A man who has twice gone to prison for stealing people’s credit cards and identities while posing as a rideshare driver in Chicago is accused of resurrecting the same scam, victimizing at least six more people, and possessing cards and identification belonging to 14 additional victims.
CWB Chicago has been telling you about Gabriel Jackson’s exploits for nearly a decade, and it looks like we’ll be telling you about him for the foreseeable future.
Chicago police arrested Jackson, 58, early on May 22 in the 300 block of North Wells Street and charged him with felony identity theft after a 38-year-old South Loop man identified him in a photo lineup as the person who picked him up while posing as a rideshare driver on November 15.
The victim climbed into Jackson’s car outside the Hangge Uppe, 12 West Elm Street, around 2:33 a.m. and Jackson allegedly asked for his debit card. The victim handed it over and entered his PIN into a machine operated by Jackson, who then returned a different debit card to him, according to charging documents.
Jackson drove the man to his destination, but prosecutors say he later used the victim’s debit card to make more than $2,000 in unauthorized transactions.
That, right down to targeting a victim outside a nightclub, is exactly what Jackson has been accused of doing over and over since at least 2017.
Prosecutors have said the scam typically starts with Jackson posing as a rideshare driver and picking up people who are waiting for rides outside nightclubs downtown or in Wrigleyville. Jackson would then convince them to hand over a credit or debit card, ostensibly to pay for the ride, then has them enter their PIN into a card reader or phone app. He returned a different card to the victim and used the stolen card information to make unauthorized purchases or withdrawals.
Initially, prosecutors did not seek to detain Jackson after his May arrest. But detectives continued building cases, and prosecutors eventually secured a 25-count grand jury indictment charging Jackson with continuing financial crime enterprise, theft by deception, wire fraud and identity theft, according to court records.
The charges allege a similar pattern of crimes between November 15 and May 20 involving six victims who fell for the rideshare scam with losses estimated between $10,000 and $100,000, according to the indictment. The victims were allegedly picked up in Jackson’s fake rideshare on November 15, December 18, December 21, twice on March 15 and again on May 20.
When police arrested Jackson on May 22, he allegedly had credit cards, debit cards and identification documents belonging to 14 people other than the known rideshare scheme victims, according to the charging papers.
After the indictment was returned, prosecutors sought to detain Jackson, pointing to his previous convictions for operating a continuing financial crime enterprise under the same basic scheme. Judge Domenica Stephenson granted the detention request, according to court records.
Jackson received a seven-year prison sentence in 2023 after pleading guilty to running the same rideshare scam in which prosecutors said he stole victims’ credit cards and identities.
He had been off parole for about a week when Chicago police arrested him for allegedly resurrecting the scheme in November 2021. Police said they found 32 credit cards belonging to 32 different people in his car.
That spree began November 13, 2021, when a couple from out of town got into Jackson’s car outside Spy Bar, 226 West Ontario Street, around closing time. Jackson told the couple they were in the wrong car but offered to let them pay him directly for a ride to their destination in Lincoln Park, prosecutors said. When they arrived, Jackson allegedly scanned a credit card from each victim on his phone and had them enter their PINs. He then told them their banks had declined the transactions, prosecutors said. The victims paid Jackson $15 cash for the ride. They later realized someone was making unauthorized transactions on the cards they had handed over.
The couple notified police, and CPD’s financial crimes investigators quickly identified Jackson as a suspect based on their knowledge of his previous rideshare scam history. Officers arrested him during a traffic stop less than six hours later. Police found a bag containing 32 credit cards inside Jackson’s Chevy Impala, according to a CPD report. A card belonging to the man he picked up at Spy Bar was in Jackson’s pants pocket.
On the front seat, police found a credit card swiper attached to a cellphone. The phone was open to an app that recorded PINs, according to the report.
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