  Gada initiated a whirlwind romance with Khalil via Twitter, and he had believed that they were engaged to be married. But then Gada abruptly entered the relationship, leaving Khalil feeling broken. A few days after Khalil last heard from Gada, either the same agent or another one reached out to Khalil again with a brand-new persona.

• 35:04Speaker 00

  Unlike Gada, Jana Bride’s approach was grounded in a strong focus on Islamic State. The agent operating as Jana gave her a history steeped in conflicts taking place in the Middle East, and repeatedly turned their conversations to the topics of jihad, martyrdom, and IS.

• 35:25Speaker 00

  During conversations throughout December 2015 and January 2016, Khalil made a number of statements that the FBI took as indications he might be planning a terror attack.

• 35:40Speaker 00

  These included claims that he'd previously planned to shoot up a church. Based on information in Khalil's messages, agents were able to identify a church that fit the description he gave. It was less than half a mile from the pizzeria where Khalil worked and stretched across two blocks. It was a large building with the capacity to fit 6,000 people.

• 36:08Speaker 00

  In late January 2016, Khalil also talked about wanting to go to the hospital where the officer who arrested him was being cared for and murdering him. The next day, he told Jana how he carried a sword in his car and added, “I would gladly behead people if I needed to.”

• 36:30Speaker 00

  About two weeks after this, on Thursday, February 4, FBI agents struck. They arrested Khalil at his workplace and confronted him with what they knew about his terrorist ambitions.

• 36:47Speaker 00

  In the days following Khalil Rayyan’s second arrest, articles were published about the incident in local and national newspapers and media outlets. Headlines announced that a 21-year-old man had been arrested on suspicion of supporting Islamic State and planning to attack a Detroit church. Khalil was portrayed as a dangerous budding terrorist who had been successfully stopped before he’d caused harm.

• 37:17Speaker 00

  The FBI's criminal complaint against Khalil was also shared online.

• 37:23Speaker 00

  The affidavit contained this notable quote from FBI Special Agent Alan Southard: “Since May of 2015, the FBI has been conducting an investigation of Khalil Abu Rayyan regarding increasingly violent threats he has made to others about committing acts of terror and martyrdom, including brutal acts against police officers, churchgoers, and others on behalf of the foreign terrorist organization Islamic State of Iraq and Levant.”

• 37:57Speaker 00

  Khalil was held on bond and had to undergo a competency exam to prove he was fit to stand trial. A grand jury indicted Khalil on the two gun-related felonies the FBI had initially charged him with: making a false statement to acquire a firearm and possession of a firearm by a prohibited person.

• 38:19Speaker 00

  However, the grand jury did not indict Khalil on any terrorism charges.

• 38:27Speaker 00

  On Tuesday, September 13, 2016, Khalil faced court. On the advice of his attorney, he pleaded guilty to the two federal firearm charges. He had already pleaded guilty to the state charges relating to the same offenses, and the evidence against him was clear.

• 38:48Speaker 00

  Khalil told the court of his deep remorse for his actions, stating: “I am so ashamed, I have humiliated myself. That conduct is not who I am or what I believe in. Islamic State has nothing to do with Islam. I have shamed my faith. I have shamed the Muslim people.”

• 39:11Speaker 00

  Sentencing guidelines for these charges typically called for 10 to 16 months in prison. The judge spoke for an hour before sentencing Khalil, focusing primarily on Khalil’s support for Islamic State. “This is not merely viewing an Islamic State website,” the judge stated, while pointing to the threats Khalil had shared with Jana. The judge also cited the photo Khalil had posted of himself to Twitter, holding a military-grade rifle and claiming he was sawat hunting. Although Khalil had expressed remorse for holding these sentiments, the judge said his apology was “too little, too late.”

• 39:54Speaker 00

  He sentenced Khalil Rayyan to five years in federal prison.

• 40:03Speaker 00

  Although the shocking headlines about Khalil’s planned terrorist attacks had scared some members of the public, there were others who harbored concerns about the case against the young man. Civil rights advocates and Muslim-American leaders believed Khalil’s case was emblematic of a larger abuse of power taking place.

