Casefile True Crime - Case 324: Khalil Rayyan

Episode Date: August 9, 2025

*** 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 on...line. 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 HostResearch & writing – Erin MunroCreative direction – Milly RasoProduction & music – Mike MigasAudio editing – Anthony TelferSign up for Casefile Premium:Apple PremiumSpotify PremiumPatreonFor all credits and sources, please visit https://casefilepodcast.com/case-324-khalil-rayyan Hosted on Acast. See acast.com/privacy for more information.

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Starting point is 00:02:29 in December 2015, a 21-year-old man from Michigan admitted something very disturbing to his girlfriend. Khalil Rayan had met 19-year-old Jauna 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. Khalil and Xana would often talk about heavy topics,
Starting point is 00:03:13 including violent crimes committed by the terrorist group, Islamic State. 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.
Starting point is 00:03:41 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. 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.
Starting point is 00:04:14 He had an AK-47 rifle, so he would be capable of shooting many victims. When Xanaar 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. Khalil Ryan was raised in the Detroit suburb of Dearborn Heights, which had a large Arab-American population. Many women in the area wore hijaps, a head covering wrapped over the hair and beneath the chin. Some men wore long, loose-fitting robes known as a thob, and the call to prayer could be heard echoing through parts of the suburb five times a day.
Starting point is 00:05:24 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. He had six younger siblings and step-siblings, but despite growing up in an Arab-American family and neighbourhood, 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. In September 2001, when Khalil was seven years old, the 9-11 attacks changed everything. They were committed by 19 terrorists, all of whom were extremist Muslims affiliated with the jihadist group Al-Qaeda, an armed militant organization dedicated. to establishing fundamentalist Islamic states.
Starting point is 00:06:26 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. Although he lived in a strong Arab-American community, in a broader sense, Khalil felt like an outsider. As he grew older, he became more troubled. At the age of 12, 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.
Starting point is 00:07:08 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. 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 17, he'd started using cannabis. 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.
Starting point is 00:08:04 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 70 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 19, he was often smoking. between 10 and 15 cannabis joints a day.
Starting point is 00:08:50 To make matters worse, Khalil often felt unsafe while working. Detroit could be a dangerous city, and Kalil 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, Kalil would pull up at an address to deliver a Peter, 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. Feeling lonely, angry and powerless, Kalil suffered something of an identity crisis, wondering
Starting point is 00:09:37 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 I.S. had captured the world's attention. Militants from IS had taken over large territories in eastern Syria
Starting point is 00:10:23 where there was an ongoing civil war and northwestern Iraq where local military forces were dwindling. 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. 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. 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 radicalised sympathetic individuals abroad.
Starting point is 00:11:24 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 a Jordanian pilot they had captured, set on fire and burned to death. Others showed men who were suspected by IS of being gay, being thrown off a high-rise building as a form of execution. I.S. 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 Irvay Gordell was kidnapped in Algeria, then held hostage before being beheaded.
Starting point is 00:12:18 This crime was filmed and released online under the title, A Message of Blood for French Government. Khalil Rayan had a Twitter account using the handle at Kalil Ray 21. 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, re-sharing them on his own profile, or reply with a comment. 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.
Starting point is 00:13:15 Kalil sent some photos of beheadings to his brother. He saved one such photo as the screensaver on his smartphone. 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 Tohide, a term referring to the oneness of God.
Starting point is 00:13:56 Neither of Khalil's friends were making the gesture. On Thursday, February 19, 2015, Khalil shared this photograph on his Twitter account. 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. On Monday, October 5, Kalil went to a Dearborn Heights sporting goods store and purchased a 22-cali-cali-Rouber revolver. 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. Question 11E on the form asked,
Starting point is 00:14:47 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 century. As he was driving away from the pizzeria, he noticed two police cars with their lights on signaling him to pull over. Khalil did so at a nearby intersection. 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.
Starting point is 00:15:37 When the officers reached Khalil, they noticed a strong smell of cannabis and asked Kalil 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. Another pointed to some prayer beads Khalil had hanging from his rearview mirror
Starting point is 00:16:07 and said they'd stopped him for obstruction of vision. K-9 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. Michigan was an open carry state, meaning residents were permitted to carry firearms provided they were displayed openly.
