But behind the scenes, the Crimo family was in turmoil. Police reports show that officers were regularly called to their home for domestic disputes between Crimo and his wife, and in 2019, police briefly seized a collection of knives after then-18-year-old Bobby threatened to “kill everybody.” More recently, after the once-bustling deli closed, the family appeared to be in dire financial straits, with foreclosure cases proceeding on both homes they owned and Bob Crimmo telling a judge several weeks ago that he was on food stamps. In the wake of the tragedy, the tight-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 Crimmo — the son of a well-known local figure beloved by his regulars who had even run for mayor several years ago. The elder Crimo faces scrutiny in part because he supported a permit that allowed his son to buy 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 violent images in music videos Bobby posted online, or why Crimo would have sign the gun permit application. “To be so irresponsible and walk away is scary to me,” said longtime Highland Park resident Barbara Medina, who often shops at the deli and marched in the parade when the shooting happened. “It’s a shock that anyone in your town would come and do this in their own community.” Crimo did not respond to CNN’s requests for comment, but in an interview with the New York Post, he said he had no idea Bobby was planning 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’m going to stay here, I’m holding my head up, because I didn’t do anything wrong,” he declared.
The police called several times to the family’s home
More than a dozen Highland Park residents who knew the gunman or his family spoke to CNN about his upbringing as they tried to come to terms with how their town 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 growing 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 haven at night. Regulars remembered the elder Crimo as a gregarious, generous presence who let customers waiting with paychecks buy food on credit and who seemed to man 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 of his customers and their regular orders.
Crimo could be eccentric: Once, a friend said, he competed with another local restaurant owner to see which business could last the longest without replacing a light bulb — until both establishments were almost completely dark.
Crimo’s store closed after 7-Eleven bought the White Hen Pantry chain. But Crimo reopened in a new location under his own name, and his loyal clientele followed.
However, 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 Pesina, would have heated arguments at the deli, even in front of customers.
“It was uncomfortable for people,” the friend said. “I remember thinking, if these are the public arguments, I can only imagine the private ones.”
Police reports released this week show the couple’s arguments continued behind closed doors. In the six years since the deli opened, officers have been called to their home at least a dozen times to settle domestic disputes or respond to allegations that one or the other was drunk.
In one 2010 incident, Crimo claimed Pesina had “struck him on the left forearm with a screwdriver” — before she resigned once he arrived at the police station — and in another, he claimed she hit him in the head with a shoe.
“He threatens to call the police on every fight,” Pessina wrote in a handwritten witness statement. “He says he wants the police to think I’m crazy.”
There is no record that any of these incidents led to criminal charges against either Crimo or Pesina.
The two split up at some point, according to friends, with Pesina living in their home in Highland Park and Crimo moving into his father’s home in nearby Highwood. Bobby lived in both houses over the years.
Pessina also had another brush with the law: In 2002, when Bobby was nearly two years old, she was arrested for child endangerment after she left him in a locked car in a Toys-R-Us parking lot for about 27 minutes one day 79 degrees with the windows rolled up, according to court documents. Pessina pleaded guilty to misdemeanor child endangerment and completed one year of court supervision.
Pessina did not respond to CNN’s requests for comment. Her attorney at the time, Steven Lunardi, said she admitted she was wrong.
Jeremy Cahnmann, who taught Bobby and his brother in a rudimentary 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,” she said. Bobby was “always the kid there at the end that didn’t get him.”
Former classmates describe the suspect as withdrawn and strange
At school, Bobby kept to himself, with the future gunman’s former classmates describing him as a strange, soft-spoken kid who showed little interest in class, school activities or his peers. But he explored a different side of his persona with rap songs and music videos he posted online — some of which included disturbing images.
Molly Handelman, who attended middle and high school with Bobby, described him as a “very quiet” guy. “When he spoke, he was very soft-spoken. He never seemed aggressive,” 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 that he wasn’t interested in 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 high school. “He was making YouTube videos all the time,” the classmate said, “DIY videos on how to hold a skateboard or change a wheel, things like that.”
But in high school, the former classmate said, Bobby became more insular and aloof. “He was always alone,” he said. “No one seemed to be trying to befriend him.”
According to a school district spokesperson, Bobby stopped attending Highland Park High School in 2016, after his freshman year. It is unclear if he went to another school after dropping out.
In recent years, Bobby has revealed a stronger 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 “Wake Up the Rapper,” uploaded his music to several major streaming outlets and a personal website.
In a video titled “Are you Awake”, Bobby sports colorful hair and face tattoos and declares, “I just have to do it. It’s my destiny.” The video shows an animation of a Bobby-like stick man in tactical gear, performing an attack with a rifle.
In another video, a similar cartoon character resembling Bobby is shown lying face down on the ground in a pool of his blood, surrounded by police officers with guns drawn. And in a third, Bobby is seen wearing a helmet and tactical vest and firing bullets into the floor of a classroom.
Economic struggles took their toll
As Bobby struggled in school, his father’s business was also having trouble staying afloat. Regular customers said they noticed more of the store’s shelves were empty and the hours it was open to shrink. In conversations with friends, Bob Crimo complained about a downturn in business, rent increases and fees he said he had to pay to the city. In 2018, Crimo came up with a solution: running for mayor of Highland Park. People who knew him said they were puzzled as to why he would launch a quixotic campaign against the 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 didn’t appear to be actively campaigning, and it’s unclear how seriously he took the fight. State records show Crimo received no campaign donations other than a $560 loan from himself, which he spent on yard signs. In the end, Rotering won 72% of the vote in the April 2019 election, soundly defeating Crimo. In another blow, Crimo’s deli closed at the same time. Google Street View photos show that while the store had a large “Bob Crimo for Mayor” poster hanging in the window in late 2018, as of September 2019, the storefront was empty and vacant. According to court documents, the shop was under 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 default lender in March 2019 after Crimo failed to appear in court. It is unclear whether the debt was ever paid.
Gun license granted despite ominous threats
Around the same time, Bobby began to exhibit more disturbing behavior. In…
