Joseph Cipolla Jr. allegedly tricked people into overpaying for cars and airplanes and defrauded the government to receive pandemic relief funds. He used the money from his fraud schemes to buy luxurious items including this nearly 11,000 square-foot house (Cipolla: Chicago Police Department; Image of house: U.S. Attorney’s Office)
Had Joseph Cipolla Jr.’s victims knew of his tattoo, they may have steered clear of doing business with him. Proudly inked on his left arm are the Latin words “Caveat Emptor.”
Translation: Buyer beware.
A judge is set to sentence Cipolla, 40, on Friday after he pleaded guilty to fraud to a slew of fraud schemes. According to the U.S. Attorney’s Office in the Northern District of Illinois, Cipolla failed to file his federal income taxes six years in a row, defrauded the Small Business Administration to obtain pandemic relief funds meant for struggling businesses and tricked people into overpaying for cars and airplanes. The defendant has asked for a sentence of seven years behind bars; prosecutors have asked for up to 10 years, according to court filings.
“For Cipolla, swindling people, businesses and the federal government was never motivated by financial desperation, youthful folly, or a onetime lapse in judgment. It was a lifestyle, fueled by unbridled avarice, that was so infused with his character that he proudly wore the words ‘Caveat Emptor’ tattooed on his left arm,” wrote Assistant U.S. Attorney Timothy J. Chapman in a sentencing memo.
The money from the schemes allowed Cipolla to live in a nearly 10,475 square-foot mansion near Chicago, drive luxury cars and support his drug and gambling habits, prosecutors said. Cipolla’s lifestyle caught up to him in 2022 when prosecutors indicted him on tax evasion and mail and wire fraud charges. He pleaded guilty in November, records show. Federal prosecutors want Cipolla to serve nearly 10 years in prison while his defense lawyer is asking for seven years.
Cipolla has previously has been convicted 17 times in four states, mostly for fraud related charges, starting at age 20, the sentencing memo said. He previously spent time in prison in Michigan and Illinois, according to prosecutors.
The Chicago Tribune, which first reported about the case, interviewed one of Cipolla’s alleged victims. Cipolla allegedly wrote a fake $35,000 cashier’s check to Dion Antic, a Chicago entrepreneur, for a used Corvette. Cipolla was convicted in state court but he still owes Antic restitution.
“He’s like a Talented Mr. Ripley,” Antic told the newspaper. “He’s an arch criminal, and it’s been going on like this for years.”
The Tribune also reported about the death of a man who fell nearly 40 stories to his death from the balcony of Cipolla’s apartment in downtown Chicago in 2017. The man, 46-year-old Jeffrey Fox, had previously been accused of assaulting Cipolla’s now-wife, according to the Tribune. The death was ruled an accident.
According to Chapman’s sentencing memorandum, Cipolla did not pay federal income taxes between 2015 and 2020. He used a relative’s Social Security number to hide his casino winnings and used a family member’s identifying information to generate income from a short-term rental, feds said. The total tax loss to the IRS was nearly $500,000 and about $75,000 to the state of Illinois, prosecutors say.
Then in April 2020, Cipolla submitted false tax documents to reportedly obtain more than $1.1 million in pandemic relief funds.
Prosecutors also say that from 2016 to 2022, Cipolla engaged in a scheme to sell used cars and aircrafts under false and fraudulent pretenses. Cipolla supposedly would lie about the condition of the vehicle which would drive up the price. Other times he just took the buyer’s money and never gave them anything in return. He allegedly did the same thing when selling airplanes. The government gave a “conservative” estimate that he defrauded people out of more than $300,000.
He also was allegedly selling stolen aviation equipment.
“Joseph Cipolla is a habitual con-man and fraudster. Over almost two decades, he has repeatedly defrauded individuals, companies and the federal government. His personal characteristics and criminal history suggest that he is as close to a 100% risk of recidivism as a person can be,” Chapman wrote.
Cipolla’s attorney wrote in a sentencing memo that his client had a rough upbringing with parents who had gambling problems and became addicted to drugs as an adult. But since his 2022 arrest, Cipolla has sobered up, attorney Jack Corfman said.
“He understands that what comes next is both a punishment and an opportunity, an intervention into his life while he was hurtling toward the point of no return,” Corfman wrote. “He has pled guilty and acknowledges the wrongfulness of his conduct and the harm that he wrought.”
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