• 40:25Speaker 00

  What hadn’t been included in the FBI’s criminal complaint against Khalil Rayyan was mitigating evidence that indicated he had never had any intention to commit a terrorist act at all. In fact, the evidence provided by the government was missing key portions of the conversations between Khalil and Jana, with nothing at all provided from before December 23, 2015, well into the pair’s relationship. The government claimed these omissions were due to a printing error, but Khalil’s defence team suspected otherwise. They filed a motion for discovery to gain access to the FBI’s full case against Khalil.

• 41:10Speaker 00

  The government was able to successfully withhold most of its surveillance evidence by arguing that doing so would protect national security. But a closer look at the conversations between Khalil and Jana that were available still provided greater clarity as to what had actually taken place.

• 41:30Speaker 00

  From the start, Jana Bride had presented as a deeply depressed, suicidal young woman who had suffered immense loss. While she had repeatedly raised the subject of Islamic State and jihad, Khalil’s responses to her had been more focused on building a romantic relationship. “I wish I could take you away from this sadness,” he wrote. “I pray a lot for your happiness. Sometimes I think I see you in my dreams.” Over time, he started professing his love to Jana and asked her to marry him. Lonely and depressed, Khalil had never had a romantic relationship before and saw marriage as a way to be happy.

• 42:17Speaker 00

  He tried to dissuade Jana from harming herself or others, telling her, “Just stay positive, everything will work out.” In one conversation, Jana expressed her deep sadness before asking Khalil, “What do you want from this dunya?”

• 42:37Speaker 00

  Dunya is an Arabic word referring to the temporal world. Khalil replied, “Honestly, to get married. I think if I get married, I will be happy. I’m just lonely sometimes. I want to start a family.”

• 42:55Speaker 00

  “What about the afterlife?” Jana asked, before adding, “I want to leave this dunya. I don’t want to get married.” Khalil encouraged her not to give up, reassuring her that her life would improve. “Don’t you want to have children and watch them grow up?” he asked. “That’s probably the best feeling.”

• 43:18Speaker 00

  In subsequent conversations, Jana spoke of wanting to murder herself for Allah or God, stating, “I want to die for the sake of Allah.” Her motivation for doing so was vengeance for, “Seeing my sisters and brothers and young women die in Syria and Iraq like that.” Khalil replied that she was young and confused and didn’t know what she wanted. “Jihad is my dream,” Jana responded.

• 43:52Speaker 00

  But Khalil didn’t pick up on these threads, instead trying to convince Jana that marriage and building a future was the best path forward. During one conversation, Jana appeared to directly ask Khalil about a possible plan for them to commit jihad together, writing: “So you don’t want to do anything of what we talked about together?”

• 44:18Speaker 00

  “No, I can’t,” Khalil replied. “I want us to be together. I have other plans. Don’t do anything that will hurt yourself or other people.”

• 44:32Speaker 00

  At one point, he grew so tired of Jana’s repeated talk about jihad that he stopped talking to her for three days. She continued to contact him incessantly during that time. Perhaps picking up on his distaste for conversations about violence, she no longer messaged about that, but instead said how much she needed someone to talk to. Khalil caved and resumed contact.

• 45:02Speaker 00

  This time, when Jana began fixating on Islamic State and jihad again, Khalil followed her lead. He would later explain in an interview with progressive advocacy group The Gravel Institute that he could see those were the things that were “turning her on”. So, he decided to go along with it to impress Jana and maintain her interest. Whenever he turned to other topics, Jana became distant and started to pull away. Desperate to keep her attention, Khalil started making up stories, claiming he’d been accused of murder and had spent three months in prison before being let go.

• 45:46Speaker 00

  This had never happened. Khalil said that his claims of wanting to behead people or commit a massacre at a church were invented as well, to make him sound more like the sort of man Jana would be interested in.

• 46:03Speaker 00

  When the FBI searched Khalil's home and workplace, they found no trace of the AK-47 he said he'd owned. The truth was that Khalil had never owned an AK-47, nor did he have any bullets. He had purchased a handgun in October 2015, but this was in response to feeling unsafe at work. After being robbed multiple times while delivering pizzas, sometimes at gunpoint, he felt he needed to be armed for protection.

• 46:36Speaker 00

  The gun he bought could only carry six bullets in its chamber. He'd had it for just two days when he was pulled over and it was confiscated by the police.

• 46:48Speaker 00

  Khalil had also told Jana he'd bought a mask to wear during the church attack, but no such mask was recovered during searches by the FBI.

