Highland Park gunman’s family was in turmoil for years leading up to parade shooting

In the wake of the tragedy, the close-knit community of Highland Park is reeling and trying to understand a massacre with no apparent motive. Locals said that it was even more shocking that the shooter was Bobby Crimo — the son of a well-known local figure beloved by his regular customers, who even ran for mayor several years ago.

The elder Crimo is facing scrutiny in part because he sponsored a permit allowing his son to purchase firearms before he turned 21, including the gun he used in the shooting. Locals who once lined up for “Nicky D” sandwiches at Bob’s say they can’t comprehend how the family could have missed warning signs, including violent imagery in the music videos Bobby posted online, or why Crimo would have signed the gun permit application.

“To be that irresponsible and signing off is mind-blowing to me,” said Barbara Medina, a longtime Highland Park resident who often shopped at the deli and was marching in the parade when the shooting took place. “It’s a shock that it’s anybody in your town, that they could come in and do that to their own community.”

“I’ve been here my whole life, and I’m gonna stay here, hold my head up high, because I didn’t do anything wrong,” he declared.

Police called to family home several times

More than a dozen Highland Park residents who knew the shooter or his family spoke to CNN about his upbringing, as they tried to piece together how their city had joined the long list of American communities whose names have become shorthand for mass shootings.

By all accounts, Bobby Crimo was a quiet kid, who could be seen running around his dad’s shop as he grew up. His father ran the White Hen Pantry, a franchise of a local convenience store chain that became known for its sandwiches.

In an affluent lakeside suburb where most shops closed early, the White Hen Pantry was open 24 hours, giving teenagers a safe hangout spot at night. Regulars remembered the elder Crimo as a gregarious, generous presence who would let customers waiting on a paycheck buy food on credit, and who seemed to be manning the counter at all hours of the day and night.

Locals described Crimo as “the mayor of Ravinia,” the local neighborhood where the store was located, who knew all his customers and their regular orders.

Crimo could be eccentric: One time, a friend said, he competed with another local restaurant owner to see which business could go longer without replacing any lightbulbs — until both stores were almost completely dark.

Crimo’s shop closed after 7-Eleven bought out the White Hen Pantry chain. But Crimo reopened in a new location under his own name, and his loyal clientele followed.

Still, there were signs of trouble in the family. One longtime customer and friend of Crimo’s — who asked to remain anonymous to speak candidly about the family — remembered that he and his wife, Denise Pesina, would have heated arguments in the deli, even in front of customers.

“It was awkward for people,” the friend said. “I remember thinking, if that’s the public arguments, I can only imagine the private ones.”

Police reports released this week show that the couple’s fights continued behind closed doors. In the six years after the deli opened, officers were called to their home at least a dozen times to settle domestic disputes or respond to allegations that one or the other was intoxicated.

In one 2010 incident, Crimo alleged that Pesina “had hit him with a screwdriver on the left forearm” — before recanting once he got to the police station — and in another, he claimed she hit him on the head with a shoe.

“He threatens to call the police for any and every argument we get in,” Pesina wrote in one handwritten witness statement. “He says he wants the police to think I’m crazy.”

There is no record that any of those incidents led to criminal charges against either Crimo or Pesina.

The two separated at some point, according to friends, with Pesina staying in their Highland Park home and Crimo moving to his father’s home in neighboring Highwood. Bobby lived in both homes over the years.

Pesina had had another brush with the law as well: In 2002, when Bobby was nearly two years old, she was arrested for child endangerment after allegedly leaving him in a locked car at a Toys-R-Us parking lot for about 27 minutes on a 79-degree day with the windows rolled up, according to court documents. Pesina pleaded guilty to misdemeanor child endangerment, and completed a year of court supervision.

Pesina did not respond to CNN’s requests for comment. Her lawyer at the time, Steven Lunardi, said that she admitted having made a mistake.

Jeremy Cahnmann, who taught Bobby and his brother in an elementary after-school sports program, said the boys stuck out in his memory because their parents almost never picked them up on time.

“I remember talking to faculty at the school about how uninvolved the parents were,” he said. Bobby was “always the kid there at the end who didn’t get picked up.”

Former classmates describe suspect as withdrawn and odd

At school, Bobby kept to himself, with former classmates of the future gunman describing him as an odd, soft-spoken kid who showed little interest in class, school activities or his peers. But he explored a different side of his personality with rap songs and music videos he posted online — some of which included troubling imagery.

Molly Handelman, who attended middle school and high school with Bobby, described him as a “very quiet” guy. “When he did talk, he was very soft. He didn’t seem aggressive ever, at all,” she said.

Handelman, who worked with Bobby on class projects a few times, said “something definitely seemed off” about him. “He made it very clear he didn’t care about school,” she said.

