‘He’s like a Talented Mr. Ripley’: Serial scammer Joey Cipolla faces sentencing for life of fraud

By outside appearances, Joey Cipolla was living large.

The 30-something Chicago businessman had seemingly made a small fortune buying and selling luxury cars and leasing private airplanes. He was living in a 12,000 square-foot mansion in west suburban Bloomingdale with a Lamborghini and Bentley in the driveway. He piloted his own Cessna, spent money like water and gambled thousands of dollars at a time in Las Vegas and at local casinos.

But the luxurious lifestyle was just a mirage, federal prosecutors say. Instead, the real truth about Cipolla was inked on his forearm in a small tattoo with the Latin phrase “Caveat Emptor.”

Buyer Beware.

Cipolla, it turns out, has been a fraud his entire adult life, federal prosecutors say. By the time he was in his early 30s, the Northwest Side native had amassed 17 convictions in various schemes across four states, according to prosecutors.

He’d spent significant prison time in Michigan and Minnesota, but prosecutors said instead of being scared straight, Cipolla doubled down, launching a series of more sophisticated schemes that led to his indictment in U.S. District Court in 2022.

On Wednesday, Cipolla is facing his most significant prison sentence yet, after pleading guilty in November to a multi-pronged scheme: stiffing people on luxury auto sales over eBay, rip-offs in the leasing of aircraft out of DuPage County Airport, and using more than $1 million in fraudulently obtained COVID-19 relief funds to fund his over-the-top lifestyle.

Prosecutors are asking for up to about 10 years behind bars, writing in a recent court filing that Cipolla showed an almost boundless capacity for “cruelty and remorselessness” toward his many victims.

“It was a lifestyle, fueled by unbridled avarice,” Assistant U.S. Attorney Timothy Chapman wrote. “There is no sound reason to believe that Cipolla, once released, will abjure his life of fraud and walk a lawful path to acquire the necessities of life.”

Cipolla’s attorney, meanwhile, has asked for a term of seven years in prison, saying Cipolla finally sobered up while in jail awaiting trial and is bent on turning his life around.

“He understands that what comes next is both a punishment and an opportunity, an intervention into his life while he was hurtling towards the point of no return,” wrote Assistant Public Defender Jack Corfman in a filing last week.

But some of those who have been victimized by Cipolla say the crimes he’s been convicted of only scratch the surface. Over the years, Cipolla has been accused of domestic violence. He’s allegedly assumed the identities of enemies online to wreak havoc on their reputations. One woman filed for an order of protection in Cook County after she said he came to her house threatening to kill her family.

And there was a mysterious incident in 2017, when a man plunged 39 stories to his death from the balcony of Cipolla’s apartment in the Aqua tower on North Columbus Drive. Jeffery Charles Fox, 46, of Evanston, had been accused two years earlier of assaulting a woman who is now Cipolla’s wife. Fox’s death was ruled an accident by the Cook County medical examiner’s office.

Former Chicago restaurateur Dion Antic has made it a side hobby digging into all aspects of Cipolla’s multifaceted deceptions, ever since Cipolla gave him a fake $35,000 cashier’s check for a used Corvette that Antic had advertised on eBay. Cipolla was convicted and sentenced to prison for the fraud, but Antic says he still owes him restitution.

Three years ago, Antic started a Facebook account called “Conned by Joey Cipolla” that now has more than 100 followers. He and other victims in Chicago and elsewhere have since formed lasting friendships over their shared experiences, commiserating through Cipolla horror stories.

“He’s like a Talented Mr. Ripley,” Antic told the Tribune, referring to the 1999 film where Matt Damon plays a con artist who assumes the identity of a shipbuilding heir. “He’s an arch criminal, and it’s been going on like this for years.”

Early trouble

Cipolla’s first fraud conviction came in spring 2005, when he was just 20, court records show. By 2008, he’d racked up 15 convictions in four different states, mostly for purchasing vehicles with bad checks.

Prosecutors said Cipolla was brazen, often continuing to pass phony checks while out on bond for other cases. At one point in 2007, he had 11 pending criminal cases spread out between four states, eventually pleading guilty to most and getting as much concurrent time as possible, according to the recent prosecution filing.

Cipolla wound up serving prison time in Illinois and Michigan before being paroled in 2010. By 2014, he was clear of court supervision, according to prosecutors. But Cipolla’s life of crime was just getting started.

“By no later than 2016, he had returned to the relatively lower-paying grift of defrauding people on individual vehicle sales,” Chapman wrote in his filing. He forged paperwork to fraudulently obtain an FAA pilot’s license, then branched into other, more lucrative schemes, such as fraudulent aircraft sales and rentals, Chapman said.

To accomplish this, Cipolla set up a series of limited liability companies that had proxy ownership. Among them was a company he formed in 2018 called Six North Aviation that kept planes in hangars in the DuPage airport in West Chicago, where they were offered for dry lease, meaning without provision of a pilot or crew, court records show.

One early red flag went unnoticed at first: The registered agent for Six North Aviation was listed in Illinois Secretary of State records as Harry Caray, the late Cubs announcer who died in 1998, court records show.

The agent’s address? 1060 W. Addison St., the location of Wrigley Field.

The Caray stunt was hardly Cipolla’s only use of false identities, however. According to Cipolla’s guilty plea, he also used phony “nominees” to rent the airport hangars and buy planes, set up accounts at casinos using his father’s name to avoid being taxed on winnings, and maintained a slew of phony names on eBay to throw unsuspecting victims and law enforcement off his trail.

