CHICAGO — Serial Chicago con man Joey Cipolla was sentenced to nine years in federal prison Friday for what the judge called “an extraordinarily large amount” of schemes to cheat people out of money.

In handing down the 108-month sentence, U.S. District Judge Matthew Kennelly noted that Cipolla had spent time in state prison for similar crimes before, but instead of being deterred he soon returned to scamming people.

“One would think that if Mr. Cipolla had the ability and willingness to control what he was doing — because he obviously has skills — that (his previous prison time) would have been enough. But it wasn’t.”

Kennelly said that was a sign that a lengthy sentence was needed to keep Cipolla “separated from the public.”

“There are people out there that need to be protected from Mr. Cipolla,” Kennelly said. “… It seems like one of those situations where Mr. Cipolla sees opportunities and he takes them.”

In addition to the prison sentence, Kennelly ordered Cipolla to pay $1.6 million in restitution, which includes back taxes he owes to the IRS and state.

Cipolla, 40, pleaded guilty in November to a multipronged 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. He also admitted he failed to file income tax returns for years, cheating the IRS out of hundreds of thousands of dollars in taxes.

In asking for up to about 10 years in prison, federal prosecutors described Cipolla as a smooth talker and charmer, a man with an unhealthy obsession with wealth who 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 at the first phase of Cipolla’s sentencing hearing earlier this week. “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, asked for as little as seven years behind bars, arguing many of Cipolla’s crimes were fueled by a cocaine addiction and that Cipolla is finally ready to live life on the straight and narrow now that he’s sobered up in jail.

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