Another former classmate who asked not to be named due to privacy concerns said he and Bobby used to hang out, play video games and skateboard together in middle school. “He would make YouTube videos all the time back then,” the classmate said, “DIY videos on how to grip a skateboard or replace a wheel, stuff like that.”

But in high school, the former classmate said, Bobby grew more insular and distant. “He was always by himself,” he said. “No one seemed to try to be his friend.”

According to a school district spokesperson, Bobby stopped attending Highland Park High School in 2016, after his freshman year. It’s unclear whether he went to another school after dropping out.

In recent years, Bobby revealed a louder side of himself online, posting music videos he apparently made — some of which featured ominous lyrics and animated scenes of gun violence. Bobby, who made music under the moniker “Awake the Rapper,” uploaded his music on several major streaming outlets and on a personal website.

In one video titled “Are you Awake,” Bobby sports multicolored hair and face tattoos and declares, “I need to just do it. It is my destiny.” The video shows a cartoon animation of a stick-figure man resembling Bobby in tactical gear, carrying out an attack with a rifle.

In another video, a similar stick-figure cartoon character resembling Bobby is depicted lying face down on the ground in a pool of his own blood, surrounded by police officers with their guns drawn. And in a third, Bobby is seen wearing a helmet and a tactical vest and dropping bullets onto the floor of a classroom.

Financial struggles took a toll

As Bobby was struggling in school, his father’s business was also having trouble staying afloat. Regular customers said that they noticed more of the shelves in the store going empty, and the hours it was open shrinking. In conversations with friends, Bob Crimo complained about a downturn in the business, increases in rent, and fees he said he had to pay the city.

According to court documents, the store was under a mountain of debt: A lender sued the deli and Crimo in late 2018, alleging he owed more than $764,000. A judge ruled in the lender’s favor by default in March 2019 after Crimo failed to appear in court. It’s unclear whether the debt was ever paid.

Gun permit granted despite ominous threats

Around the same time, Bobby started showing more troubling behavior.

In April 2019, according to police reports released by Highland Park, officers performed a wellness check on the 18-year-old Bobby after receiving a report that he had “attempted to commit suicide by machete” a week prior. Mental health professionals handled the episode, officers wrote.

Attorney George Gomez, who is representing both parents, told CNN that “the family denies that there was any issues of suicide at the time,” and stressed law enforcement found “no safety risk.”

Meanwhile, the family’s finances appeared to unravel in recent years. HSBC Bank filed for foreclosure on their Highland Park house, where Bobby had grown up, in December 2019, alleging Crimo, Jr. owed more than $460,000. The case was delayed amid the coronavirus pandemic, and the lender restarted efforts to take possession of the home last year.

In April 2022, a mortgage servicing company filed to foreclose on a second property Crimo owns in the neighboring town of Highwood. The company, NewRez LLC, alleged that he had failed to make payments since July 2020, and owed more than $197,000.

In the Highland Park case, a judge granted Crimo a full waiver of court fees in May after he appeared in person and provided proof that he was receiving food stamps, according to court documents.

Last Thursday — four days before the shooting — Crimo filed a last-ditch motion to block foreclosure of the house, arguing the lender hadn’t given him sufficient notice of being in default or of accelerating the due date for the balance of the mortgage.

Paul Crimo, Bob’s brother, who lives with him and worked at his delis, told CNN he didn’t think the financial stress affected Bobby.

“My brother always made sure his kids always had a roof over (their) head at all times,” he wrote in a text message, adding that Crimo “is a great father.”

Community looks to family for answers

Some of the Highland Park residents who were at the parade when Bobby opened fire said they blamed the father for allowing his son to buy guns.

The elder Crimo “should be held liable for it and responsible for it,” declared Fred Kroll, a three-decade Highland Park resident who attended the parade with his wife and daughter and said he saw multiple people shot dead. “Whether it’s civil lawsuits by the survivors or he goes to jail … he should be punished.”

State officials have poured cold water on the idea of Crimo facing criminal responsibility over the deaths. “There’s not a criminal liability that’s directly attached to vouching for someone else… and they end up doing something terrible like this,” said Eric Rinehart, the Lake County State’s Attorney.

Gomez said the family is “trying to cooperate with all local, state, and federal authorities at the moment.” When asked if he felt there was any criminal wrongdoing on part of his clients, particularly the father, Gomez said, “we take the position that my client, Crimo Jr., did nothing wrong in this case.”

Still, even Crimo’s friends say they doubt he’ll be able to stay in his hometown, or ever open a business here again.

“His kid shot up his hometown, and he’s going to have to come to terms with that action and, honestly, the role he played in his son’s evolution as a person,” one friend said. “It was his son’s name on the news — and that’s his name, too.”