The deli quickly became a popular local spot: a hangout for teenagers, a friendly neighborhood gathering place, and a stop for an affordable, delicious lunch.
But behind the scenes, the Crimo family was in turmoil. Police reports show officers were regularly called to their home because of domestic disputes between Crimo and his wife, and in 2019 police briefly confiscated a collection of knives after then-18-year-old Bobby threatened to “kill everybody.”
Most recently, after the once-bustling deli closed, the family appeared to be in dire financial straits, filing foreclosures on both homes they owned, and Bob Crimo told a judge a few weeks ago that he was on food stamps.
In the wake of the tragedy, the close-knit community of Highland Park is reeling and trying to make sense of a massacre with no apparent motive. Locals said it was even more shocking that the shooter was Bobby Crimo, the son of a well-known local man beloved by his regulars who even ran for mayor a few years ago.
The elder Crimo faces 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 understand how the family could have missed warning signs, including images of violence in the music videos Bobby posted online, or why Crimo signed on the gun permit application.
“To be so irresponsible and to give up is mind-boggling to me,” said Barbara Medina, a longtime Highland Park resident who often shopped at the deli and marched in the parade when the shooting happened. “It’s a shock that it’s somebody in your town that can come in and do this to their own community.”
Crimo did not respond to CNN’s requests for comment, but said in an interview with the New York Post that he had no idea that Bobby was preparing to carry out the shooting and that he was not responsible for his son’s actions.
“I’ve been here all my life and I’ll stay here with my head held high because I’ve done nothing wrong,” he declared.
The police regularly called the family’s 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 understand how their city 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 father’s store growing up. His father operated the White Hen Pantry, a franchise of a local chain store that became famous for its sandwiches.
In an affluent coastal suburb where most shops closed early, the White Hen Pantry was open 24 hours, giving teenagers a safe place to hang out at night. Regulars remembered the elder Crimo as a gregarious, generous presence who allowed customers waiting for a paycheck to buy food on credit and who seemed to man the counter at all hours of the day or night.
Locals describe 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: Once, a friend said, he was competing with another local restaurant owner to see which business could go the longest without changing light bulbs — until both shops were almost completely dark.
Crimo’s store 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. A longtime customer and friend of Crimo’s, who asked to remain anonymous to speak candidly about the family, recalled that he and his wife, Denise Pessina, would have heated arguments at the deli, even in front of customers.
“It was embarrassing for people,” the friend said. “I remember thinking that if these are the public arguments, I can only imagine the private ones.”
Police reports released this week indicate that the fights between the pair continued behind closed doors. In the six years since the deli opened, police have been called to their home at least a dozen times to resolve domestic disputes or respond to allegations that one or the other was intoxicated.
In one 2010 incident, Crimo claimed Pessina “struck him on the left forearm with a screwdriver” – before giving up after he got to the police station – and in another he claimed she hit him on the head with a a shoe.
“He threatens to call the police on any argument we get into,” Pessina wrote in a handwritten witness statement. “He says he wants the police to think I’m crazy.”
There is no evidence that any of these incidents resulted in criminal charges against Crimo or Pesina.
The two separated at some point, according to friends, with Pessina staying at their home in Highland Park and Crimo moving into his father’s home in neighboring Highwood. Bobby has lived in both homes over the years.
Pessina also had another brush with the law: In 2002, when Bobby was almost two years old, she was arrested for child endangerment after allegedly leaving him in a locked car in a Toys-R-Us parking lot for about 27 minutes into a 79-degree day with the windows rolled down, according to court documents. Pessina pleaded guilty to malicious child endangerment and served one year of court supervision.
Pesina did not respond to CNN’s requests for comment. Her attorney at the time, Stephen Lunardi, said she admitted she had made a mistake.
Jeremy Kahnman, who coached Bobby and his brother in an after-school sports program, said the boys stuck in his memory because their parents almost never picked them up on time.
“I remember talking to the teachers at the school about how disengaged the parents were,” he said. Bobby was “always the kid at the end who didn’t get picked up.”
Former classmates described the suspect as withdrawn and strange
At school, Bobby kept to himself, and former classmates of the would-be shooter described him as a strange, soft-spoken kid who didn’t show much interest in class, school activities or his peers. But he explores another side of his personality with rap songs and music videos he posts online — some of which feature disturbing images.
Molly Handelman, who attended middle school and high school with Bobby, described him as a “very quiet” person. “When he spoke, he was very soft spoken. He didn’t seem aggressive at all,” she said.
Handelman, who has worked with Bobby on class projects several times, said there was “something definitely wrong” with him. “He made it very clear that he didn’t care about the school,” she said.
Another former classmate, who asked not to be named for privacy reasons, said he and Bobby hung out, played video games and skateboarded together in middle school. “He was making YouTube videos all the time,” the classmate said, “DIY videos about how to grip a skateboard or change a wheel, things like that.”
But in high school, the former classmate said, Bobby became more withdrawn and distant. “He was always alone,” he said. “Nobody seemed to be trying to be his friend.”
According to a school district spokesperson, Bobby stopped attending Highland Park High School in 2016, after his freshman year. It is not clear if he went to another school after he left.
In recent years, Bobby has revealed a more raucous side of himself online, posting music videos he apparently made — some of which featured lurid lyrics and animated scenes of gun violence. Bobby, who makes music under the moniker “Awake the Rapper,” has uploaded his music to several major streaming channels and a personal website.
In one video titled ‘Are You Awake’, Bobby has multi-coloured hair and facial tattoos and states: ‘I just have to do it. This is my destiny.”
In another video, a similar cartoon character resembling Bobby is depicted lying face down in a pool of his own blood, surrounded by police officers with guns drawn. And in a third, Bobby is seen wearing a helmet and a tactical vest and firing bullets onto the floor of a classroom.
Financial struggles took their toll
As Bobby struggled in school, his father’s business also had trouble staying afloat. Regular customers say they’ve noticed more of the store’s shelves being emptied and its hours being reduced. In conversations with friends, Bob Crimo complained about a drop in business, rent increases and fees he said he had to pay to the city.
In 2018, Crimo settled on a decision: to run for mayor of Highland Park. People who knew him said they were baffled as to why he would mount what appears to be a quixotic campaign against popular incumbent Nancy Rotering, who was Bobby’s former Cub Scout leader. In a local news profile, Crimo talked about making the city more business-friendly, but he doesn’t appear to be actively campaigning, and it’s unclear how seriously he’s taken the race. State records show that Crimo received no campaign contributions, other than a $560 loan from himself that he spent on yard signs. Rötering ended up winning 72% of the vote in the April 2019 election, defeating Crimo decisively. In another blow, Crimo’s deli closed around the same time. Google Street View photos show that while a large “Bob Crimo for Mayor” poster hung in the storefront in late 2018, by September 2019 the storefront was vacant and empty.
According to court documents, the store was saddled with a mountain of debt: A creditor sued the deli and Crimo in late 2018, claiming it owed more than $764,000. A judge ruled in favor of the creditor in default in March 2019 after Crimo failed to appear in court. It is unclear whether the debt was ever paid.
The gun permit was granted despite the ominous threats
Around the same time, Bobby began exhibiting more anxious…
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