Thaddeus “T.J.” Jimenez — who squandered a multimillion-dollar wrongful conviction judgment by trying to expand the power of his street gang — is back in legal trouble, facing a new gun charge.
Nearly his entire life has been an odyssey through the criminal legal system, a story that’s captured headlines in Chicago for years.
Jimenez was arrested at 13 for a killing he said he didn’t commit. In 2009, at the age of 30, he was exonerated after spending 16 years in prison. And in 2012, he won $25 million in a lawsuit that accused Chicago police detectives of framing him.
At the time, it was a historic verdict. But he threw away his freedom.
In 2015, he and a friend were riding in Jimenez’s Mercedes when he shot a man as his sidekick recorded everything on a cellphone. Eerily, they were blasting a hymn, “Ave Maria,” on the car stereo. Zach Fardon, the U.S. attorney at the time, called the video “barbaric, cruel, disturbing, numbing to watch.”
Jimenez was sentenced to 12 years in federal prison and received the same sentence in state prison — both for gun convictions related to the 2015 shooting.
He told the judge in his federal case that he was broke after going on a spending spree with his lawsuit winnings.
Jimenez has completed his sentence in those federal and state cases, which were served simultaneously.
But now he’s facing new gun possession charges stemming from a Feb. 16 arrest in Homewood.
Police were called to an office building in the south suburb. Jimenez, wearing a ski mask, was pacing in and out of the building, according to a witness who called the cops.
When the officers arrived, Jimenez ran away with his hand on his waistband, they said.
The officers said they stopped him at a gas station and found a loaded, stolen pistol on the route where he ran away. They also said surveillance footage showed him tossing an object where the gun was found.
Cook County Judge Luciano Pacini Jr. ordered Jimenez detained, saying, “electronic monitoring is not given to a person who is violent in nature and cannot follow orders.”
Jimenez is in the custody of the Illinois Department of Corrections for a violation of his parole in the 2015 shooting case, an official said. Jimenez couldn’t be reached for comment.
His first lawyer in the Homewood gun case, Steve Greenberg, wouldn’t talk about the case. Neither would the Cook County public defender’s office, which took over Jimenez’s legal representation on April 27.
Jimenez, 47, was the subject of a 2019 podcast produced by the Chicago Sun-Times and WBEZ called “Motive.” He declined to be interviewed for the podcast, which, through family members, his lawyers and others, explored his tragic story.
People who knew him said he spent his wrongful-conviction fortune on his gang, the Simon City Royals, and recruited new members on the West Side, rewarding them with trips, money and luxury cars in return for loyalty to him. In the corner of West Humboldt Park where his recruits lived, gang-related shootings surged, the podcast found.
Earl Casteel, the man Jimenez shot in 2015, won a $6 million judgment in a lawsuit against Jimenez for the bullet wounds he suffered to his legs. But Casteel and his family never collected the money. Casteel killed his wife and himself in 2021.
Jose Roman, the friend riding with Jimenez when he shot Casteel, has also served a prison sentence in connection with the 2015 shooting. He’s back in federal custody after a judge found he violated the conditions of his parole.
The violations included running a red light on a motorbike and speeding away from police in 2024 in Prospect Heights. He also repeatedly contacted a woman he was supposed to stay away from. He was accused of pistol-whipping her, federal prosecutors told a judge.
In January, the judge sentenced Roman to two years in federal custody. He’s living in a halfway house in the suburbs, records show.
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Click here to read the Sun-Times April 16, 2017, Watchdogs investigation of Thaddeus “T.J.” Jimenez.