Starting point is 00:16:46 To conceal carry, you needed a special license. Khalil did not have this license, and, hiding a gun under his driver's seat, counted as concealment. Khalil waved 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. Khalil Ryan spent the night in jail and was released on Bond the following morning. Khalil was charged with carrying a concealed weapon and a legal possession of a controlled substance one month later.
Starting point is 00:17:39 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. 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. He captioned the photo, Sarwat hunting.
Starting point is 00:18:29 Sarwat 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. About one week after Ryan posted this photo, he received a direct message on Twitter from a 23-year-old woman called Garda. She'd noticed his account and was reaching out. Garda told Khalil she was of Pakistani descent and lived in Cleveland, Ohio. 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.
Starting point is 00:19:18 Kalil thought she was beautiful. The pair exchanged phone numbers and soon they were texting each other daily. 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. Khalil told Garda 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 in games,
Starting point is 00:19:59 Although he was yet to meet Garda 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. Don't cry, my love, please, Garda replied. It's tears of joy, Khalil reassured her. I never felt this way before. The love-struck young couple discussed what their wedding would be like and how many children they would have. Eager to progress to the next stage of their relationship, Khalil said he didn't
Starting point is 00:20:44 want them to sneak around behind their family's backs. Instead, their parents should meet one another. He spoke about it with his father, who said he was happy to go to Ohio with Khalil to meet Garda and plan their wedding. Kalil went back to Garda to share the news, but wasn't met with the joy he expected. Instead, Garda said she was having second thoughts about everything and wasn't sure it was a good idea. She then stopped responding to Kalil altogether, He was heartbroken and distraught. Their relationship had ended as quickly as it began. Khalil wondered if he'd been too clingy or rushed the situation.
Starting point is 00:21:37 Whatever had gone wrong, he believed that must have been his fault. Case file will be back shortly. Thank you for supporting us by listening to this episode's sponsors. Say hello savings and goodbye worries with Freedom Mobile. Get 60 gigs to use in Canada, the US, and Mexico for just $39 bucks a month. Plus get a one-time use of five gigs of roam beyond data. Conditions apply, details at freedommobile.ca. What matters most to you?
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Starting point is 00:23:32 By supporting our sponsors, you support Case File to continue to deliver quality content. A couple of weeks after Garda disappeared, Khalil received a direct message. from another young woman on Twitter. Her name was Jana bride, 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.
Starting point is 00:24:10 Jana told Khalil that she felt an overwhelming urge to talk to him, and she believed God had connected them. 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 Amad who had died during an airstrike in Syria. Two of Jana's cousins had also been killed by anti-IS forces. Now she was living at home with her parents whom she felt were destroying her life. Zana was suicidal and needed somebody to talk to.
Starting point is 00:24:53 Over the course of mid to late December 2015, Khalil and Jana began communicating daily. Kalil 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. 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.
Starting point is 00:25:28 Jana was a staunch supporter of the group as she blamed their enemies for the deaths of her fiancé 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-E. He'd chosen it as a target because lots of people went there, and he knew the parishioners would be unarmed. Khalil told Xana he would show no mercy, even killing women and children. Honestly, I regret not doing it.
Starting point is 00:26:06 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. 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. Jhanna understood where Khalil was coming from.
Starting point is 00:26:44 She told him, Jihad is my dream. She was suicidal, but only had interest in dying if she could martyr herself for God and as revenge for the deaths of Syrians and Iraqis following international invasions. The following month, Khalil told Xana 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. He claimed that sometimes Satan spoke to him at night,
Starting point is 00:27:21 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 high. hospital. Kalil said he wanted to commit a, quote, martyrdom operation at the hospital, killing the officer in the process. Kalil also said he was now carrying a large knife or sword in his car in case he ever got into a fight. He told Xana that his father knew about Kalil's
Starting point is 00:28:05 support of IS and that he'd told his father that he wanted to make jihad. Kalil's father did not support this and had warned his son to be careful about what he said and posted online. On Thursday, February 4, 2016, Khalil received a text message from Xana 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,
Starting point is 00:28:52 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. 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.
