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Chicago man freed from prison, given $25 million. He spent his second chance rebuilding his old gang

The top was down on Thaddeus Jimenez’s shiny Mercedes convertible and opera music blared on the stereo as he and a gang associate drove around Chicago’s Northwest Side looking for someone to shoot.

Just three years earlier, Jimenez had won a staggering $25 million verdict for his wrongful murder conviction. But instead of building a new life, he used the windfall to rejuvenate his old gang, paying recruitment bonuses, buying guns and fancy cars, and even giving cash prizes to members willing to tattoo their faces with the Simon City Royals insignia.

Cruising the Irving Park neighborhood on that muggy Monday morning in August 2015, Jimenez carried a sapphire blue, custom-plated pistol and had Gucci luggage bags crammed with extra ammunition stowed in the back seat, court records show. His passenger, Jose Roman, held a .22-caliber Mossberg semiautomatic rifle at his side as he filmed their travels with his iPhone.

Shortly after 11 a.m., Jimenez pulled the Mercedes up to an ex-gang member who knew the two men and greeted them warmly. As the camera rolled, Earl Casteel, 33, was startled to hear Jimenez threaten him.

“Why shouldn’t I blast you right now?” Jimenez declared.

“Blast me, n—-?” Casteel replied, according to a transcript of the video in court records. “You my brother, man! I ain’t got nothing against you.”

Without hesitation, Jimenez nonchalantly aimed his pistol at Casteel’s legs and opened fire, shooting him once in each thigh.

“Why would you do that?” Casteel cried out as he fell to the street.

“Shut up, bitch,” Jimenez said before speeding away.

The graphic video recorded by Roman that day is expected to be played publicly for the first time in a federal courtroom on Thursday as both face sentencing for their guilty pleas to a single federal weapons count. Each still faces charges in Cook County criminal court related to Casteel’s shooting.

In a recent court filing, federal prosecutors called the shooting a “uniquely appalling” act even for a city with a national reputation for rampant gang violence. Had Jimenez and Roman not been arrested, they likely would have posted the video on social media, alongside dozens of other clips depicting how Jimenez’s influx of cash had put the Simon City Royals back on the map, prosecutors said.

“(Jimenez) 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,” Assistant U.S. Attorneys Michelle Petersen and Kathryn Malizia wrote.

Jimenez’s zeal for the gang life didn’t end with his arrest. Weeks after Casteel’s shooting, authorities intercepted a six-page letter Jimenez wrote from Cook County Jail decrying “impostors” who had taken his money and assuring his fellow Royals he was still in control.

“When the big dawg is away, the cats will play,” Jimenez wrote in neat printing. “Not a scratch on me, and yes, I’m still running the s—.”

Prosecutors signaled they’ll seek a 10-year prison term, the maximum possible, for Jimenez, while his attorney, Steven Greenberg, sought the minimum sentence, noting that his client had already spent 16 years in prison for a murder he didn’t commit.

Once he was back on the streets, Jimenez had little guidance and quickly squandered what was left of his settlement on “status-enhancing material goods” and other efforts to rebuild his gang, Greenberg said.

“Ironically, the restitution he received for his terrible injuries did not bring healing, it just drew other vultures to pick at his wounds,” wrote Greenberg, who asked U.S. District Judge Harry Leinenweber for a sentence of about 31/2 years.

‘A cornered animal’

Born in 1979 to a working-class single mother, Jimenez was introduced into the gang lifestyle as a young boy by uncles who were father figures but also Simon City Royals gang members. By the time he was 10, Jimenez was skipping school and “dabbling in drugs,” according to Greenberg’s filing. Soon he had amassed a juvenile record of mostly minor infractions.

But that changed when Jimenez was just 13 and charged as an adult in the February 1993 gang-related slaying of Eric Morro, 19, during an argument on West Belmont Avenue. Several witnesses identified Jimenez as the shooter. He was convicted in 1994 and again in 1997 after an appeals court reversed the original conviction on a legal technicality. Ultimately, he was sentenced to 45 years in prison.

Jimenez spent the first several years of incarceration in a state youth facility, where he was repeatedly “jumped” due to his small size and suffered bouts of depression, Greenberg said. When he turned 17, Jimenez was transferred to an adult prison where he was “terrorized on a daily basis” by both other prisoners and guards, he said.

