How 25 Million in Chicago Tax Dollars Fueled the Rise of Gang Kingpin

Federal prosecutors are seeking a maximum 10-year prison sentence for Thaddeus “T.J.” Jimenez, who became a multimillionaire in a wrongful conviction lawsuit against the city and went on to become a ruthless Chicago gang leader.

Jimenez has pleaded guilty to possessing a gun illegally in 2015. He and a sidekick, Jose Roman, were riding in Jimenez’s $90,000 Mercedes convertible when they pulled up to Earl Casteel on the Northwest Side, according to a sentencing memo filed Wednesday.

Roman recorded the encounter, in which Casteel pleaded on the cellphone video, “you’re my brother, man. I ain’t got nothing against you.” Jimenez then shot Casteel in each leg. “Why would you do that?” Casteel asked. Jimenez replied, “Shut up, bitch” and drove off.

Chicago Police arrested the men and recovered a gun from each of them after a chase that ended with the Mercedes crashing.

Jimenez, 37, admitted he possessed the .380-caliber pistol he used to shoot Casteel. Roman pleaded guilty to the same charge for possession of a rifle the same day.

Prosecutors are seeking a 10-year sentence for Jimenez and a sentence of about seven years for Roman.

Jimenez 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.

He received $25 million in a lawsuit against the city and spent much of his fortune on his gang, the Simon City Royals, prosecutors said.

He recruited new members and paid them thousands of dollars each to tattoo the gang’s cross symbol on their faces, sources have told the Chicago Sun-Times.

He bought a Range Rover for his friend Roman and put up $100,000 to help a fellow gang member post bail in a drive-by shooting that left a teenager paralyzed.

Jimenez’s stable of expensive cars included Bentleys and Lamborghinis, records show.

The North Side-based Simon City Royals — who previously kept a low profile among Chicago’s violent gangs — are suspected in multiple killings on the West Side, where they moved in on the drug trade in recent years, sources said.

Almost a dozen members of the gang have been charged with state and federal gun crimes since 2015.

In their filing Wednesday, prosecutors said Jimenez’s “nihilism and self-destructive behavior” could be explained by his tragic youth. But his past doesn’t excuse his decision to “glorify and perpetuate violence using funds intended to make him whole.”

He received a “sum that would be truly staggering to all but the wealthiest in this country. He could have used this money in any number of ways — to assist friends and family, contribute to the community, sponsor others wrongfully convicted or simply live in comfort for the rest of his natural life. Instead, he chose to build a gang,” prosecutors said.

In December, Jimenez suffered a major downturn in his fortunes when a Cook County judge awarded Casteel $6.3 million in a lawsuit he filed against Jimenez for shooting him. Last year, Jimenez said in court that he was practically broke.

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Gang leader who won $25M settlement offering $50,000 to new members

A reputed gang leader who won a whopping $25 million verdict just three years ago for his wrongful murder conviction was paying out $50,000 recruitment bonuses along with guns and cars to bring new members into his gang, Cook County prosecutors alleged Wednesday.

Thaddeus Jimenez, 36, who prosecutors allege heads the Simon City Royals gang, was charged in a brazen Monday morning shooting of a former gang member who had refused Jimenez’s recruitment efforts, authorities said.

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From Wrongful Conviction to ‘Gang Kingpin’

Thaddeus Jimenez was 13 when he was convicted of a murder he did not commit.

He served 16 harrowing years of a 45-year prison term before he was exonerated.

He won a record $25 million in a wrongful-conviction suit against the City of Chicago and the detective who framed him.

He used part of that 2012 award to buy at least 14 cars, including a Mercedes convertible, a Bentley, and a Lamborghini.

And, prosecutors say, he began offering $50,000 bonuses, cars, and guns as inducements to recruit members to his gang, the Simon City Royals.

On August 17, Jimenez rolled up in his gray Mercedes to a 33-year-old former gang member who had refused inducements to rejoin. Jimenez allegedly shot the man in the legs with a pricey sapphire-blue .380 automatic pistol—blue, along with white, being the gang’s colors.

A police car that happened to be in the area gave chase and Jimenez was arrested.

Now 36, he is back behind bars, remanded without bail on state assault and weapons charges, unable to free himself despite his millions. He also faces a federal gun charge that can carry 10 years.

Back on the early morning of February 3, 1993, when he was just 13, Jimenez had been asleep in the front room of his grandmother’s apartment when he was awakened by a pounding at the door.

Detectives entered, asking for T.J., as Jimenez was known. He was told to put on his shoes and jacket and then to turn around and place his hands behind his back. He was being led in handcuffs out of the apartment when the grandmother asked the detectives if they could at least tell her why he was being arrested, so she could tell his mother.

“They said, ‘He’s going to jail for murder,’” Jimenez would testify in the civil suit. “I was shocked…I told my grandmother, ‘Wait by the phone in the kitchen. Wait by the phone and I’m going to call you when this is all square and it’s time for you to come pick me up at the police station. Just wait by the phone. I’m going to call you to come get me.’”

At the time, Jimenez had been a member of the “pee wee” division of the Simon City Royals, one Chicago’s few predominantly white gangs. He would recall, “I wanted to be cool. I always wanted to be the cool kid.” He would insist that the peewees did nothing more than walk around and flash gang signs.

But the gang association had apparently helped induce a bad case of tunnel vision in the lead detective after the squad got a call saying that someone named “T.J.” had shot and killed 19-year-old Eric Morro. A check of the gang nickname computer database produced the name Thaddeus Jimenez.