• 46:59Speaker 00

  Khalil's defenders have described his proposed massacre as fantasy to impress a girl. But prosecutors argued that even if he hadn't made preparations to carry it out, his messages were still an expression of intent.

• 47:17Speaker 00

  The situation between Rayyan and Jana reached a boiling point in early February 2016. Rayyan had grown increasingly depressed while awaiting trial for the gun charges. He was also anxious because his phone had been searched following his arrest and he knew authorities might find the Islamic State content he had downloaded and watched. There were also photos of him posing with guns at the firing range. He worried these might lead to further charges.

• 47:51Speaker 00

  During a phone conversation on Tuesday, February 2, Rayyan told Jana that he was suicidal and had bought a rope to hang himself. "I'm tired of this," he said. "We're doing the same thing every day." He told Jana of his anxieties that he might be charged with further offences. He claimed he'd tried to travel to Syria a year earlier to join Islamic State, but had been turned away. Lately, he'd noticed that he seemed to be under surveillance.

• 48:26Speaker 00

  There were always cop cars near his workplace, or dark vehicles following him. One time, Khalil had actually called the police to report that he'd seen a man in a vehicle taking photos of him.

• 48:40Speaker 00

  An officer had attended the scene, spoken to the man in the vehicle, and then told Khalil that it was fine. The man had just been taking photos of some nearby signs.

• 48:53Speaker 00

  Jana pushed back against Rayyan's suicidal ideation, telling him that taking his own life was haram, forbidden by Islamic law. "When it's for the sake of Allah, when it's jihad, or when it's for a cause, that's the only time Allah allows it. But not to put your life to waste and to just hang yourself like you say you want to do." Jana asked Khalil directly whether he wanted to hurt anybody else.

• 49:26Speaker 00

  "I would not like to hurt somebody else," he replied.

• 49:31Speaker 00

  Towards the end of their conversation, Khalil said that he couldn't stand the thought of being incarcerated.

• 49:39Speaker 00

  If the police tried to take him into custody again, he planned to try and stab them to incite them to kill him in response. But at no time did he discuss planning or intending to carry out a terrorist attack.

• 49:57Speaker 00

  Two days after this conversation, FBI agents arrested Khalil Rayyan at his place of work.

• 50:13Speaker 00

  Case file will be back shortly. Thank you for supporting us by listening to this episode's sponsors.

• 50:21Speaker 00

  This episode is sponsored by Vinted. We all hold on to things we know we're never going to wear again. I've got band t-shirts and hoodies tucked away in my wardrobe that no longer fit, and I know that some of them haven't seen the light of day in a very long time. It's a shame to have perfectly good clothes sitting there when someone else could get plenty of wear out of them, and if you can make a bit of extra money in the process, even better. Thankfully, there's an easy way to pass those clothes on. Vinted is a secondhand marketplace app that makes it easy to sell the clothes you no longer wear, find great deals, and give quality items a second life. All you need to do is add some photos, a description, and a price.

• 51:06Speaker 00

  When something sells, Vinted creates a prepaid shipping label for you, so there's no complicated postage process. Plus, there are no seller fees, so you keep what you earn from every sale. Whether you're clearing out your wardrobe or making room for something new, Vinted makes it easy to turn those unworn clothes into extra cash. And the app is free to download. Give your clothes a second life with Vinted. Download the Vinted app for free to start selling with no seller fees, so you keep everything you earn.

• 51:43Speaker 05

  I'm Jake Stauk, co-founder and CEO of Serval. We built Serval to automate the IT work that slows companies down. Onboarding, password resets, access to applications, my laptop stopped working. While employees wait for help, their real work is put on hold. IT desperately wants to automate this work, and that's why they need Serval. You just tell Serval what you want to automate in plain English, and it's built. No drag-and-drop workflows, no expensive consultants. Employees get unblocked, and IT teams go from drowning in tickets to building what actually matters. With Serval, IT becomes the AI engine powering the entire company. This is a new way to run IT.

• 52:24Speaker 05

  We guarantee you'll automate 50% of all tickets, and we'll prove it to you in a free four-week pilot.

• 52:31Speaker 05

  Go to serval.com/tickets. That's S-E-R-V-A-L dot com slash tickets.

