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A Deadly Scheme Has an Unexpected Twist

August 09, 2025 / 56:13

This episode covers the case of Khalil Ryan, who in December 2015, confessed to his girlfriend Jeanna Bride about a plan to shoot up a church in Detroit. The discussion includes Khalil's background, his struggles with identity, mental health issues, and his online interactions with Jeanna, who was later revealed to be an FBI informant.

Khalil, a 21-year-old from Michigan, was raised in a strict Muslim family and faced bullying and isolation after the 9/11 attacks. His mental health deteriorated, leading him to use drugs and seek belonging online. He became involved with Islamic State propaganda, which escalated his troubling thoughts.

After a brief romantic relationship with another woman named Garter, Khalil connected with Jeanna, who shared similar feelings of loss and depression. Their conversations quickly turned dark, with Khalil expressing violent fantasies and plans for a mass shooting, which Jeanna encouraged.

In February 2016, the FBI arrested Khalil at his workplace, revealing that Jeanna was an undercover agent. He faced charges related to firearms but was not indicted for terrorism. Khalil's case raises questions about the FBI's tactics in targeting vulnerable individuals.

The episode concludes with Khalil's release from prison in 2020 and his reflections on the impact of his experiences, including his ongoing fears of surveillance.

TLDR

Khalil Ryan's confession of a mass shooting plan leads to FBI arrest, revealing manipulation by an undercover agent posing as his girlfriend.

