‘A unique combination of greed, intelligence, and remorselessness’: Feds make case for 10-year sentence for Chicago con man

A federal prosecutor on Wednesday described serial Chicago con man Joey Cipolla as a charmer with an unhealthy obsession with wealth — and he doesn’t care about hurting people to get it.

“(Cipolla) is a unique combination of greed, intelligence and remorselessness, and that makes him profoundly dangerous,” Assistant U.S. Attorney Timothy Chapman said in asking a federal judge to sentence Cipolla to nearly 10 years in prison. “He’s trying to be someone that he is not capable of being unless he steals the money to pay for it.”

Cipolla’s attorney, Jack Corfman, is asking for as little as seven years behind bars, arguing Cipolla was addicted to cocaine for much of his fraud schemes and is finally ready to live life on the straight and narrow now that he’s sobered up in jail.

But Chapman said Cipolla’s motive for swindling dozens of unsuspecting victims is simple and has not changed.

“It’s pure greed,’ Chapman said.

Cipolla, 40, pleaded 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 pay for his over-the-top lifestyle.

U.S. District Judge Matthew Kennelly cut Wednesday’s sentencing hearing short because of another commitment, asking the parties to return Friday at 10 a.m.

Cipolla’s federal indictment in 2022 capped nearly two decades of crimes that have lasted virtually his entire adult life. His 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.

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 now Cipolla is likely facing the most serious punishment yet. In a letter to the court filed Tuesday, Cipolla apologized to “anybody that lost money” and said the judge can believe him when he says he’s ready to live a law abiding life.

Chapman, however, said Cipolla’s words lacked “any real acknowledgement that the pain and suffering he inflicted” on his victims went far beyond just financial loss.

One victim from Canada wrote in a letter Chapman read aloud in court that he’s had trouble trusting anyone since he borrowed $35,000 from his parents to buy a 1969 Pontiac GTO that Cipolla had advertised on eBay. Cipolla took the money and the victim wound up with nothing.

“They are human beings,” Chapman said of the people Cipolla had swindled. “Either he doesn’t see it or he doesn’t care, but whatever the situation is, it makes him profoundly dangerous.”

Corfman will get a chance to argue Friday before Kennelly imposes the sentence.