“His response when confronted was that of a cornered animal — he fought back,” Greenberg wrote.

Behavioral infractions kept Jimenez in segregation and without access to a phone or little human contact for long stretches, including once for close to four years, Greenberg said. Overcome with anger, depression and despair, Jimenez’s moods swung wildly from combative to nearly catatonic.

After years writing letters begging lawyers and other advocacy groups to take a look at his case, he finally caught a break in 2005, when attorneys and students from the Northwestern University Bluhm Center on Wrongful Convictions decided to reinvestigate his conviction.

The lawyers uncovered that an alternate suspect, Juan Carlos Torres, had been surreptitiously recorded confessing to the Morro killing by the father of one of the other youths involved in the argument — a recording that was discounted by the police at the time.

After two key witnesses recanted their earlier statements that Jimenez had fired the fatal shots, the Cook County state’s attorney’s office in 2007 agreed to reopen its own investigation. Two years later, prosecutors indicted Torres in Morro’s murder, but he was acquitted by a judge in 2013.

When Jimenez was released, he was hailed in national headlines as one of the youngest murder defendants in the country to ever be exonerated. He was quickly awarded a certificate of innocence that allowed him to recoup nearly $200,000 from the state for his wrongful imprisonment. But it wasn’t until 2012 that a federal jury awarded him the $25 million in his lawsuit against the city and Chicago police — a verdict that still ranks as one of the biggest police misconduct payouts in the city’s history.

At the time, Jimenez’s civil attorney, Jon Loevy, told the Tribune that Jimenez was working at a restaurant and still “trying to acclimate to life without prison.”

“He’s trying to figure out what to do with the rest of his life,” Loevy said.

Burning through his share

The Simon City Royals formed in the 1950s as a predominantly white greaser gang and rose to prominence through a series of turf battles with Hispanic and black gangs on the city’s North Side. The Royals’ influence had waned after many of its leaders were either killed or locked up, and by the time Jimenez was released from prison in 2009, the gang was all but defunct, according to court records.

In his first few years of freedom, Jimenez managed to stay busy with his legal team working on his civil lawsuit. He began dating a woman and had two children with her. But it wasn’t long before problems arose — including run-ins with police and “self-medicating” with illegal drugs to combat symptoms of post-traumatic stress disorder, according to Greenberg.

Court records show Jimenez was convicted in 2012 of felony narcotics possession and sentenced to a year in prison after police searched his home and found three firearms and a bag of psilocybin, the active ingredient in psychedelic mushrooms. In 2014, he and several other gang members were convicted of misdemeanor reckless conduct for donning masks and bandannas over their faces and surrounding vehicular traffic, prosecutors said.

After the huge jury award came in, nearly half went to Jimenez’s civil attorneys, Greenberg said, but Jimenez quickly began burning through his share, buying fancy cars, throwing lavish drug-fueled parties and paying bonds to free associates facing criminal charges from jail.

“His new family became the gang, reconstructed from his childhood memory of his uncles, the kids he had run with before his first arrest,” Greenberg wrote. “They became his crew — for a price — and gave him the self-esteem he had always craved and had never had.”

Police and prosecutors said that to re-establish the Royals as a force in the city’s gang-infested streets, Jimenez paid $50,000 bonuses to new members and offered cash to those who would tattoo the gang’s insignia on their face. He also launched a social media campaign, posting videos on YouTube and Facebook of himself and other gang members brandishing firearms, flashing gang signs and stacks of cash, and threatening violence against police and rival gangs.

One video from November 2014 showed a shirtless Jimenez loading a clip into a pistol and flashing the Royals’ two-fingered hand symbol. The video depicted images of an assault rifle before concluding with a hooded figure aiming a gun at the camera and the sounds of gunfire, prosecutors said.

Jimenez spent millions of dollars on luxury vehicles alone — including a 2011 Range Rover for Roman and a Porsche Panamera for fellow gang member Luis Candelaria, who has since been sentenced to five years in prison for using a gun in a hate crime, according to court records. He also paid $90,000 for the Mercedes he eventually crashed after Casteel’s shooting, prosecutors said.

In September 2013, Jimenez posted $100,000 to bond out another Simon City Royal who was charged in a drive-by shooting that left a teenager paralyzed, according to prosecutors.