Episode

56:13
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[Music] Our episodes deal with serious and often distressing incidents. If you feel at
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any time you need support, please contact your local crisis center. For suggested phone numbers for confidential
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support, and for a more detailed list of content warnings, please see the show notes for this episode on your app or on
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our website. This episode was originally released on Case Files Patreon, Apple Premium, and Spotify Premium feeds as an
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early bonus for our paid subscribers. To receive these episodes early and adfree,
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you can support Case File on your preferred platform. [Music] One day in December 2015, a 21-year-old
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man from Michigan admitted something very disturbing to his girlfriend. Khalil Ryan had met 19-year-old Jeanna
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Bride just a couple of months earlier via the social media platform Twitter. The two had bonded over shared interests
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and commonalities. Both were from strict Muslim families and lived in the city of
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Detroit. As they were unable to date openly the way other young people in the United
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States typically would, their relationship had moved quickly and they were already discussing marriage as a
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way to be together. Khalil and Janna would often talk about heavy topics including violent crimes
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committed by the terrorist group Islamic State. During one such conversation in December
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2015, Khalil made an alarming confession. He told Janna, quote, "I tried to shoot up a church one day. I
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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
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out. I bought a bunch of bullets. I practiced a lot with it. I practiced reloading and unloading.
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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
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to wear. Khalil said he'd decided to attack a church because it was an easy target.
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Lots of people would be in attendance and would be unarmed. Plus, it would make the news, he added.
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He had an AK-47 rifle, so he would be capable of shooting many victims. When Jeana asked Khil if he would have
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shot women and children at the church as well as men, he responded, "I would have killed every last one of
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them. I would have shown no mercy. [Music] [Music] Khalil Ryan was raised in the Detroit
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suburb of Dearborn Heights, which had a large ArabAmerican population. Many women in the area wore hijabs, a
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head covering wrapped over the hair and beneath the chin. Some men wore long loose- fitting robes
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known as a th and the call to prayer could be heard echoing through parts of the suburb five times a day.
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Khalil was the son of Palestinian immigrants though his parents split up when he was three. He was then primarily
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raised by his father's family and he received plenty of love and care while at home.
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He had six younger siblings and step siblings. But despite growing up in an Arab-American family and neighborhood,
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Khalil felt torn between two worlds. He also wanted to be an ordinary American kid, so he sometimes went by
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the nicknames K or Ray to sound less foreign. In September 2001, when Khalil was 7
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years old, the 9/11 attacks changed everything. They were committed by 19 terrorists,
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all of whom were extremist Muslims affiliated with the jihadist group al-Qaeda, an armed militant organization
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dedicated to establishing fundamentalist Islamic states. Suddenly, some people in Khalil's
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community began looking at him differently. He was bullied at school for his heritage and began lying about his
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background, telling people he was Hispanic or Italian. Although he lived in a strong
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ArabAmerican community, in a broader sense, Khalil felt like an outsider. As he grew older, he became more
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troubled. At the age of 12, he had a dream that he took a gun to school and shot his entire
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class. He later told a teacher about the nightmare and he was referred to counseling.
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As a teenager, Khalil developed a reputation for being a class clown at the charter high school he attended,
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where the other students were also of mostly Muslim and Arab descent. But he also became the target of bullies
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and was given suspension on at least three separate occasions after getting into fights.
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While his home life was stable, Khalil struggled with his peers and with depression.
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By the age of 17, he'd started using cannabis. It was after graduating, however, that
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Khil's problems escalated. He briefly attended college, but his poor mental health and drug use led to
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him failing his classes. He decided to essentially drop out and take a break from studying to work
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full-time as a pizza delivery driver. Khalil's father was an engineer with two master's degrees, and he also owned a
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pizzeria. Working for his father at the pizzeria seemed like a good solution. However, without the structure of school
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and the friends he'd previously seen daily, Khalil's depression worsened. His job was isolating, involving long
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hours alone in a car, sometimes up to 70 hours a week. Khalil became even more dependent on
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drugs, often smoking between deliveries to curb his boredom and a low mood. By the age of 19, he was often smoking
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between 10 and 15 cannabis joints a day. To make matters worse, Khalil often felt
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unsafe while working. Detroit could be a dangerous city, and Khil was generally working late at
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night. He had to deliver pizza at sketchy looking apartment buildings or on blocks with no porch lights to aid
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visibility. On more than one occasion, Khalil would pull up at an address to deliver a
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pizza, only to find it was an abandoned house, and there were people waiting there to jump and rob him.
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Sometimes Khil was even robbed at gunpoint. Feeling lonely, angry, and powerless,