Starting point is 00:29:23 His mother and younger sister were escorted from the premises while his younger brother was handcuffed. Khalil Ryan was taken to the FBI headquarters and placed in an interrogation room. An agent informed him that he was under arrest for position. of a firearm by an unlawful user of a controlled substance. Khalil already knew he had state charges pending for these offenses and wasn't aware they'd been upgraded to a federal level. He requested a lawyer several times, but the FBI agent
Starting point is 00:29:59 told him he had some questions to ask first. What is your involvement with Islamic State, the agent asked. At that point, Khalil realized he was under-immonished. He was under-immsman. investigation for terrorism. He responded by asking what he was being charged with. 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 a Jhana, implying that she was being questioned simultaneously in the room next door.
Starting point is 00:30:38 The agent knew about things the two had. disgust, like Khalil's plan to commit a mass shooting at a church and his desire to behead people. At that point, Khalil began to worry about Xana. If the FBI had evidence against them, he wanted to take the rap so she could go free. Despite the agent's questions, no additional charges were laid against Khalil, nor was he charged with anything relating to terrorism. But this time, he wasn't being released on bond. He was to be held in federal custody until his case was resolved. Almost two weeks later, on Tuesday, February 16,
Starting point is 00:31:26 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. As Khalil sat in court, his attorney went through his charge sheet. After reading it, she turned to Kalil and told him that the woman he knew was his girlfriend, Jeanne Bride, didn't exist at all.
Starting point is 00:32:08 It turned out that the FBI had been monitoring Khalil Ryan 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. The FBI began investigating Khalil via a number of methods, including monitoring, of his social media accounts and surveillance. A few months after they first began surveilling Khalil, the FBI became aware that he'd bought a firearm.
Starting point is 00:32:50 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 Garda. Garda initiated a whirlwind romance with Khalil via Twitter,
Starting point is 00:33:29 and he had believed that they were engaged to be married. But then Garda abruptly entered the relationship, leaving Khalil, feeling broken. A few days after Khalil last heard from Garda, either the same agent or another one reached out to Khalil again with a brand-new persona. Unlike Garda, 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.
Starting point is 00:34:08 to the topics of G-yard, martyrdom, and IS. 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. 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.
Starting point is 00:34:50 It was a large building with the capacity to fit 6,000 people. 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 Xana how he carried a sword in his car, and added, I would gladly behead people if I needed to. 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. In the days following Khalil Ryan's second arrest,
Starting point is 00:35:39 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. The FBI's criminal complaint against Khalil was also shared online. 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 Rayan
Starting point is 00:36:25 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. Kalil 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. However, the grand jury did not indict Khalil on any terrorism charges. On Tuesday, September 13, 2016, Khalil faced court.
Starting point is 00:37:21 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 state charges relating to the same offences, and the evidence against him was clear. 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.
Starting point is 00:37:58 Sentencing guidelines for these. 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 Kalil had shared with the genre. The judge also cited the photo Kalil 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.
Starting point is 00:38:42 He sentenced Khalil Ryan to five years in federal prison. Although the shocking headlines about Khalil's planned terrorist attacks had scared some members of the public, there were others who harboured 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. What hadn't been included in the FBI's criminal complaint against Khalil Rayan 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 Jhanna, with nothing at all provided from before December 23, 2015, well-in to the pair's
Starting point is 00:39:40 relationship. The government claimed these emissions were due to a printing error, but Khalil's defense team suspected otherwise. They filed a motion for discovery to gain access to the FBI's full key. case against Khalil. 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 Xana that were available still provided greater clarity as to what had actually
Starting point is 00:40:14 taken place. From the start, Janna 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 Zana and asked her to marry him. Lonely and depressed, Khalil had never had a romantic relationship before and saw marriage
Starting point is 00:41:02 as a way to be happy. He tried to dissuade Jana from harming herself for 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? 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.
Starting point is 00:41:39 I want to start a family. 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.
