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Multimillionaire Chicago gang leader gets more than 9 years in prison

Thaddeus ‘T.J.’ Jimenez had used a $25 million court award in a wrongful-conviction case to build his street gang, the Simon City Royals, federal prosecutors said.

Thaddeus “T.J.” Jimenez. | Cook County Sheriff's Office

A visibly shocked judge sentenced Thaddeus “T.J.” Jimenez on Thursday to more than nine years in prison after watching a cellphone video that showed the multimillionaire-turned-gang leader stopping his Mercedes convertible and shooting a man in both legs.

Jimenez had used a $25 million court award in a wrongful conviction case to help build up his street gang, the Simon City Royals, federal prosecutors said. They played a video of Jimenez blasting opera music while cruising in his Mercedes on Aug. 17, 2015, with two guns in the car. His pal Jose Roman recorded their conversation as Jimenez boasted about his gang.

“We are the police over here,” Jimenez said of the Irving Park neighborhood.

Jimenez pulled up to Earl Casteel on the street and said, “Why shouldn’t I blast you right now?” Then he shot him. “Why would you do that?” Casteel said, and Jimenez responded, “Shut up b—-” and drove off. Minutes later, he crashed his car while speeding from police officers and was arrested.

“This is Exhibit A for gun violence,” U.S. District Judge Harry Leinenweber said during the hearing.

“Watching that was really difficult,” he said. “It was shocking.”

The judge sentenced Jimenez to 110 months in prison — slightly less than the statutory maximum of 120 months. Roman got an 85-month sentence. They both pleaded guilty to federal gun charges.

In Cook County Criminal Court, they face other charges related to the shooting.

At a news conference at the federal courthouse, U.S. Attorney Zachary Fardon called the 2015 shooting “cruel and barbaric.”

“I think that video speaks for itself. I hate it because I worry that it’s going to cause further reputational damage to a city that I, and I hope most of you, love and care deeply about. He is not at all reflective or representative of who we are or how we live in this city,” Fardon said.

Jimenez’s case is unique because he recruited members to his gang by spending lavishly on them with the proceeds of the huge settlement he received from the city in a wrongful-conviction lawsuit. He bought Roman a Range Rover and drove fancy cars like the $90,000 Mercedes and a pair of Lamborghinis, prosecutors said.

Jimenez, now 38, was in prison for 16 years after he was convicted at 13 for the fatal shooting of a 19-year-old man in 1993 on the Northwest Side. He was freed in 2009 after his conviction was overturned.

Jimenez received a $25 million settlement and kept about half of it after paying his lawyers. But his criminal defense attorney, Steven Greenberg, said he burned through the money, which is now gone.

Leinenweber explained that he didn’t sentence Jimenez to the maximum because of the trauma he experienced in prison as a youngster. But the judge didn’t mince words about the seriousness of the crime.

“This is one of the most flagrant violations of human rights that I can conceive of,” he said, noting that police are fighting against a tide of violence in which more than 4,300 people were shot last year in Chicago.

Leinenweber also pointed to efforts by the city to raise the prison sentences of people caught with illegal guns.

Roman, 24, was free on bond in two gun-possession cases filed against him in 2014 when he was arrested with Jimenez in the 2015 shooting, prosecutors said.

He was able to post $35,000 — 10 percent of bonds set at $250,000 and $100,000 each — to be released in those 2014 weapon cases. The bonds were revoked when he was arrested in the 2015 shooting, court records show.

Roman addressed the court before he was sentenced, saying, “I would like to apologize to the guy who was shot.”

Jimenez declined to make a statement.

Greenberg acknowledged the horrific nature of the shooting but emphasized that “the prison system was his upbringing” and “he doesn’t know any better.”

“The money didn’t make the injury go away,” he said.

At Greenberg’s suggestion, the judge recommended mental-health treatment for Jimenez.

Jimenez’s girlfriend, Jessica Taylor, said after the hearing that they’ve dated for about six years. Jimenez, dressed in an orange jail uniform with his legs shackled, blew a kiss to her as he was led out of court.

“He has trust issues,” Taylor said. “He doesn’t trust anybody, especially law enforcement. I would imagine if they’ve been against you your whole life, there’s no respect for someone who put you away for 16 years for something you didn’t do.”

But she added: “I know he’s highly regretful of everything.”

Contributing: Jon Seidel