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HIGHLAND PARK, Ill. — A portrait of Robert “Bobby” E. Crimo III as a mysterious and music-obsessed loner began emerging Tuesday, a day after he was arrested in the wake of a mass shooting at a July Fourth parade that left seven dead and traumatized an affluent Chicago suburb.

Crimo, 21, who attempted to disguise himself by wearing women’s clothing during the deadly rampage, aspired to be a rapper and his music got darker and more delusional as he got older and relationships with his parents and a girlfriend frayed, former friends said.

“He was in his own world,” said 22-year-old Nick Pacileo.

“There were a lot of red flags,” added another former Highland Park High School classmate, who asked not to be identified.

Pacileo said he and Crimo bonded over skateboarding and were friends from eighth through 10th grade. He used words like “timid” and “quiet” to describe Crimo’s personality. He said the suspected rooftop sniper never talked about guns and would “zone out a lot.”

Nick Pacileo in Highland Park, Ill., on July 5, 2022.
Nick Pacileo in Highland Park, Ill., on Tuesday.Safia Samee Ali / NBC News

But when Crimo turned 18, around the time he broke up with his girlfriend, his personality changed, Pacileo said.

“Bobby was depressed,” Pacileo said. “He also went off the deep end after he broke up with his girlfriend a few years ago.”

Crimo was obsessed with her, he said, and instead of therapy he turned to drugs.

“He definitely thought there was a border in the mind that needed to be broken through the mind,” he said. “Very third-eye type of stuff that kind of goes along with the psychedelic rap and drugs.”

Crimo also had a strained relationship with his parents, who struggled to make ends meet in the ritzy suburb, Pacileo said.

The suspect’s mother declined to discuss her son when an NBC News reporter approached her for comment.

“Get off my property,” she said outside her home before hopping into a black SUV.

Police reported Tuesday that in April 2019 they were notified after Crimo threatened to take his own life. They also received reports in September 2019 from family members saying, “Crimo was going to kill everyone.”

“At that time, there was no probable cause” to arrest Crimo, said Deputy Chief Christopher Covelli of the Highland Park Police Department. Multiple knives were confiscated, as well as a sword and a dagger, but he didn’t have firearms, Covelli said.

“Everybody knew Bobby was off, but he just — he never actually gave signs that he was capable of that degree of violence in my opinion,” Pacileo said.

Crimo “scared me because of the all the violent things he posted,” said the former classmate who asked not to be identified. “His rap and lyrics were very violent and just weird and he kind of scared me.”

Also, Crimo was constantly in trouble with his teachers. “You always saw him wandering the hallways,” the ex-classmate said.

One reason Crimo kept running afoul of his teachers is because he spent more time promoting his music than he did on his studies, said Ethan Absler, who also attended Highland Park High School.

“He was disruptive in class trying to promote his music — distracting people, asking people to check out his SoundCloud,” said Absler.

Crimo also put stickers promoting his music all over the school, Absler said. But by the end of their sophomore year in 2017, Crimo was gone.

“When he left Highland Park High School, it was my understanding he left to pursue music,” Absler said. “Then reports of him going to this school for troubled children came out as well.”

The school Crimo is rumored to have attended is North Shore Academy, which is also located in Highland Park.

“We have received several requests for information from the media inquiring as to whether or not Robert Crimo III attended North Shore Academy,” the school’s superintendent, Kurt Schneider, said. “The information being reported is inaccurate. He never attended North Shore Academy.”

Absler said he lost touch with Crimo after that. And then, on Monday, Crimo resurfaced — this time as a suspected mass shooter who terrorized his home town.

“I slapped my knee and I said, ‘I know that kid!’” Absler said, when asked what he was thinking when he learned Crimo was in custody. “I just couldn’t believe it. It’s just chilling to know you met somebody, walked in the same halls, we were in the same gym class one year. In this age of school shootings, it makes you wonder how close was I or any of my peers to it at school?”

“His YouTube has always been like red flags and scary,” the ex-classmate said. “He would rant about violent stuff on there.”

Crimo, the ex-classmate said, was “a believer of nothing. Like nothing, no faith, nothing.”

At the same time, Crimo also posted racist rants on Snapchat “to the point where I unfollowed him on Snapchat,” the ex-classmate said.

Pacileo said he wasn’t surprised by the latest revelation that Crimo disguised himself by dressing like a woman.

“That doesn’t surprise me because when Bobby puts his mind to doing something he goes all out and will do anything to make it happen,” Pacileo said. “I think it was like years of trauma, psychedelic drug abuse, you know, that just had him seeing a version of reality that was not ours.”

Safia Samee Ali and Natasha Korecki reported from Highland Park, Illinois, and Corky Siemaszko from New York City.

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