• 52:42Speaker 00

  Thank you for listening to this episode's ads. By supporting our sponsors, you support Casefile to continue to deliver quality content.

• 52:58Speaker 00

  To Khalil's defence attorneys, it appeared as though the FBI had repeatedly tried to manipulate their client towards committing an act of terror. They believed that both female personas the government had used to communicate with Khalil had been part of a “reprehensible drama”. First, they manipulated the young man to fall head over heels in love with Gada, leaving him broken-hearted when she abruptly dumped him. They then introduced him to Jana, who had just lost her fiance, as Khalil had lost his.

• 53:36Speaker 00

  Jana was an attempt to exploit his devastation and loss by pushing him towards terrorism. Instead of just gauging where Khalil stood when it came to such crimes, Jana had actively and repeatedly steered him towards them by promoting jihad. When Khalil expressed suicidal thoughts and revealed a suicide plan, Jana told him the only way suicide was acceptable was in the form of a suicide attack that would also harm others. Near the conclusion of their motion, Khalil’s attorneys wrote: “The government has indiscriminately thrown damaging information about Mr. Rayyan into

• 54:19Speaker 00

  the public record, allowing the media to run wild with the accusations that he is a mentally ill terrorist sympathizer. The truth is that the government has subjected the defendant, a US citizen, to a relentless and cynical emotional manipulation in an attempt to radicalise a lonely young man who was looking for a wife to start a family.”

• 54:45Speaker 00

  A psychologist hired by the Defense found that Rayyan's level of dangerousness was very low. According to an article in The Intercept, the psychologist wrote in his report that Rayyan's comments and behavior with the undercover agent was: "The result of deep longings for female attention in a very shy and awkward young man. His verbalization was the result of an effort to keep the attention with hopes of a future. They were not the result of radicalization or representative of terrorist intentions."

• 55:25Speaker 00

  According to author and journalist Trevor Aronson, who published a book titled "The Terror Factory: Inside the FBI's Manufactured War on Terror", the FBI was using more than 15,000 informants in counterterrorism investigations in early 2016. At that time, many of their investigations focused on alleged Islamic State sympathizers.

• 55:52Speaker 00

  The particular type of surveillance used in Khalil Rayyan's case was known as a "honey pot", an operational practice where a covert agent uses the allure of a romantic or sexual relationship to compromise a target.

• 56:07Speaker 00

  An article in the Detroit Free Press around the time of Khalil's conviction quoted the head of the FBI in Detroit as defending these undercover operations, saying they "only targeted individuals who had already expressed intentions to commit criminal behavior." He described informants as "a legitimate tool in combating terrorism."

• 56:32Speaker 00

  Two other men in Detroit also faced court in early 2016 after being targeted by FBI informants for terror-related activities. But, like Khalil, they were never charged with any offenses relating to terrorism.

• 56:49Speaker 00

  Local Muslim leaders accused the FBI of pursuing young men who were mentally unstable or suffering from emotional problems and goading them into terrorism.

• 57:01Speaker 00

  Other young Muslims in Michigan said that they had been pressured to become informants for the FBI. One young man was interrogated at the airport after returning home from Yemen and said he'd been told that if he became an informant, he would be taken off a no-fly list.

• 57:19Speaker 00

  Another man said he was asked to spy on other Muslims in exchange for a visa allowing him to work in the US.

• 57:29Speaker 00

  In an interview with RT America, author and journalist Trevor Aronson stated:

• 57:36Speaker 00

  “In the vast majority of cases where the FBI uses informants and sting operations and files terrorism-related charges, they’re not finding people who have weapons and bombs and direct connections to terrorist organizations. Instead, more than anything, they’re finding people who are mentally ill. What’s particularly problematic about these cases is they’re not finding the truly dangerous person who would strike tomorrow. Instead, they’re finding someone who is easily manipulated via an informant.”

• 58:13Speaker 00

  There are also arguments that building cases against radicalized individuals via undercover agents isn’t an effective way to prevent terrorism. In many instances, this approach pushes people towards criminal activity instead of away from it.

• 58:31Speaker 00

  In Denmark, a program was introduced that focused on deradicalizing citizens who had chosen to support Islamic State. Creators of the program recognized that young people drawn to YS were typically second-generation immigrants who felt isolated and abandoned by their communities. They designed a collaborative approach between police, Danish intelligence, social services, the healthcare system, and education providers that would see radicalized citizens receive counseling, mentoring, and support as long as they hadn’t committed any crimes.

