In August 2015, Thaddeus “T.J.” Jimenez — a wannabe Chicago gang boss with millions of dollars from a wrongful-conviction verdict — took aim from his Mercedes convertible and shot a man in the legs as “Ave Maria” blasted on the car stereo and an associate caught it all on a cellphone video that went viral.
On Wednesday, nearly eight years later, Jimenez pleaded guilty to aggravated battery and was sentenced to 12 years in state prison, wrapping up the last criminal case he faced.
It was one of Chicago’s longest-standing criminal cases. Of the thousands of people held in the Cook County Jail awaiting trial, the case against Jimenez — who was the subject of season 1 of “Motive,” a Chicago Sun-Times and WBEZ podcast in 2019 — was among the oldest.
He was arrested Aug. 17, 2015, after pulling up to Earl Casteel on Belle Plaine Avenue in Irving Park on the Northwest Side, asking “Why shouldn’t I blast you?” and then shooting him in the legs.
Jimenez and his passenger, a gang pal, were arrested after Jimenez crashed the car — one of many luxury vehicles he bought with the money City Hall paid him — during a police chase.
The podcast examined Jimenez’s life — including his arrest for murder at 13, his exoneration at 30, his award of $25 million in a wrongful-conviction lawsuit and his decision to spend the money on his gang, the Simon City Royals on the Northwest Side, along with a faction of another gang, the Vice Lords, whose members he recruited on the West Side.
The 2015 shooting case was complicated because Jimenez and passenger Jose Roman were hit with both federal and state charges over the same crime.
In 2017, Jimenez was sentenced to 110 months in federal prison and Roman to 87 months after they pleaded guilty in the case to illegal gun possession.
Before sentencing them, U.S. District Judge Harry Leinenweber watched the video Roman made of their car ride and the shooting and declared it “shocking” and “Exhibit A for gun violence.”
Roman later pleaded guilty in Cook County criminal court to aggravated battery and was sentenced to six years in prison. He was paroled last year.
But Jimenez’s Cook County case dragged on. In part, that was because he filed an unsuccessful appeal, arguing that the state charges were unconstitutional because he already had been charged in federal court with the same underlying crime. His lawyer Steve Greenberg argued that this amounted to double jeopardy.
Jimenez’s federal and state convictions will run concurrently. That means he’ll have to serve 12 years from the time of his 2015 arrest. He’ll get credit for the almost eight years he already has spent in jail while awaiting trial. He also could earn “good time” in prison that could shave 15% from his sentence.
In court Wednesday, Jimenez appeared in a tan jail uniform, with his hands shackled.
He politely responded to questions from the judge but chose not to give a statement about the crime.
After the court hearing, Greenberg reflected on his client’s case:
“I think he was already traumatized by being in jail,” Greenberg said. “Going back to the place where you were wrongfully locked up has to be awful. And he’s been struggling for a decade now.
“I don’t think I’ve ever represented anyone who has the history that Thaddeus has, who has the trauma that he has experienced in life. And I don’t think I ever had a situation where someone went back to that life like he did.
“I think he wants to lead a normal life. I think it’s difficult for him to lead a normal life because he’s never been allowed to lead a normal life. But, ultimately when he gets out now — he’s an adult — he’ll be able to find a job. I know he’s got a good support system in place now. He’s got a lovely girlfriend. He’s got kids now.”
As part of Jimenez’s plea deal, prosecutors agreed not to pursue charges he was still facing over gang fights that Cook County sheriff’s officials say he got into in the Cook County Jail.
But Jimenez’s legal troubles will continue in civil court. Casteel, the man Jimenez shot, sued him over the shooting, which left him disabled. In 2016, Casteel won a $6.3 million judgment against Jimenez.
But, in 2021, Casteel fatally shot his wife and killed himself.
Now, his lawyer is continuing to try to collect the judgment on behalf of Casteel’s kids, according to court records.