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Khil suffered something of an identity crisis, wondering who he was and where he belonged.
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He began spending his free time retreating online to seek out a sense of belonging with other young Muslims his
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age. Then he started seeking out shocking and graphic content as a distraction from
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his own feelings. Seeing real gore and violence just felt like an escalation from watching an
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action movie. It involved the same shock and awe on a heightened level. By this time it was 2014 and the actions
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of the terrorist group Islamic State or IS had captured the world's attention. Militants from IS had taken over large
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territories in eastern Syria where there was an ongoing civil war and northwestern Iraq where local military
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forces were dwindling. is declared itself to be a caliphate, the term for a state under the
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leadership of a religious Muslim considered a successor to the Islamic prophet Muhammad.
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Is adheres to a radical pro-Si Islamist ideology and seeks to establish a global
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caliphate through armed struggle. It was designated as a terrorist organization by the United States
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government in April 2014. As they conquered parts of Syria and Iraq, IS became known for their use of
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social media to disseminate their message. They posted news, photos, and videos on
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Twitter as a way to reach a broader audience beyond their geographical borders and radicalize sympathetic
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individuals abroad. Is also became known for their brutality. Much of the content they shared featured
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shocking acts of violence against those they deemed their enemies. One such video was of a Jordanian pilot
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they had captured being set on fire and burned to death. Others showed men who were suspected by IS of being gay being
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thrown off a high-rise building as a form of execution. is also used public beheadings to
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terrorize and punish and filmed soldiers, journalists, aid workers, and others being killed this way.
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In one incident, a French citizen and mountaineering guide named Erve Gordell was kidnapped in Algeria, then held
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hostage before being beheaded. This crime was filmed and released online under the title a message of
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blood for French government. Khalil Ryan had a Twitter account using the handle at Khalil Ray21.
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In November 2014, he started seeking out is content. He liked propaganda posts about their
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victories, including videos of beheadings and the Jordanian pilot's murder. Sometimes he would retweet posts,
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re-sharing them on his own profile or reply with a comment. In one instance, he asked another
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Twitter user if they had a link to a video showing people being thrown from a tall building.
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When the other users shared it with him, Khil replied, "Thanks. That made my day."
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Khalil sent some photos of beheadings to his brother. He saved one such photo as
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the screen saver on his smartphone. Emboldened by the online world he was falling into, Khalil took a photograph
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of himself and two friends, all dressed in camouflage. Khalil was holding a semi-automatic
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pistol in his right hand. His left hand was pointing skyward, his index finger raised.
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This gesture was a commonly acknowledged sign of support for Islamic State known
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as the tohed, a term referring to the oneness of God. Neither of Khalil's friends were making
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the gesture. On Thursday, February 19, 2015, Khil shared this photograph on his Twitter
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account. Throughout 2015, Khalil continued to immerse himself in is content after
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clocking off from work. Late in the year, he decided to buy a gun. On Monday, October 5, Khalil went to a
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Dearbornne Heights sporting goods store and purchased a 22 caliber revolver. To complete the purchase, he had to fill
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out a form required by the Bureau of Alcohol, Tobacco, and Firearms, commonly known as the ATF.
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Question 11E on the form asked, "Are you an unlawful user of or addicted to marijuana or any depressant, stimulant,
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narcotic drug, or any other controlled substance?" Khalil checked no and signed the form.
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2 days later, Khalil left work and got into his 2001 Buick Sentry. As he was driving away from the
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pizzeria, he noticed two police cars with their lights on, signaling him to pull over.
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Khil did so at a nearby intersection. The officers approached him on foot with their weapons drawn, later saying that
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as they did so, they could see him still seated in his car, bending down and making hurried movements as though
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hiding something. When the officers reached Khalil, they noticed a strong smell of cannabis and
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asked Khalil to exit the vehicle. As Khalil did so, he told the officers that his gun was in the car. The
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officers found it on the floor under the driver's seat. When Khalil asked the officers why they
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had pulled him over in the first place, one told him that he'd been speeding. Another pointed to some prayer beads
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Khil had hanging from his rear view mirror and said they'd stopped him for obstruction of vision.
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K9 units were called in and police also recovered a plastic bag under the dashboard which contained a black vial,
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three sleeping pills, and four baggies of cannabis. In total, the search took about 3 hours.
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Khalil was arrested for possession of cannabis and for carrying a concealed weapon.
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Michigan was an open carry state, meaning residents were permitted to carry firearms provided they were
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displayed openly. To conceal carry, you needed a special license. Khalil did not have this license, and
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hiding a gun under his driver's seat counted as concealment. Khalil waved his Miranda rights and
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provided a full statement to the police, stating, "I tried to hide the gun under
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my seat because I panicked. I think my fidgeting made the police officer nervous because he ordered me out of the