Records show that the money Jimenez was spreading around was having an impact. Violent crimes attributed to the Simon City Royals began occurring on a regular basis, including the January 2015 shooting at a West Side gas station that wounded two innocent bystanders and several killings in the Harrison police district that targeted their main rivals, the Traveling Vice Lords.

On a Saturday afternoon in April 2015, six months before Jimenez’s arrest, an admitted Simon City Royal on the payroll walked into a crowded convenience store on West Chicago Avenue, pulled out a .45-caliber submachine gun and jammed it into the ribs of a customer, saying, “I should kill you right here,” according to court records. Tyrell Thomas pleaded guilty to a federal weapons violation and was sentenced last year to nine years in prison.

In all, nearly a dozen members of the Simon City Royals have been charged with state and federal weapons offenses since 2015, an escalation of criminal activity that demonstrates the gang’s rejection of law and order and its “feudal means of self-governance,” prosecutors wrote in a sentencing memo for Thomas’ case.

“Their behavior … promotes an atmosphere of terror that devastates neighborhoods and leads only to increasingly longer prison terms, or death,” the filing said.

‘The ruling government’

On the morning of Casteel’s shooting, surveillance cameras captured Jimenez and Roman loading the Gucci bags of ammunition into the Mercedes behind an apartment building in the 3200 block of West Belle Plaine Avenue, according to the prosecution filing. Jimenez had switched the rear license plate to throw off law enforcement, and the two had portable police scanners with them as they drove.

Riding through the neighborhood in baseball caps and sunglasses, Jimenez and Roman hammed it up for the camera as they sipped from cans of grape Crush soda. As a female singer belted out an aria, Roman explained how opera was their music of choice when looking for targets to shoot, unlike other “wannabe rappin’-ass n—as.”

As the car cruised down Irving Park Road and onto residential streets, the two bragged about shooting gang members and took mock aim at passersby. They yelled obscenities at one woman as she crossed the street, then honked the horn at another motorist and laughed at the reaction.

“Neighbors are scared of us,” Jimenez remarked, according to the transcript. “We are the police around here. We are the ruling government in our own communities.”

After Roman made a crack about the police, Jimenez said the cops “gonna get it too” if they tried to protect citizens from the Royals.

“Y’all bitches better get bulletproof vests and bulletproof helmets,” Roman said.

At one point during their tour, the pair encountered a man driving a white car. Roman yelled out to the man, “What you is? You ain’t (expletive)? All right, this is Royals hood, homie.” After the man drove away without answering, Roman panned the camera back to his hand as he lowered the rifle and said, “Ooh-ee, I got thirsty.”

Moments later, they encountered Casteel, a onetime gang member and friend from the neighborhood who was getting out of his car near Belle Plaine and St. Louis avenues. The video showed Casteel, unarmed and dressed in a black T-shirt, walk up to the driver’s side of the Mercedes and say, “What’s up, folks?”

“To (Casteel’s) palpable shock, and for no reason rooted in reality, the trigger is pulled,” Greenberg wrote in his filing.

The video ended with Jimenez yelling, “Get the f— out of here!” as Casteel, who dropped out of view of the camera, screamed in pain. Prosecutors said Jimenez ran a red light a few blocks away, then drove the Mercedes at speeds up to 70 mph down busy residential and commercial streets with police in pursuit, weaving in and out of oncoming traffic. He lost control and struck a parked car in the 3800 block of North St. Louis Avenue.

Jimenez crawled out of the damaged Mercedes and ran, dropping his handgun before police caught up with him on North Elston Avenue. Roman was arrested near the Blue Line Irving Park station after tossing the loaded rifle in the back yard of a residence, according to prosecutors.

Casteel needed steel rods to repair fractures to both legs and spent months in physical therapy learning to walk again, according to his lawyer, Kevin O’Brien. He later filed a lawsuit against Jimenez and was awarded a $6.3 million judgment in December in Cook County Circuit Court. O’Brien said he’s currently trying to track down any assets Jimenez may have left.

In his letter to his soldiers from the county jail, Jimenez made no mention of Casteel’s shooting or the mayhem he’d caused that day. But he said being back behind bars would not deter him from his goal to keep the Royals on top. In fact, he implied he was back where he belonged.

“If any of you know anything about me at all, you should know this is where I came from,” Jimenez wrote. “This is where I was created. This is my home.”

jmeisner@chicagotribune.com

Twitter @jmetr22b