But some of the people who grew up with Crimo — a burly, tattooed aspiring YouTube rapper whose music is laced with violent imagery — said they saw troubling warning signs. “There were a lot of red flags with him,” a former Highland Park High School classmate told The Daily Beast. “I told my teacher I didn’t want to sit next to him. It really scared me.” Hours after Highland Park, a town once best known as the setting for Ferris Bueller’s Day Off and Sixteen Candles, became the site of America’s latest mass shooting, a community struggled to process why it was targeted. And why the son of a prominent local businessman running for mayor had descended into a twisted online world obsessed with mass murder, memes and mayhem—and whether he could have been stopped before it was too late. By all accounts, Crimo was not a well-adjusted teenager suddenly thrown off course in recent weeks. On Tuesday, police revealed an incident in September 2019 in which Crimo allegedly threatened to “kill everyone” in that family while collecting 16 knives, a dagger and a sword. He had also attempted suicide that April, police said. Neither incident led to an arrest, which may have made it easier for him to legally purchase the guns police say he used to kill innocent people. A review of Crimo’s social media posts, online speech and music videos shows someone clearly obsessed with violent imagery, mass shootings and high-profile killers. But conversations with people who know him suggested that, even if his behavior was sometimes disturbing, it was difficult to disentangle his more mundane teenage habits, such as his love of hip-hop, from the possibility of evil. “He would always show violent things to everyone,” the same former classmate added, noting that she had a class with Crimo and that he often played. “Violent music videos and lyrics. He would try to promote his rap to everyone.” Authorities have yet to provide a clear picture of any motive behind the fatal shooting. However, they said Crimo spent weeks planning the horrific attack which was launched from a rooftop, where he opened fire on random parade goers waiting for floats and bands he picked up below. Chief Deputy Christopher Covelli, a spokesman for the Lake County Sheriff’s Office, said Tuesday that Crimo wore women’s clothing during the attack “to hide his facial tattoos and his identity and to assist him during the escape with… other people who escaped the chaos. “ He then quickly blended into the chaotic crowd before eventually running to his mother’s house and borrowing her car, police said, noting that he legally took the gun recovered from the rooftop Crimo allegedly used as a sniper’s nest. Crimo has been charged with seven counts of first-degree murder, Lake County State’s Attorney Eric Rinehart said Tuesday, noting that he expects more charges to come. He faces a bond hearing Wednesday morning. On Tuesday, what appeared to be his mother’s home in Highland Park stood out in a manicured neighborhood: the grass and plants were overgrown, and the glass in the front door nearly fell off its pane when it opened. Denise Pesina sat in the driveway in a small white car while talking on the phone with the engine running. She cordially declined to answer questions, referring The Daily Beast to her attorney. No one answered the door at the home of Robert Crimo Jr., the suspected shooter’s father, where the 21-year-old lived in the apartment at the back of the property. It was unclear if and when the parents stopped living together. A car with decals is parked outside the home where Robert Crimo III lives in the Highwood suburb of Chicago, Illinois on July 5, 2022.

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While none of Crimo’s parents responded to requests for comment, their attorney told The Daily Beast they were in “absolute shock” about the allegations against their son. Attorney Steven Greenberg, who previously represented R. Kelly, said the couple “doesn’t know what happened” during the parade — and what could have prompted Krimo to engage in such a horrific plot. “No one believes that a tragedy of this magnitude would happen to their family. When they first heard about the shooting, they had no idea Bobby could be involved.” Greenberg said Crimmo’s parents knew he had legally obtained several firearms in Illinois, but stressed his clients never thought something like Monday’s tragedy could happen. He suggested they cling to the hope that the cops somehow got it wrong — that “it turns out not to be what it seems” because no parent “wants to wake up knowing that their child, who they love and have raised, can spend the rest of their life in prison”. Authorities arrested Crimo after a seven-hour manhunt when a North Chicago police officer spotted the car he was believed to be driving. The 21-year-old fled, but was arrested after a short foot chase in Lake Forest. Inside the car, police said they found a second legally purchased rifle. The fact that Crimo’s parents weren’t exactly nobody made the shooting even more unsettling for some of his former classmates. “His dad ran a popular deli in the area and even ran for mayor in 2019,” Mark Heymann, who was a year older than Crimo at school but said he had known the family for years, told the Daily Beast. Crimo Jr., who lost the race by a two-to-one margin to the incumbent, ran on the slogan “A Person for the People.” A Facebook profile that has since been removed suggests that Crimo’s mother was involved in the world of alternative medicine. Jeremy Cahnmann, who ran an after-school program at Lincoln Elementary School, told Fox News that Crimo’s parents were always the last to pick him and his younger brother up after school. He said Crimo was just nine or 10 years old when he enrolled in the school’s Nerf football program. “I remember the parents more than him, because they were kind of a problem,” Cahnmann said. “The kid was very quiet, very soft-spoken, never caused any trouble.” Several former classmates pointed out to The Daily Beast that Crimo was “quiet”—a “loner” who never really hung out with a group. Heymann, who participated in scouts with Crimo in elementary school, said that “something [was] away, something was wrong with him’ and said he didn’t know ‘if he had any friends’. Another person who was in scouts with Crimo said she lost touch with him after high school but remembered him as a quiet, soft-spoken kid at the skate-park. “He was definitely judged a little bit for his goth image,” the former acquaintance told The Daily Beast. “In Highland Park, it’s not the most distinctive thing.” But the same former classmate said Crimo’s father’s deli, Bob’s Pantry, was a popular place in Highland Park and that he often saw Crimo behind the counter, lending a hand in the family business. In that sense, he seemed like a normal kid to them. “He was never a troublemaker” in high school, the former classmate said, unlike other interviewees. Ethan Absler, another student who was a year ahead of Crimo in high school, insisted the suspect had “behavioral red flags.” In particular, Absler said, he was very challenging in class, constantly promoted his music and was “the type of student where the teachers realized they should discipline him in a different way or be more realistic about his behavior.” But the former classmate still felt there was “nothing to show he was capable of anything” like Monday’s shooting. From Absler’s perspective, Crimo “led, like, a secret double life that we didn’t know about.”

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In high school, Heymann added, Crimo began uploading rap songs to YouTube and went by the name Awake the Rapper on social media. Online, he posted several violent music videos, including a crude animation depicting a gunman being killed by police. In another, Crimo is inside an empty classroom, dressed in uniform and draped with an American flag. NBC News reported that Crimo had his own Discord channel that was deactivated after the shooting — and that he frequented a message board dedicated to death, where he posted a video of a beheading. Crimo’s posts also showed him wearing a Trump flag as a cape. Another photo of Crimo showed him at a Trump rally, dressed as Waldo. But he also liked a video of President Biden on Twitter, and no clear picture of political extremism emerged in the hours after the attack. Two of Crimo’s online friends who also produce music told Rolling Stone that while he struggled with mental health issues and didn’t have many friends in real life, they missed key warning signs. “I knew there was something in his head that was messing with him,” said Nodfather, an indie producer who has been friends with Crimo for years after meeting him on Discord. “In all honesty, a lot of it was him isolating himself.” The former high school classmate who remembered Crimo showing violent content to his classmates noted that he once got in trouble for posting stickers promoting his music on school property. While the classmate mostly forgot about Crimo in the years that followed, she said she wondered if he was the parade shooter when she heard a younger white suspect was on the loose. “This is really weird, but I was saying to somebody, ‘That must be somebody from Highland Park that I know,’ and one of the first things I thought…