Starting point is 00:42:06 In subsequent conversations, Jana spoke of wanting to martyr herself for Allah or God, stating, I want to die for the sake of Allah. Her motivation for doing so was vengeance for, quote, 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, Xana responded. But Khalil didn't pick up on these threads, instead trying to convince Jhanna that marriage and building a future was the best path forward.
Starting point is 00:42:49 During one conversation, Xana 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. 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.
Starting point is 00:43:19 At one point, he grew so tired of Xana'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. This time, when Xana began fixating on Islamic State and Jihad again,
Starting point is 00:43:55 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, quote, turning her on. So, he decided to go along with it to impress Jana and maintain her interest. Whenever he turned to other topics, Zana became distant and started to pull away. Desperate to keep her attention,
Starting point is 00:44:25 Khalil started making up stories, claiming he'd been accused of murder and had spent three months in prison before being let go. 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 Zana would be interested in.
Starting point is 00:44:50 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 Peter, sometimes at gunpoint, he felt he needed to be armed for protection. 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.
Starting point is 00:45:36 Khalil had also told Zana he'd bought a mask to wear during the church attack, but no such mask was recovered during searches by the FBI. 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. The situation between Ryan and Ajana reached a boiling point in early February 2016. Ryan 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.
Starting point is 00:46:29 There were also photos of him posing with guns at the firing range. He worried these might lead to further charges. During a phone conversation on Tuesday, February 2, Rayan 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 seemed to be under surveillance. There were always cop cars near his workplace or dark vehicles
Starting point is 00:47:18 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. 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. Zana pushed back against Rayan'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.
Starting point is 00:48:05 Zana asked Khalil directly whether he wanted to hurt anybody else. I would not like to hurt somebody else, he replied. Towards the end of their conversation, Khalil said that he couldn't stand the thought of being incarcerated. 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. Two days after this conversation, FBI agents arrested Khalil Ryan at his place of work. Case file will be back shortly. Thank you for supporting us by listening to
Starting point is 00:49:05 this episode's sponsors. Say hello savings and goodbye worries with Freedom Mobile. Get 60 gigs to use in Canada, the U.S., and Mexico for just $39 a month. Plus get a one-time use of five gigs of roam beyond data. Conditions apply, details at freedommobile.ca. Searchlight Pictures presents The Roses, only in theaters, August 29. From the director of Meet the Parents and the writer of Poor Things comes The Roses, Starring Academy Award winner Olivia Coleman, Academy Award nominee Benedict Cumberbatch, Andy Samburg, Kate McKinnon, and Alison Janney,
Starting point is 00:49:42 a hilarious new comedy filled with drama, excitement, and a little bit of hatred, proving that marriage isn't always a bed of roses. See The Roses only in theaters August 29. Thank you for listening to this episode's ads. By supporting our sponsors, you support Case File to continue to deliver quality. content. To Khalil's defense 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, quote, reprehensible drama. First, they manipulated the young men.
Starting point is 00:50:35 to fall head over heels in love with Garda, leaving him broken-hearted when she abruptly dumped him. They then introduced him to Jana, who had just lost her fiancé, as Khalil had lost his. 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, Jhanna had actively and repeatedly steered him towards them by promoting jihad.
Starting point is 00:51:09 When Khalil expressed suicidal thoughts and revealed a suicide plan, Jhanna 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. Ryan into 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. A psychologist hired by the
Starting point is 00:52:01 defense found that Ryan's level of dangerousness was very low. According to an article in The Intercept, the psychologist wrote in his report that Ryan'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. 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
Starting point is 00:53:00 investigations focused on alleged Islamic State sympathizers. The particular type of surveillance used in Khalil Ryan's case was known as a honeypot, an operational practice where a covert agent uses the allure of a romantic or sexual relationship to compromise a target. 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 behaviour.
Starting point is 00:53:39 He described informants as a legitimate tool in combating terrorism. 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 offences relating to. terrorism. Local Muslim leaders accused the FBI of pursuing young men who were mentally unstable or suffering from emotional problems and goading them into terrorism. 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,
Starting point is 00:54:29 he would be taken off a no-fly list. Another man said he was asked to spy on other Muslims in exchange for a visa, allowing him to work in the US. In an interview with RT America, author and journalist Trevor Aronson stated, 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.
