How ‘Real Life Talented Mr. Ripley’ Siphoned Millions Through Car Scams, PPP Loans, and More

A fraudulent mastermind (likened to the notorious character from "The Talented Mr. Ripley") has been revealed after perpetrating a $1.1 million scam to sustain an extravagant way of life, replete with luxury cars, a sprawling mansion, and indulgent hobbies, per Daily Mail. Joey Cipolla, the perpetrator in question, faces incarceration for his extensive deception, having driven high-end vehicles like Lamborghini and Bentley, which were often parked outside his opulent 12,000-square-foot residence in Bloomingdale, Illinois—an upscale enclave outside of Chicago.

In addition to his ostentatious automotive choices, Cipolla possessed his own Cessna aircraft, showcasing his prowess as a pilot, and was recognized for frequenting casinos where he routinely wagered thousands of dollars. Despite his façade as a successful entrepreneur, Cipolla's history paints a different picture—one of consistent fraudulence and deceit. His past transgressions include swindling individuals in luxury car sales on eBay and misappropriating COVID relief funds to acquire his lavish estate.

Federal prosecutors are now seeking a lengthy sentence of 10 years, underscoring the severity of Cipolla's offenses. Dion Antic, a local restaurateur and victim, aptly compared Cipolla to the manipulative protagonist of "The Talented Mr. Ripley" describing him as a seasoned criminal whose activities have persisted over an extended period. Antic likened Cipolla to the cunning protagonist from the 1999 film about a con artist, recounting an incident where Cipolla duped him with a counterfeit $35,000 check for a used Corvette.

Three years ago, Antic created a Facebook group titled 'Conned by Joey Cipolla' to vent his frustrations, attracting over 100 followers. This platform has become a community for Cipolla's victims, forging enduring connections through their shared ordeals. Members of Antic's group believe that Cipolla's anticipated sentence falls short of the accountability he truly deserves. In November, Cipolla confessed to his crimes. Prosecutors seek a ten-year sentence, while his defense aims for seven years. Assistant U.S. Attorney Timothy Chapman condemned Cipolla's greed, expressing doubt about his reform post-release. Cipolla's defense lawyer claims jail time prompted reflection and a desire for lawful living.

Cipolla's extensive criminal record includes multiple accusations. In November, he confessed to his crimes, with prosecutors seeking a ten-year sentence while his defense pushes for seven years. A serious incident in 2017 involved the death of Jeffrey Charles Fox, who fell from Cipolla's Chicago apartment; Fox had a history of assaulting Cipolla's wife. Despite these events, Cipolla was not charged in connection with Fox's death, which was deemed accidental by the Cook County medical examiner's office.

By 2008, Joey Cipolla had 15 convictions across four states for vehicle purchase-related bad check offenses. After serving time in Illinois and Michigan, he was paroled in 2010 and released from court supervision by 2014. Subsequently, Cipolla resumed fraudulent activities around 2016, focusing on individual vehicle sales and later expanding into aircraft sales and rentals at DuPage County Airport as detailed in a filing by U.S. Attorney Chapman.

Cipolla also ran a deceptive car business on eBay, admitting to odometer tampering and misleading customers about vehicle conditions. He leveraged these ventures to fraudulently secure over $1.35 million in Paycheck Protection Program (PPP) loans, intended to support businesses during pandemic lockdowns. Joey Cipolla admitted in his guilty plea to receiving $1.18 million from a government relief program, which he used mainly to buy a lavish five-bedroom home in Bloomingdale. The property was sold for $1.3 million in July 2020, according to FBI records. He also spent the ill-gotten funds on luxury goods from Louis Vuitton and jewelry. Cipolla faced federal tax charges in April 2022, with prosecutors noting his history of evading authorities, including an incident in 2021 where he attempted to escape onto his roof during a raid. 

Before his indictment, Cipolla displayed erratic behavior, including a speeding incident where he feared surveillance by federal agents and admitted to recent cocaine use. Ordered to surrender in November 2022, he was apprehended while trying to flee in a vehicle lacking license plates. He remains detained at the Metropolitan Correctional Center in Chicago. In a letter to the court, Cipolla expressed regret for his deceitful vehicle sales and apologized to those affected by his actions.