Chicago, IL – Joseph Cipolla Jr. allegedly tricked individuals into overpaying for vehicles and aircraft and defrauded the government for pandemic relief funds. A judge is set to sentence Cipolla on Friday in connection to a variety of fraud schemes. Prosecutor’s court filings indicate they are seeking up to 10 years for Cipolla’s crimes.
Cipolla’s fraudulent activities, detailed by the U.S. Attorney’s Office in Illinois, include failing to file federal income taxes for six consecutive years. His schemes involved defrauding the Small Business Administration for pandemic relief funds by falsely selling cars and planes at inflated prices. Cipolla’s plea agreement discloses a request for a seven-year sentence, contrasting with prosecutors’ plea for a sentence of up to 10 years.
According to Assistant U.S. Attorney Timothy J. Chapman, swindling was an ingrained element of Cipolla’s character, as evidenced by his tattooed Latin phrase of “Caveat Emptor” meaning “Buyer Beware.” The ill-gotten proceeds funded Cipolla’s opulent lifestyle replete with luxury cars, a lavish mansion, and support for drug addictions and gambling habits. Records show that Cipolla pleaded guilty in November after facing accusations of tax evasion and mail fraud, leading federal prosecutors to request a nearly 10-year prison term, juxtaposed by the defense’s plea for seven years.
Cipolla’s extensive criminal history, outlined in a sentencing memorandum, spans 17 convictions across four states. The Chicago Tribune detailed accounts of victims, such as Dion Antic, defrauded by Cipolla through fraudulent transactions. The newspaper also reported on the mysterious death of Jeffrey Fox, who tragically perished in a fall from Cipolla’s apartment balcony.
Details from Chapman’s sentencing memorandum outline Cipolla’s methodical evasion of paying federal taxes for five consecutive years. Further, prosecutors indicate that Cipolla engaged in elaborate schemes to defraud people through the sale of used vehicles and airplanes, with federal authorities estimating a loss of over $300,000 due to these deceptions. Another accusation is the trafficking of stolen aviation parts. Cipolla’s defense lawyer cited a troubled history, including parental gambling problems and adult drug addiction. Despite these challenges, since his 2022 arrest, Cipolla has taken steps towards sobriety, according to his attorney.