Starting point is 00:55:11 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. There are also arguments that building cases 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. In Denmark, a program was introduced that focused on deradicalizing citizens who were 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
Starting point is 00:56:03 by their communities. They designed a collaborative approach between police, Danish intelligence, social services, the healthcare system and education providers that would see radicalised citizens receive counselling, mentoring and support as long as they hadn't committed any crimes. Named the Orhus model, it appeared to have some success. While 30 Danish citizens traveled to Syria to join Islamic State in 2013, that number dropped to one a year later and two in 2015. 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
Starting point is 00:56:53 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 de-radicalize him and show him he had other options. The program 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. Khalil Ryan spent almost four years incarcerated at a federal prison in Indiana. For the first six 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
Starting point is 00:57:44 terrorism could lead to other inmates harming Khalil. In an interview with the grassroots, Institute, Khalil stated that his time in solitary confinement permanently altered him. He felt forgotten by his family and hopeless about his future. Quote, I really do firmly believe that a part of me actually did break when I was in there. Eventually, Khalil joined the general population. He developed a routine that involved lots of reading, praying and working in the prison commissary.
Starting point is 00:58:22 Khalil Ryan 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. Khalil Rayan has shared his story in a number of interviews.
Starting point is 00:59:01 He is adamant that the FBI knew exactly where his life was lacking and how vulnerable he would be to a Honeypot approach. 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's going to indict you on.
Starting point is 00:59:41 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. 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. Fifty years ago, on the first night in July, 1975, Julian Garcia-Salé vanished. Nine days shy of her 20th birthday,
Starting point is 01:00:42 the Californian teenager who'd been living with her sister in Melbourne was just gone. She wasn't a kid that took off. If she was going someplace she let you know. And I thought, well, she's got to come back. I never dreamed what parent dreams of anything like this. On the evening Julie disappeared, three men shared pizza and beer with her in her inner city apartment. And for the past five decades,
Starting point is 01:01:11 there've been the only persons of interest in the case. I just can't remember the details at all. Right. You know, it was all happy friendly. There was no, you know. We went over there for a drink and that was it. She went away and we got tired of waiting and left. In the days after Julie went missing,
Starting point is 01:01:27 police failed to canvass her neighbours about what they saw that night she disappeared. But Case File presents, has spoken to witnesses who say a young woman was dragged into a car that night from a phone box that was apparently Julie's last known location. Yet, at the time, these witnesses weren't interviewed by police. Three men, they came, they grabbed her. grabbed her and put her into the car and she lost a shoe.
Starting point is 01:01:57 Was it Julie they witnessed being thrown into the car that night? And what happened once the car sped off down the street? They have fully fingerprinted the flat. The chemist took samples of what appeared to be blood from the kitchen, from a tea towel located on Julie's bed, from the bathroom, from a stairwell, and a telephone booth opposite the plat. Julie's mother flew to Australia a couple of times after her 19-year-old daughter disappeared on the first night in July, 1975, imploring police to keep investigating.
Starting point is 01:02:30 I want the police never to close the case. Never. I don't want this case to be closed in the dead file. No charges have ever been laid in this case. In case file presents, Julie's gone, we asked, Is it too late for justice? What happened to Julianne Garsie Salain? And I asked him, what did you do? Please tell me what you did with my daughter. And that's when he took his finger and he went across his neck
Starting point is 01:03:07 like you would cut into somebody's throat. Case File Presents Julie's Gone will be available on July 31st, wherever you get your podcasts. Say hello savings and goodbye worries with Freedom Mobile. Get 60 gigs to use in Canada, the U.S., and Mexico for just $39 a month. Plus get a one-time use of five gigs of Rome Beyond data. Conditions apply, details at freedommobile.ca.
Starting point is 01:03:41 The twisted tale of Amanda Knox is an eight-episode Hulu original limited series that blends gripping pacing with emotional complexity, offering a dramatized look as it revisits the wrongful conviction of Amanda Knox for the tragic murder of Meredith Kircher and the relentless media storm that followed. The twisted tale of Amanda Knox start streaming August 20th only on Disney Plus.

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