Robert Bobby Crimo III, Alleged Highland Park Mass Shooter, Left Trail of Red Flags

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When Highland Park Mayor Nancy Rotering on Tuesday revealed that she knew Robert “Bobby” Crimo, the 21-year-old accused of indiscriminately raining gunfire on a peaceful July 4 parade in an attack that killed seven and injured dozens more, she expressed shock that a “little boy” from the cub scouts would somehow become a mass killer.

But some of the people who grew up with Crimo—a lanky aspiring YouTube rapper festooned with tattoos, his music riddled with violent imagery—said they saw disturbing warning signs.

“There were lots of red flags with him,” one former Highland Park High School classmate told The Daily Beast. “I told my teacher I didn’t want to sit next to him. He really scared me.”

Hours after Highland Park, a town once best known as the backdrop to Ferris Bueller’s Day Off and Sixteen Candles, became the latest site of mass slaughter by gunfire in America, a community was struggling to process why it became a target. And why the son of a prominent local businessman who ran for mayor had descended into a twisted online world obsessed with mass murder, memes, and mayhem—and whether he might have been stopped before it was too late.

By all accounts, Crimo was not a well-adjusted teen who suddenly veered wildly off course in recent weeks. On Tuesday, police revealed a September 2019 incident in which Crimo allegedly threatened to “kill everyone” in his family while hoarding 16 knives, a dagger, and a sword. He had also attempted to die by suicide that same April, police said.

Neither incident resulted in an arrest, which may have made it easier for him to legally purchase the guns cops say he used to kill innocent people.

A review of Crimo’s social media posts, online discourse, and music videos point to someone plainly obsessed with violent imagery, mass shootings, and high-profile murderers. But conversations with people who know him suggested that even if his behavior was sometimes disturbing, it was difficult to unpack his more banal adolescent habits, like his love of hip hop, from the potential for evil.

“He would always be showing violent things to everyone,” the same former classmate added, noting that she had a class with Crimo and that he frequently acted out. “Violent music videos and lyrics. He would try to promote his rapping to everyone.”

Authorities have yet to paint a clear picture of any motive behind the deadly shooting. But they said Crimo spent weeks planning the horrific attack launched from a rooftop, where he opened fire at random parade attendees awaiting floats and marching bands below.

Deputy Chief Christopher Covelli, a spokesman for the Lake County Sheriff’s Office, said Tuesday that Crimo wore women’s clothing during the attack “to conceal his facial tattoos and his identity, and help him during the escape with… other people who were fleeing the chaos.”

Afterwards, he quickly blended into the chaotic crowd before eventually running to his mother’s house and borrowing her car, police said, noting that he legally obtained the gun they 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 Attorney Eric Rinehart said on Tuesday, noting that he anticipated more charges would be forthcoming. He faces a bond hearing Wednesday morning.

On Tuesday, what appeared to be his mother’s home in Highland Park stood out in a well-kept neighborhood: the grass and plants were overgrown, and the glass on the front door almost fell out its pane when opened.

Denise Pesina sat in the driveway in a small white car while speaking 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 father of the suspected shooter, 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 of the house where Robert Crimo III, lives in the Chicago suburb of Highwood, Illinois, on July 5, 2022.

Photo by MAX HERMAN/AFP via Getty Images

While neither of Crimo’s parents responded to requests for comment, their lawyer told The Daily Beast they were in “absolute shock” over the allegations against their son.

Attorney Steven Greenberg, who previously represented R. Kelly, said that the couple “don’t know what happened” during the parade—and what could have prompted Crimo to be involved in such a grisly plot.

“Nobody thinks a tragedy of this magnitude would happen to their family. When they first heard about the shooting, they had no idea that Bobby could be involved.”

Greenberg indicated that Crimo’s parents were aware that he had legally obtained several firearms in Illinois, but stressed that his clients never thought anything like Monday’s tragedy could happen. He suggested they were clinging to the hope that cops somehow got it wrong—that “it turns out that it’s not what it seems” because no parent “wants to wake up knowing their child, who they love and they have nurtured, may 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 took flight, but was arrested after a brief pursuit in Lake Forest. Inside the car, police said they found a second legally-purchased rifle.

That Crimo’s parents were not exactly nobodies made the shooting even more disturbing to 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 one year older than Crimo in school but said he had known the family for years, told The Daily Beast.

Crimo Jr., who lost the race in a two-to-one margin to the incumbent, ran on the slogan “A Person for the People.” A since-removed Facebook profile suggests Crimo’s mother was involved in the world of alternative medicine.

Jeremy Cahnmann, who ran an after-school sports 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 classes. He said that Crimo was just 9 or 10 when he was 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 really quiet, really soft-spoken, never made an issue.”

Several former classmates emphasized to The Daily Beast that Crimo was “quiet”—a “loner” who never really hung out with a group. Heymann, who participated in cub scouts with Crimo in elementary school, said that “something [was] off, something wasn’t right about him” and said he did not know “if he had any friends.”

Another person who was in cub scouts with Crimo said he lost touch with him after middle school, but remembered him as a quiet, soft-spoken skate-park kid.

“He definitely got judged a little for his goth-like image,” the former acquaintance told The Daily Beast. “In Highland Park, it’s not the most typical 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 with the family business. In that sense, he seemed like a normal kid to them.

“He was never a troublemaker” in junior high, the former classmate said, in contrast to other interviewees.

Ethan Absler, another student who was a year ahead of Crimo in high school, insisted the suspect had “behavioral red flags.” Specifically, Absler said, he was very defiant in class, incessantly promoted his music, and was “the type of student where teachers realized that they were going to have to discipline him in another way or be more realistic about his behavior.”

But the former classmate still felt there was “nothing that would indicate 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.”

Photo by MAX HERMAN/AFP via Getty Images

In high school, Heymann added, Crimo started uploading rap songs on YouTube and went by the name of 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 tactical gear and draped in an American flag.

NBC News reported that Crimo had his own Discord channel that was disabled after the shooting—and that he frequented a message board devoted to death, where he posted a beheading video.

Crimo’s posts also showed him wearing a Trump flag like a cape. Another photo of Crimo showed him at a Trump rally, dressed as Waldo. But he also liked a Twitter video of President Biden, 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 did not have many friends in real life, they missed key warning signs.

“I knew that there was something in his head that was messing with him,” said Nodfather, an independent producer who was friends with Crimo for years after meeting him on Discord. “In all honesty, a lot of it was him being self-isolating.”

The former high school classmate who remembered Crimo showing violent content to his peers 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 might be the parade shooter upon hearing that a younger white male suspect was on the loose.

“This is really freaky, but I was telling someone, ‘This has to be someone from Highland Park that I know,’ and one of the first things I thought was Bobby Crimo because of all the stuff he’s done,” she said.

—with reporting by Daniel Brown in Illinois



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