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car." That's when I told him, "Hey man, I got a pistol." Khil Ryan spent the night in jail and
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was released on bond the following morning. Khalil was charged with carrying a concealed weapon and illegal possession
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of a controlled substance. One month later at around the same time on Sunday, November 15, he tried to buy another
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gun. He went to a different sporting goods store and again filled out the ATF form
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the same way, but this time his purchase was blocked due to his pending court case.
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Later that day, Khalil and a friend went to a local firing range. The pair rented an AK-47 and an AR-15
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rifle, both of which are military-style firearms. Background checks were not required for
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this. Khalil took photographs of himself holding the weapons and two weeks later
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he posted one of these pictures on Twitter. He captioned the photo saw hunting. Sawat is an is term for a person who
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opposes their group originally referring to the Sunni tribesmen who fought alongside US-led coalition troops in
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Iraq. [Music] About one week after Ryan posted this photo, he received a direct message on
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Twitter from a 23-year-old woman called Garter. She'd noticed his account and was
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reaching out. Garter told Khalil she was of Pakistani descent and lived in Cleveland, Ohio.
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She shared some photos of herself with Khil. Some were selfies she'd taken in front
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of a mirror. Others were her with her family. Khalil thought she was beautiful. The pair exchanged phone numbers and
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soon they were texting each other daily. Khalil had never had a girlfriend before. Their relationship quickly
00:18:04
escalated from getting to know one another by asking questions about their lives to a serious romance where they
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were discussing marriage. Khalil told Garter that his religious faith forbade him from playing games
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with her. If they were going to be together, it needed to be a commitment. Within a week of meeting, they were
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describing themselves as engaged. Although he was yet to meet Garter in person, her presence in Khalil's life
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had already made an enormous impact. In one message, he told her, "While I was driving, I started to cry
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because of how happy I am to have you." "Don't cry, my love. Please," Garter replied. "It's tears of joy," Khalil
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reassured her. "I never felt this way before. [Music] The love struck young couple discussed
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what their wedding would be like and how many children they would have. Eager to progress to the next stage of
00:19:12
their relationship, Khalil said he didn't want them to sneak around behind their family's backs. Instead, their
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parents should meet one another. He spoke about it with his father who said he was happy to go to Ohio with
00:19:27
Khalil to meet Garter and plan their wedding. Khalil went back to Garter to share the
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news but wasn't met with the joy he expected. Instead, Garter said she was having
00:19:42
second thoughts about everything and wasn't sure it was a good idea. She then stopped responding to Khalil
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altogether. He was heartbroken and distraught. Their relationship had ended as quickly
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as it began. Khalil wondered if he'd been too clingy or rushed to the situation.
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Whatever had gone wrong, he believed it must have been his fault. A couple of weeks after Ga disappeared,
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Khalil received a direct message from another young woman on Twitter. Her name was Jeanna Bride and she was of
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Iraqi descent. At 19, she was a few years younger than Garta and she also lived closer to
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Khalil. Like him, she was a Sunni Muslim residing in Detroit. Janna told Khalil that she felt an
00:20:46
overwhelming urge to talk to him and she believed God had connected them. Janna had suffered a lot recently and
00:20:56
was deeply depressed. Like Khalil, she'd experienced heartbreak. She had been engaged to a young man
00:21:04
named Ahmad who had died during an air strike in Syria. Two of Janna's cousins had also been
00:21:12
killed by anti-IS forces. Now she was living at home with her parents whom she felt were destroying
00:21:20
her life. Janna was suicidal and needed somebody to talk to. Over the course of mid to late December
00:21:30
2015, Khalil and Janna began communicating daily. Khalil developed romantic feelings for
00:21:38
Janna quickly, but she was slower to respond. Janna seemed too absorbed by her own
00:21:45
pain to be interested in dating at all. Nevertheless, the two became close and were soon confiding intimate thoughts
00:21:54
and feelings to one another. They found some common ground in their feelings about Islamic State.
00:22:03
Janna was a staunch supporter of the group as she blamed their enemies for the deaths of her fianceé and cousins.
00:22:12
Khalil began confessing some of his darker thoughts to Janna. He told her about a plan he'd had to
00:22:19
shoot up a church near his home with an AK-47. He'd chosen it as a target because lots
00:22:26
of people went there and he knew the parishioners would be unarmed. Khalil told Janna he would show no
00:22:33
mercy, even killing women and children. Honestly, I regret not doing it. If I can't go do jihad in the Middle East, I
00:22:43
would do my jihad over here. Maybe down the line, I can try again. Jihad is an Arabic word that translates
00:22:53
to struggling. In an Islamic context, it can refer to an individual striving to live a moral
00:23:00
life or to put efforts towards building a good Muslim community. However, in the context of extremist
00:23:08
Islam, it has come to mean an armed struggle against perceived enemies of the religion.
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Janna understood where Khalil was coming from. She told him, "Jihad is my dream.
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She was suicidal, but only had interest in dying if she could martyr herself for
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God and as revenge for the deaths of Syrians and Iraqis following international invasions.
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The following month, Khalil told Janna that hearing about shootings and murder excited him.
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I would gladly behead people if I needed to, he said. It is my dream to behead someone.
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He claimed that sometimes Satan spoke to him at night, telling him to burn people
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alive and cut their tongues. Khalil also wanted to murder one of the police officers who'd arrested him for
00:24:05
concealed carry and possession of a controlled substance a few months earlier. Khalil explained that his trial had been
00:24:13
delayed because the officer in question had suffered a heart attack and was in hospital.
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Khalil said he wanted to commit a quote martyrdom operation at the hospital, killing the officer in the process.