The one eyewitness was a 14-year-old who gave an initial description that bore little resemblance to Jimenez. The boy nevertheless ended up identifying Jimenez as the killer after a prolonged and reportedly terrifying time in a police interrogation room.

The one other witness was a pregnant woman who had been standing some distance away and told the detective she had not seen the killer’s face. She was given a seat in the squad room at a desk on which a photo of the victim had been placed next to a photo of Jimenez. She then viewed a lineup and identified Jimenez as the killer.

Another teen admitted to being with the shooter at the time of the killing, but insisted that Jimenez was not the gunman. The teen said the actual killer was Juan Torres, initials J.T., who subsequently confessed on tape.

All that was ignored as Jimenez was held without bail in a juvenile facility. He was one of the youngest and smallest prisoners. He would recall that he was doubly vulnerable.

“The fact that I was innocent. Number one, because jail is not a place for innocent guys,” he would testify in the civil case. “Two, by my size, my age, my inexperience. I was like a goldfish in a tankful of sharks.”

He went through two years of seemingly endless hearings and continuances before the trial finally commenced.

“I felt like as soon as we went to trial, I was going home,” he would remember. “They was going to prove I was innocent.”

The taped confession by J.T. never reached the courtroom. And, despite the absence of any physical evidence, T.J. was convicted on the basis of the two iffy witnesses. Jimenez was sentenced to 45 years.

When he turned 17, Jimenez was transferred to Stateville, an adult maximum security prison for some of Illinois’s most violent criminals.

“I was the only kid there,” Jimenez would testify. “The inmates controlled the entire prison, every aspect of it. The only thing that the inmates didn’t have was the keys to the front door.”

He went on, “They had control of the telephones. They decided what we ate for dinner. They decided who went to church, who went to gym, who went anywhere…They made every rule… from what time to eat, from what time to get out of your bed…They had a set of rules you had to abide by, and you abided by those rules and not the prison…Their rules were the only rules, plain and simple They made the rules.”

He continued, “They filed down the locks on the doors so they can go in your cell anytime they want. They could just yank the bars open…I can’t sleep under them conditions, when you know these guys can just go in your cell whenever [they] want.”

He said in summary, “I was at the mercy of monsters.”

He had been left with two choices; ask to go into protective custody or join a gang. There was one problem with the former.

“You’re not being protected at all,” he testified. “You think that by going into protective custody you would be protected, but the truth is that place was rampant with other kinds of predators; mainly sexual predators that wouldn’t otherwise survive in general population.”

That left joining a gang. There were next to no other Simon City Royals and he ended up affiliating himself with a Latin gang, his father being Mexican, though his mother was Polish.

“I didn’t fit in with no one there,” he would later say. “I was a joke to them. For one…was my race… Other than that, the fact that I was innocent alone set me aside. You know, I was sticking out like a sore thumb because I am telling them, ‘No, I’m not a murderer, I’m innocent.’”

He continued, “These are guys who are, you know, bragging about it; ‘Man, I’m locked up for killing five people’…and here I am like, ‘Man, I didn’t do anything’…Everybody that knew me say, ‘Yeah, T.J. Oh, that’s the innocent guy. He’ll tell you he’s innocent’…They were looking at me like, ‘You don’t even belong here…You’re not even a real killer.’”
His grandmother died and he was not permitted to attend her funeral.

“My grandmother hit me harder than anything because I kept playing it over and over in my head for years like. ‘Grandma, wait by the phone. I’m going to call you when it’s time for me to go home,’’’ he would testify. “When she was alive, she would go, ‘I’m still waiting by the phone…’ We used to joke like that and it hurt for us to joke, but we had to put a smile on because that was the last time I have ever, you know, been with my grandmother. And we were hoping one day we were going to…”

He ended that sentence there and went on, “She used to tell me, ‘I don’t care how old you are, you’re still going to be my baby…’ But she died, and that hurt me because I never even got to say goodbye. She never got to know me as a man. I was a grown man already, and she never knew what type of person I was. She never got to cook breakfast or let me take her to the store, the stuff that, you know, we would do when I was a kid.”

In 2007, the state’s attorney’s office agreed to take another look at the case. A two-year investigation concluded that Jimenez was indeed innocent.

In 2009, after 16 years, two months and 28 days in prison, Jimenez was freed. He went to work at a Sonic fast-food spot and fathered a baby with a fellow fast-food worker as his wrongful-conviction suit proceeded through federal court.

In 2012, a jury awarded him $25 million. He used some of the cash to post bail after he was arrested for felony drug possession and twice for felony gun possession.

“He was raised, essentially, by the penitentiary system, which, I think, is the equivalent of being raised by wolves,” his attorney, Scott Frankel, said at a court hearing.

Nobody could have been much surprised when he was reported to have gone from the peewee division to the leadership of the Simon City Royals. He was alleged to have used more of the award money to build up the membership with cash and gifts, perhaps a gang first.

On August 17, police in an SUV spotted Jimenez and a reputed gang crony speeding in the Mercedes away from where there had been a report of shots fired. The two were arrested on assault and weapons charges in connection with the shooting of the recalcitrant former Simon City Royals member.

On August 26, Jimenez was also hit with a federal indictment for being a convicted felon in possession of a firearm. He is scheduled to be arraigned on Wednesday.
The federal complaint notes that the gun was a loaded Kimber Sapphire .380 automatic.

The legit manufacturer’s suggested retail price for the pistol is $1,014—as only befits a millionaire gangbanger who might as well have been raised by wolves.

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