Meanwhile, Cipolla was conducting a parallel fraud scheme through a series of businesses that bought and sold used exotic cars, companies with names such as Chicago Muscle Cars LLC and Chicago Exotic Car Collection, according to court records.

Over a period of years, Cipolla advertised the cars on eBay and YouTube, including one of a 1963 “split window coupe” Chevrolet Corvette that included a photo of the rare model taken inside one of Cipolla’s rented airplane hangars.

“This car truly needs to find its rightful owner,” the listing read, according to an FBI search warrant affidavit filed in 2021. “I will only answer serious questions about this vehicle as I do expect some wild ones. This car run(s) and drives like new.”

Cipolla admitted in his plea agreement that he illegally “rolled back” mileage on some of the cars he posted for sale, while other times he accepted payment for vehicles he never possessed or were in much worse shape than advertised.

According to the plea, beginning in 2020, Cipolla also used the aircraft and car companies to apply for more than $1.35 million in fraudulent COVID-19 loans under the Paycheck Protection Program and Economic Injury Disaster Loan relief fund.

A total of $1.18 million was actually disbursed, the plea stated. Cipolla used much of the money to buy his five-bedroom, nine-bathroom home in Bloomingdale, which sold for $1.3 million in July 2020, according to an FBI search warrant for the home. Other federal funds were comingled in bank accounts that Cipolla used to shop at Louis Vuitton, a hair salon, and internet jewelry site, according to court records.

Cipolla also admitted in his plea to failing to file any income tax returns reflecting the windfall, for a total tax loss of nearly half a million dollars.

The scams started to catch up with Cipolla in early 2021, in part due to a falling out with his friend whose name was on the DuPage Airport paperwork, according to court records. After the airport sued him for nonpayment of rent for the hangars, the friend fired off an angry text to an acquaintance complaining about money Cipolla owed them.

“Yea … (expletive)  joke. $1,300,000.00 house and can’t pay either of us the money he owes us,” the text read, according to a copy provided in FBI search warrant materials. “He owes me way more than he owes you and I have a feeling that I will never see a penny of it. I’m so completely (expletive) because I trusted him and I never should have done that. SMH.”

Latest case

After Cipolla was initially indicted on federal tax charges in April 2022, prosecutors asked that he be held in custody due to a number of other factors, including that Cipolla had a history of trying to evade law enforcement, court records show.

When federal agents raided his home in July 2021, Cipolla “attempted to evade the officers by retreating to the roof of his own residence, which required law enforcement officers to talk him off of the roof for Cipolla’s and the officers’ safety,” prosecutors wrote in a motion to deny bond.

Just weeks before his indictment, Cipolla was pulled over after fleeing what he thought was federal law enforcement following him, according to a prosecution filing. In reality, no one was there. Cipolla later admitted he had used cocaine shortly before the traffic stop.

“It hardly needs to be stated that Cipolla’s general penchant for driving vehicles at an extremely high rate of speed puts the public at great risk of harm,” the filing stated. “That risk is only magnified when Cipolla engages in that behavior in a desperate effort to flee from law enforcement (real or imagined).”

Cipolla also continued to engage in fraud, creating yet another limited liability company under the alias “John Ward” to fence stolen avionics equipment shortly after his release on home confinement in July 2022, according to prosecutors.

After Cipolla was hit with a 24-count superseding indictment that fall, prosecutors renewed their motion to revoke his bond due to what they said were repeated violations of the orders. U.S. District Judge Matthew Kennelly agreed, ordering Cipolla during a telephonic hearing on Nov. 29, 2022, to turn himself in to federal marshals at the Dirksen U.S. Courthouse no later than 4 p.m. that day, court records show.

After the hearing, law enforcement was again conducting surveillance of Cipolla, “due to fear that he might attempt to flee,” according to prosecutors.

Agents were watching as Cipolla got into an Uber carrying a large bag and rode to nearby Addison, where he waited until his wife arrived in a separate vehicle “and gave him a hug,” according to prosecutors. Cipolla then got into another vehicle with no license plates and drove west, away from Chicago.

Illinois State Police pulled over Cipolla for driving without plates and on a suspended license. He’s been held without bond since at the Metropolitan Correctional Center.

In asking for a sentence of up to 115 months, Chapman asked Kennelly to take Cipolla’s actions into account.

“Only the quick and diligent work by law enforcement officers prevented him from successfully fleeing the jurisdiction,” he wrote.

Cipolla’s lawyer disputes the conclusion that Cipolla was trying to jump bond, noting he was still wearing his electronic monitor at the time and was heading toward the nearest highway “that one would take to go downtown.”

Corfman said that while Cipolla’s crimes are serious, they involved mostly “arms length transactions” that may have cost victims money but didn’t wipe them out, like in many federal fraud cases.

“This is not a case where someone looked into their bank account to find it empty with no warning, only to find it embezzled by an employee or a friend, who abused their position and relationship to obtain goods,” Corfman wrote in his filing.

Corfman called Cipolla “a man of two worlds,” a loving husband and father who is “plainly smart and hardworking, even if sometimes for the wrong goals.”

In a letter to the court filed late Tuesday, Cipolla apologized for his “downright greedy and selfish behavior.”

“I was selling cars and telling people what they wanted to hear just to make a sale,” Cipolla wrote. “I am sorry to anybody that lost money, and I mean that sincerely.”

jmeisner@chicagotribune.com