00:24:28
Khalil also said he was now carrying a large knife or sword in his car in case he ever got into a fight.
00:24:36
He told Janna that his father knew about Khalil's support of is and that he'd told his father that he wanted to make
00:24:43
jihad. Khalil's father did not support this and had warned his son to be careful about
00:24:50
what he said and posted online. On Thursday, February 4, 2016, Khil received a text message from Jeanna
00:25:05
early in the morning. She asked whether he was going to work that day. Khil replied that he was then got ready
00:25:14
for his shift. He left home and stopped to get gas before driving to work. Khalil was opening up the pizzeria that
00:25:24
day and as he approached the front door, he suddenly saw a man with an AR- style
00:25:29
rifle aimed at him. He ordered Khil to get on the ground. Soon there was a swarm of other people
00:25:38
surrounding him, all brandishing firearms and wearing bulletproof vests. They were agents for the Federal Bureau
00:25:45
of Investigation or FBI. As they placed Khil under arrest and searched the pizzeria, a simultaneous
00:25:54
raid was taking place at his family home. His mother and younger sister were escorted from the premises while his
00:26:02
younger brother was handcuffed. Khalil Ryan was taken to the FBI headquarters and placed in an
00:26:10
interrogation room. An agent informed him that he was under arrest for possession of a firearm by an unlawful
00:26:17
user of a controlled substance. Khil already knew he had state charges pending for these offenses and wasn't
00:26:26
aware they'd been upgraded to a federal level. He requested a lawyer several times, but
00:26:32
the FBI agent told him he had some questions to ask first. "What is your involvement with Islamic
00:26:39
State?" the agent asked. At that point, Khalil realized he was under investigation for terrorism.
00:26:49
He responded by asking what he was being charged with. The agent repeated that it was just a
00:26:55
gun case, but followed up by asking about posts Khalil had shared on social media and his thoughts about Islamic
00:27:03
State. He then brought up Ajanna, implying that she was being questioned simultaneously
00:27:10
in the room next door. The agent knew about things the two had discussed, like Khil's plan to commit a
00:27:18
mass shooting at a church and his desire to behead people. At that point, Khalil began to worry
00:27:26
about Janna. If the FBI had evidence against them, he wanted to take the rap so she could go
00:27:33
free. Despite the agents questions, no additional charges were laid against Khalil, nor was he charged with anything
00:27:43
relating to terrorism. But this time, he wasn't being released on bond. He was to be held in federal custody
00:27:52
until his case was resolved. Almost 2 weeks later on Tuesday, February 16, Khil was charged in a
00:28:02
two-count indictment. He was being charged with making a false statement to acquire a firearm for lying
00:28:10
on the ATF form when purchasing his handgun by stating he wasn't an unlawful user of a controlled substance.
00:28:18
He was also charged with possession of a firearm by a prohibited person. As Khil sat in court, his attorney went
00:28:28
through his charge sheet. After reading it, she turned to Khil and told him that
00:28:33
the woman he knew was his girlfriend, Jeanna Bride, didn't exist at all. It turned out that the FBI had been
00:28:46
monitoring Khalil Ryan ever since May 2015 after his Twitter account came to their attention.
00:28:55
His comments and posts in favor of IS activities had been flagged and a review found that he'd been liking and
00:29:02
retweeting IS propaganda for over 6 months. The FBI began investigating Khalil via a
00:29:10
number of methods, including monitoring of his social media accounts and surveillance.
00:29:17
A few months after they first began surveilling Khalil, the FBI became aware that he'd bought a firearm.
00:29:25
They arranged for local police to pull Khalil over just 2 days after the purchase under the guise of a routine
00:29:32
traffic stop. It was then that Khalil was first charged with criminal offenses for the
00:29:39
concealed carry of the gun and possession of a controlled substance. The FBI has not released the full facts
00:29:47
of their investigation into Khalil, but it is believed that they first attempted
00:29:52
to approach him undercover about 2 months after his arrest using the online persona of Garter.
00:29:59
Garter initiated a whirlwind romance with Khalil via Twitter and he had believed that they were engaged to be
00:30:07
married. But then Garter abruptly ended the relationship, leaving Khalil feeling
00:30:13
broken. A few days after Khil last heard from Garter, either the same agent or another
00:30:21
one reached out to Khalil again with a brand new persona. Unlike a Gata, Janna Bride's approach
00:30:30
was grounded in a strong focus on Islamic State. The agent operating as Janna gave her a
00:30:37
history steeped in conflicts taking place in the Middle East and repeatedly turned their conversations to the topics
00:30:43
of jihad, martyrdom, and is during conversations throughout December 2015 and January 2016. Khalil made a
00:30:55
number of statements that the FBI took as indications he might be planning a terror attack.
00:31:02
These included claims that he'd previously planned to shoot up a church. Based on information in Khalil's
00:31:10
messages, agents were able to identify a church that fit the description he gave.
00:31:16
It was less than half a mile from the pizzeria where Khalil worked and stretched across two blocks.
00:31:24
It was a large building with a capacity to fit 6,000 people. In late January 2016, Khil also talked
00:31:34
about wanting to go to the hospital where the officer who arrested him was being cared for and murdering him.
00:31:41
The next day, he told Jeanna how he carried a sword in his car and added, "I would gladly behead people if I needed
00:31:50
to." About 2 weeks after this, on Thursday, February 4, FBI agents struck. They arrested Khalil at his workplace
00:32:02
and confronted him with what they knew about his terrorist ambitions. [Music] In the days following Khalil Ryan's
00:32:12
second arrest, articles were published about the incident in local and national newspapers and media outlets. Headlines
00:32:20
announced that a 21-year-old man had been arrested on suspicion of supporting Islamic State and planning to attack a
00:32:28
Detroit church. Khalil was portrayed as a dangerous budding terrorist who had been
00:32:34
successfully stopped before he'd caused harm. The FBI's criminal complaint against
00:32:41
Khalil was also shared online. The affidavit contained this notable quote from FBI special agent Alan
00:32:51
Southard. Since May of 2015, the FBI has been conducting an investigation of Khalil
00:32:58
Abu Ryan regarding increasingly violent threats he has made to others about committing acts of terror and martyrdom,
00:33:07
including brutal acts against police officers, churchgoers, and others on behalf of the foreign terrorist
00:33:14
organization Islamic State of Iraq and Lavant. Khalil was held on bond and had to
00:33:22
undergo a competency exam to prove he was fit to stand trial. A grand jury indicted Khalil on the two gun rellated
00:33:30
felonies the FBI had initially charged him with, making a false statement to acquire a firearm and possession of a
00:33:38
firearm by a prohibited person. However, the grand jury did not indict Khalil on any terrorism charges.
00:33:49
On Tuesday, September 13, 2016, Khalil faced court. On the advice of his attorney, he
00:33:57
pleaded guilty to the two federal firearm charges. He had already pleaded guilty to the state charges relating to
00:34:05
the same offenses, and the evidence against him was clear. Khalil told the court of his deep
00:34:12
remorse for his actions, stating, "I am so ashamed. I have humiliated myself. That conduct is not who I am or what I
00:34:22
believe in. Islamic state has nothing to do with Islam. I have shamed my faith. I
00:34:29
have shamed the Muslim people." Sentencing guidelines for these charges typically called for 10 to 16 months in
00:34:38
prison. The judge spoke for an hour before sentencing Khalil, focusing primarily on Khalil's support for
00:34:46
Islamic State. This is not merely viewing an Islamic State website, the judge stated, while
00:34:54
pointing to the threat Khalil had shared with the Janna. The judge also cited the photo Khalil