• 59:10Speaker 00

  Named the Orhus model, it appeared to have some success. While 30 Danish citizens travelled to Syria to join Islamic State in 2013, that number dropped to 1 a year later, and 2 in 2015.

• 59:28Speaker 00

  One young man who took part in the Orhus model spoke with the BBC about his experience. Going by the name of Ahmed, he explained that after he came to police attention for extremist leanings, they approached him at home and took him out for a coffee. They then introduced him to a mentor, another Muslim man who worked with Ahmed for months to deradicalise him and show him he had other options. The programme ultimately worked, with Ahmed telling the BBC: “I’m happy right now, I see my future in Denmark. I couldn’t see that before, because it was all dark.”

• 1:00:12Speaker 00

  Khalil Rayyan spent almost 4 years incarcerated at a federal prison in Indiana.

• 1:00:19Speaker 00

  For the first 6 months, he was held in solitary confinement for his own protection. Prison officials felt that the high-profile nature of Khalil’s case and the allegations of terrorism could lead to other inmates harming Khalil.

• 1:00:35Speaker 00

  In an interview with the Gravel Institute, Khalil stated that his time in solitary confinement permanently altered him. He felt forgotten by his family and hopeless about his future.

• 1:00:49Speaker 00

  “I really do firmly believe that a part of me actually did break when I was in there.”

• 1:00:56Speaker 00

  Eventually Khalil joined the general population. He developed a routine that involved lots of reading, praying, and working in the prison commissary.

• 1:01:08Speaker 00

  Khalil Rayyan was released from custody in June 2020. He returned to his family in Dearborn Heights and also rejoined social media. He soon found a niche on the platform TikTok where he posted videos answering questions about what life was like in prison. Khalil also began a serious relationship with his first real girlfriend, though he struggled with trust issues for a long time. He couldn't shake the fear that his girlfriend might actually be an undercover informant.

• 1:01:43Speaker 00

  Khalil Rayyan has shared his story in a number of interviews. He is adamant that the FBI knew exactly where his life was lacking and how vulnerable he would be to a honeypot approach.

• 1:01:56Speaker 00

  He has also been at pains to make clear how little of a threat he was to the American people, as he never had any plans to launch an attack. Khalil has pointed to the grand jury's dismissal of any terrorism charges against him as proof of this. Quote: "My lawyer, he gave me this quote that a grand jury indicts a ham sandwich, meaning, whatever charges you put on a grand jury, the grand jury is going to indict you on. And for them to return back with no indictment on terrorism really just goes to show that the prosecution didn't have proof beyond reasonable doubt that there was some kind of crime committed there."

• 1:02:41Speaker 00

  In 2024, Khalil spoke with Rolling Stone about issues facing the young Muslim population of Dearborn Heights in the present day. He said that he still lives in fear that he might one day be stopped or raided again by the FBI, adding: "That kind of stuff doesn't go away."

• 1:03:29Speaker 05

  I'm Jake Stauck, co-founder and CEO of Serval. We built Serval to automate the IT work that slows companies down. Onboarding, password resets, access to applications, my laptop stopped working. While employees wait for help, their real work is put on hold. IT desperately wants to automate this work, and that's why they need Serval. You just tell Serval what you want to automate in plain English, and it's built. No drag and drop workflows, no expensive consultants. Employees get unblocked and IT teams go from drowning in tickets to building what actually matters. With Serval, IT becomes the AI engine powering the entire company.

• 1:04:08Speaker 05

  This is a new way to run IT. We guarantee you'll automate 50% of all tickets and we'll prove it to you in a free four-week pilot.

• 1:04:17Speaker 05

  Go to serval.com/tickets. That's S-E-R-V-A-L dot com slash tickets.

• 1:04:25Speaker 06

  500 orders a month was manageable. 5,000 is madness. Embrace intelligent order fulfillment with ShipStation. The only platform combining order management, warehouse workflows, inventory, returns, and analytics in one place. What used to take five separate tools, ShipStation does in one. Automate fulfillment and rate shopping to ship up to 15 times more with up to 90% savings. Go to shipstation.com and use code AUDIO to try ShipStation free for 60 days.