Man gets 7 years for stealing identities by posing as a ride-share driver outside Chicago nightclubs

CHICAGO — A man has been sentenced to seven years in prison for stealing people’s credit cards and identities while posting as a ride-hail service driver in Chicago. It’s the second time Gabriel Jackson has gone to the big house for the same scam.

He pleaded guilty to operating a continuing financial crime enterprise in exchange for the sentence from Judge Lauren Edidin, according to court records. Prosecutors dropped 25 other felonies in their plea deal, including multiple counts of wire fraud and identity theft.

Jackson had been off parole for about a week when Chicago police arrested him for resurrecting the scam in November 2021. Cops said he had 32 credit cards belonging to 32 different people in his car when they took him into custody.

Prosecutors said Jackson typically preyed on people who were waiting for rides outside nightclubs, mostly downtown and in Wrigleyville.

The case that ended his latest round of criminal activity began when a couple from out of town got into his car outside Spy Bar, 226 West Ontario, around closing time on November 13, 2021.

Jackson told the couple that they were in the wrong car but offered to let them pay him directly for a ride to their destination in Lincoln Park. When they arrived, Jackson scanned a credit card from each victim on his phone and had them enter their PINs, prosecutors said.

He told them their banks declined the transactions, and the victims then paid Jackson $15 cash for the ride. They later realized that someone was conducting transactions on the cards they gave to Jackson.

The couple notified police, and CPD’s financial crimes investigators quickly identified Jackson as a suspect based on their knowledge of his rideshare scam history. Cops arrested Jackson during a traffic stop less than six hours later.

Police found a bag containing 32 credit cards inside Jackson’s Chevy Impala, a CPD report said. A card belonging to the man he picked up at Spy Bar was in his pants pocket, the report said.

On the front seat of Jackson’s car, police found a credit card swiper attached to a cellphone that was opened to an app that records PINs, according to the report.

Gabriel Jackson | Chicago Police Department

Among the 32 cards police found in the bag was one that belonged to a man who identified Jackson as the person who posed as a rideshare driver as the victim left a Wrigleyville bar on September 16, 2021, police reported.

That victim said a phony Uber driver swiped his card on a phone and told him to enter the PIN. The driver returned a similar-looking credit card and then used the victim’s card and PIN to withdraw $1,000 from his account at an ATM near Wrigley Field.

Jackson’s seven-year sentence will be reduced by 50% for good behavior. After receiving credits earned while in custody, he is expected to be paroled on March 30, 2026.

Earlier ride-share scam

Jackson’s first incarnation of the ride-share scam ended in August 2017 when prosecutors charged him with 23 counts of operating a continuing financial crime enterprise and identity theft.

The mechanics of the ruse were the same: he asked bar-hoppers who got into his car to provide a debit or credit card, which he swiped on a phone before asking the victims to enter their PIN.

Then, Jackson would return a similar-looking debit card that did not belong to the passenger. After the victim got out of his car, Jackson drove to an ATM and withdrew cash using the victim’s actual card and the PIN data that they entered, police said.

Jackson picked up passengers around nightlife districts in the 1st, 18th, 14th, and 19th police districts, which stretch from Uptown to the Near South Side and include the Bucktown and Wicker Park areas. He listed a home address in Lakeview East at the time.

Months later, he was arrested again to face additional charges for allegedly operating the same scam while he was supposed to be on home electronic monitoring.

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Tim Hecke is CWBChicago's managing partner. He started his career at KMOX, the legendary news radio station in St. Louis. From there, he moved on to work at stations in Minneapolis, Chicago, and New York City. Tim went on to build syndicated radio news and content services that served every one of America's 100 largest radio markets. He became CWBChicago's managing partner in 2019. His email address is