00:35:01
had posted of himself to Twitter holding a military-grade rifle and claiming he was saw somewhat hunting.
00:35:08
Although Khalil had expressed remorse for holding these sentiments, the judge said his apology was too little too
00:35:15
late. He sentenced Khil Ryan to 5 years in federal prison. Although the shocking headlines about
00:35:27
Khalil's planned terrorist attacks had scared some members of the public, there were others who harbored concerns about
00:35:34
the case against the young man. Civil rights advocates and Muslim American leaders believed Khalil's case
00:35:42
was emblematic of a larger abuse of power taking place. What hadn't been included in the FBI's
00:35:50
criminal complaint against Khalil Ryan was mitigating evidence that indicated he had never had any intention to commit
00:35:57
a terrorist act at all. In fact, the evidence provided by the government was missing key portions of the
00:36:05
conversations between Khalil and Janna with nothing at all provided from before December 23, 2015, well into the pair's
00:36:14
relationship. The government claimed these emissions were due to a printing error, but Khil's
00:36:21
defense team suspected otherwise. They filed a motion for discovery to gain access to the FBI's full case
00:36:29
against Khil. The government was able to successfully withhold most of its surveillance
00:36:36
evidence by arguing that doing so would protect national security. But a closer look at the conversations
00:36:43
between Khalil and Janna that were available still provided greater clarity as to what had actually taken place.
00:36:52
From the start, Jeanna bride had presented as a deeply depressed suicidal young woman who had suffered immense
00:37:00
loss. While she had repeatedly raised the subject of Islamic State and Jihad, Khalil's responses to her had been more
00:37:09
focused on building a romantic relationship. "I wish I could take you away from this
00:37:15
sadness," he wrote. "I pray a lot for your happiness. Sometimes I think I see you in my dreams."
00:37:24
Over time, he started professing his love to Janna and asked her to marry him. Lonely and depressed, Khalil had never
00:37:33
had a romantic relationship before and saw marriage as a way to be happy. He tried to dissuade Janna from harming
00:37:41
herself or others, telling her, "Just stay positive. Everything will work out." In one conversation, Janna expressed her
00:37:52
deep sadness before asking Khalil, "What do you want from this dunya?" Dunya is an Arabic word referring to the
00:38:02
temporal world. Khalil replied, "Honestly, to get married, I think if I get married, I will be happy. I'm just
00:38:12
lonely sometimes. I want to start a family." "What about the afterlife?" Jeanna asked
00:38:20
before adding, "I want to leave this dunya. I don't want to get married." Khalil encouraged her not to give up,
00:38:29
reassuring her that her life would improve. "Don't you want to have children and
00:38:34
watch them grow up?" he asked. "That's probably the best feeling." In subsequent conversations, Jeanna
00:38:44
spoke of wanting to m herself for Allah or God, stating, "I want to die for the sake of Allah." Her motivation for doing
00:38:54
so was vengeance for quote. Seeing my sisters and brothers and young women die in Syria and Iraq like that.
00:39:04
Khalil replied that she was young and confused and didn't know what she wanted. Jihad is my dream. Jeanna responded.
00:39:15
But Khalil didn't pick up on these threads. instead trying to convince Jeanna that marriage and building a
00:39:22
future was the best path forward. During one conversation, Jeanna appeared to directly ask Khalil about a possible
00:39:31
plan for them to commit jihad together, writing, "So, you don't want to do anything of
00:39:37
what we talked about together?" "No, I can't." Khalil replied, "I want us to be together. I have other plans.
00:39:48
Don't do anything that will hurt yourself or other people. At one point, he grew so tired of
00:39:57
Jeanna's repeated talk about jihad that he stopped talking to her for 3 days. She continued to contact him incessantly
00:40:06
during that time. Perhaps picking up on his distaste for conversations about violence, she no
00:40:14
longer messaged about that, but instead said how much she needed someone to talk
00:40:18
to. Khalil caved and resumed contact. This time, when Jeanna began fixating on Islamic State and Jihad again, Khalil
00:40:30
followed her lead. He would later explain in an interview with progressive advocacy group the
00:40:37
Gravel Institute that he could see those were the things that were quote turning
00:40:42
her on. So he decided to go along with it to impress Jeanna and maintain her interest.
00:40:51
Whenever he turned to other topics, Janna became distant and started to pull away.
00:40:58
And desperate to keep her attention, Khalil started making up stories, claiming he'd been accused of murder and
00:41:05
had spent 3 months in prison before being let go. This had never happened. Khalil said that his claims of wanting
00:41:14
to behead people or commit a massacre at a church were invented as well to make him sound more like the sort of man
00:41:22
Jeanna would be interested in. When the FBI searched Khalil's home and workplace, they found no trace of the
00:41:30
AK-47 he said he'd owned. The truth was that Khalil had never owned an AK-47, nor did he have any bullets.
00:41:41
He had purchased a handgun in October 2015, but this was in response to feeling unsafe at work. After being
00:41:49
robbed multiple times while delivering pizzas, sometimes at gunpoint, he felt he needed to be armed for protection.
00:41:58
The gun he bought could only carry six bullets in its chamber. He'd had it for just 2 days when he was
00:42:05
pulled over, and it was confiscated by the police. Khalil had also told Janna he'd bought a
00:42:13
mask to wear during the church attack, but no such mask was recovered during searches by the FBI.
00:42:21
Khalil's defenders have described his proposed massacre as fantasy to impress a girl.
00:42:29
But prosecutors argued that even if he hadn't made preparations to carry it out, his messages were still an
00:42:36
expression of intent. The situation between Ryan and Ajanna reached a boiling point in early
00:42:44
February 2016. Ryan had grown increasingly depressed while awaiting trial for the gun
00:42:51
charges. He was also anxious because his phone had been searched following his arrest and he knew authorities might
00:42:59
find the Islamic State content he had downloaded and watched. There were also photos of him posing
00:43:06
with guns at the firing range. He worried these might lead to further charges. During a phone conversation on Tuesday,
00:43:15
February 2, Ryan told Janna that he was suicidal and had bought a rope to hang himself.
00:43:23
"I'm tired of this," he said. "We're doing the same thing every day." He told Jeanna of his anxieties that he
00:43:32
might be charged with further offenses. He claimed he'd tried to travel to Syria
00:43:38
a year earlier to join Islamic State, but had been turned away. Lately, he'd noticed that he seemed to
00:43:46
be under surveillance. There were always cop cars near his workplace or dark vehicles following
00:43:53
him. One time, Khalil had actually called the police to report that he'd seen a man in
00:43:59
a vehicle taking photos of him. An officer had attended the scene, spoken to the man in the vehicle, and
00:44:07
then told Khalil that it was fine. The man had just been taking photos of some nearby signs.
00:44:16
Janna pushed back against Ryan's suicidal ideiation, telling him that taking his own life was haram forbidden
00:44:24
by Islamic law. When it's for the sake of Allah, when it's jihad, or when it's for a cause,
00:44:32
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
00:44:40
to do. Janna asked Khalil directly whether he wanted to hurt anybody else. I would not like to hurt somebody else,
00:44:51
he replied. Towards the end of their conversation, Khil said that he couldn't stand the
00:44:58
thought of being incarcerated. If the police tried to take him into custody again, he planned to try and
00:45:06
stab them to incite them to kill him in response. But at no time did he discuss planning
00:45:14
or intending to carry out a terrorist attack. 2 days after this conversation, FBI
00:45:22
agents arrested Khalil Ryan at his place of work. [Music] To Khalil's defense attorneys, it
00:45:35
appeared as though the FBI had repeatedly tried to manipulate their client towards committing an act of
00:45:41
terror. They believed that both female personas the government had used to communicate
00:45:47
with Khalil had been part of a quote reprehensible drama. First, they manipulated the young man to
00:45:56
fall head over heels in love with Garter, leaving him brokenhearted when she abruptly dumped him.
00:46:03
They then introduced him to Janna who had just lost her fianceé as Khalil had lost his.
00:46:11
Janna was an attempt to exploit his devastation and loss by pushing him towards terrorism.
00:46:19
Instead of just gauging where Khalil stood when it came to such crimes, Janna had actively and repeatedly steered him
00:46:27
towards them by promoting jihad. When Khalil expressed suicidal thoughts and revealed a suicide plan, Jeanna told
00:46:36
him the only way suicide was acceptable was in the form of a suicide attack that
00:46:41
would also harm others. Near the conclusion of their motion, Khalil's attorneys wrote,
00:46:50
"The government has indiscriminately thrown damaging information about Mr. Ryan into the public record, allowing
00:46:56
the media to run wild with the accusations that he is a mentally ill terrorist sympathizer.
00:47:03
The truth is that the government has subjected the defendant, a US citizen, to a relentless and cynical emotional
00:47:11
manipulation in an attempt to radicalize a lonely young man who was looking for a
00:47:16
wife to start a family. A psychologist hired by the defense found that Ryan's level of dangerousness
00:47:25
was very low. According to an article in The Intercept, the psychologist wrote in
00:47:31
his report that Ryan's comments and behavior with the undercover agent was the result of deep longings for female
00:47:40
attention in a very shy and awkward young man. His verbalization was the result of an effort to keep the
00:47:48
attention with hopes of a future. They were not the result of radicalization or representative of terrorist intentions.
00:48:00
According to author and journalist Trevor Aronson, who published a book titled The Terror Factory: Inside the
00:48:07
FBI's Manufactured War on Terror, the FBI was using more than 15,000 informants in counterterrorism
00:48:15
investigations in early 2016. At that time, many of their investigations focused on alleged
00:48:23
Islamic State sympathizers. The particular type of surveillance used in Khil Ryan's case was known as a
00:48:32
honeypot, an operational practice where a covert agent uses the allure of a romantic or sexual relationship to
00:48:39
compromise a target. An article in the Detroit Free Press around the time of Khalil's conviction
00:48:47
quoted the head of the FBI in Detroit as defending these undercover operations, saying they only targeted individuals
00:48:54
who had already expressed intentions to commit criminal behavior. He described informants as a legitimate
00:49:02
tool in combating terrorism. Two other men in Detroit also faced court in early 2016 after being targeted
00:49:12
by FBI informants for terror related activities. But like Khalil, they were never charged
00:49:19
with any offenses relating to terrorism. Local Muslim leaders accused the FBI of
00:49:27
pursuing young men who were mentally unstable or suffering from emotional problems and goating them into
00:49:34
terrorism. Other young Muslims in Michigan said that they had been pressured to become
00:49:40
informants for the FBI. One young man was interrogated at the airport after returning home from Yemen
00:49:47
and said he'd been told that if he became an informant, he would be taken off a no-fly list.
00:49:54
Another man said he was asked to spy on other Muslims in exchange for a visa, allowing him to work in the US.
00:50:04
In an interview with RT America, author and journalist Trevor Aronson stated, "In the vast majority of cases where the
00:50:13
FBI uses informants and sting operations and files terrorism related charges, they're not finding people who have
00:50:21
weapons and bombs and direct connections to terrorist organizations. [Music] Instead, more than anything, they're
00:50:29
finding people who are mentally ill. What's particularly problematic about these cases is they're not finding the
00:50:36
truly dangerous person who would strike tomorrow. Instead, they're finding someone who is
00:50:43
easily manipulated via an informant. There are also arguments that building cases against radicalized individuals
00:50:52
via undercover agents isn't an effective way to prevent terrorism. In many instances, this approach pushes
00:51:01
people towards criminal activity instead of away from it. In Denmark, a program was introduced
00:51:08
that focused on dradicalizing citizens who had chosen to support Islamic State. Creators of the program recognized that
00:51:17
young people drawn to YS were typically second generation immigrants who felt isolated and abandoned by their
00:51:24
communities. They designed a collaborative approach between police, Danish intelligence,
00:51:31
social services, the health care system, and education providers that would see radicalized citizens receive counseling,
00:51:39
mentoring, and support as long as they hadn't committed any crimes. Named the Orhus model, it appeared to
00:51:47
have some success. While 30 Danish citizens traveled to Syria to join Islamic State in 2013, that number
00:51:56
dropped to one a year later and two in 2015. One young man who took part in the Orhus
00:52:05
model spoke with the BBC about his experience. Going by the name of Ahmed, he explained
00:52:12
that after he came to police attention for extremist leanings, they approached him at home and took him out for a
00:52:19
coffee. They then introduced him to a mentor, another Muslim man who worked with Ahmed
00:52:25
for months to dradicalize him and show him he had other options. The program ultimately worked with Ahmed
00:52:34
telling the BBC, "I'm happy right now. I see my future in Denmark. I couldn't see
00:52:41
that before because it was all dark. Khalil Ryan spent almost 4 years incarcerated at a federal prison in
00:52:52
Indiana. For the first 6 months, he was held in solitary confinement for his own
00:52:58
protection. Prison officials felt that the high-profile nature of Khalil's case and
00:53:04
the allegations of terrorism could lead to other inmates harming Khalil. In an interview with the Gravel
00:53:12
Institute, Khalil stated that his time in solitary confinement permanently altered him. He felt forgotten by his
00:53:19
family and hopeless about his future. quote, "I really do firmly believe that a part of me actually did break when I
00:53:29
was in there." Eventually, Khalil joined the general population. He developed a routine that
00:53:37
involved lots of reading, praying, and working in the prison commissery. Khalil Ryan was released from custody in
00:53:46
June 2020. He returned to his family in Dearbornne Heights and also rejoined social media.
00:53:54
He soon found a niche on the platform Tik Tok where he posted videos answering questions about what life was like in
00:54:00
prison. Khalil also began a serious relationship with his first real girlfriend. Though
00:54:07
he struggled with trust issues for a long time, he couldn't shake the fear that his girlfriend might actually be an
00:54:15
undercover informant. Khalil Ryan has shared his story in a number of interviews. He is adamant that
00:54:23
the FBI knew exactly where his life was lacking and how vulnerable he would be to a honeypot approach.
00:54:31
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
00:54:37
plans to launch an attack. Khalil has pointed to the grand jury's dismissal of any terrorism charges
00:54:45
against him as proof of this quote. My lawyer, he gave me this quote that a grand jury indictes a ham sandwich.
00:54:55
Meaning, whatever charges you put on a grand jury, the grand jury is going to indict you on.
00:55:01
And for them to return back with no indictment on terrorism really just goes to show that the prosecution didn't have
00:55:09
proof beyond reasonable doubt that there was some kind of crime committed there.
00:55:16
In 2024, Khalil spoke with Rolling Stone about issues facing the young Muslim population of Dearbornne Heights in the
00:55:24
present day. He said that he still lives in fear that he might one day be stopped
00:55:29
or raided again by the FBI, adding, "That kind of stuff doesn't go away. [Music]

Badges

This episode stands out for the following:

  • 85
    Most intense
  • 80
    Most shocking
  • 80
    Biggest twist
  • 75
    Most heartbreaking

Episode Highlights

  • Khalil's Disturbing Confession
    Khalil reveals his plan to attack a church, expressing a desire for mass violence.
    “I would have killed every last one of them. I would have shown no mercy.”
    @ 03m 00s
    August 09, 2025
  • A Heartfelt Connection
    Khalil shares his deep feelings for Garter, expressing joy and vulnerability.
    “While I was driving, I started to cry because of how happy I am to have you.”
    @ 18m 43s
    August 09, 2025
  • Escalating Violence
    Khalil shares his dark thoughts about violence and jihad with Janna, revealing his mindset.
    “I would gladly behead people if I needed to, it is my dream to behead someone.”
    @ 23m 44s
    August 09, 2025
  • Khalil's Arrest and Charges
    Khalil Ryan was arrested on suspicion of supporting Islamic State and planning an attack.
    “A 21-year-old man had been arrested on suspicion of supporting Islamic State.”
    @ 32m 23s
    August 09, 2025
  • Khalil's Remorse in Court
    Khalil expressed deep remorse for his actions, stating he had shamed his faith.
    “I am so ashamed. I have humiliated myself.”
    @ 34m 16s
    August 09, 2025
  • Manipulation by the FBI
    Khalil's defense argued that the FBI manipulated him through emotional tactics.
    “The government has subjected the defendant... to a relentless and cynical emotional manipulation.”
    @ 47m 11s
    August 09, 2025
  • The Orhus Model
    A collaborative approach in Denmark aimed at deradicalizing young citizens involved with Islamic State.
    “While 30 Danish citizens traveled to Syria to join Islamic State in 2013, that number dropped to one a year later.”
    @ 51m 51s
    August 09, 2025
  • Khalil Ryan's Solitary Confinement
    Khalil Ryan shares how his time in solitary confinement changed him forever.
    “I really do firmly believe that a part of me actually did break when I was in there.”
    @ 53m 29s
    August 09, 2025
  • Khalil's Story Post-Prison
    Khalil Ryan discusses his life after prison, including struggles with trust and fear of being targeted again.
    “That kind of stuff doesn't go away.”
    @ 55m 33s
    August 09, 2025

Episode Quotes

  • I would have killed every last one of them. I would have shown no mercy.
    A Deadly Scheme Has an Unexpected Twist
  • I tried to hide the gun under my seat because I panicked.
    A Deadly Scheme Has an Unexpected Twist
  • Jihad is my dream.
    A Deadly Scheme Has an Unexpected Twist
  • I am so ashamed. I have humiliated myself.
    A Deadly Scheme Has an Unexpected Twist
  • Don't do anything that will hurt yourself or other people.
    A Deadly Scheme Has an Unexpected Twist
  • My lawyer, he gave me this quote that a grand jury indicts a ham sandwich.
    A Deadly Scheme Has an Unexpected Twist

Key Moments

  • Khalil's Confession03:00
  • Jihad Aspirations23:24
  • FBI Surveillance29:10
  • Romantic Manipulation45:50
  • Emotional Manipulation47:11
  • Radicalization Challenges50:29
  • Khalil's Release53:46
  • Fear of Repercussions55:27

Words per Minute Over Time

Vibes Breakdown