'Exhibit A for gun violence,' judge says in handing down prison for brazen Northwest Side shooting

Gang leader drives around Iriving Park listening to opera prior to shooting. Thaddeus Jimenez and Jose Roman recorded themselves on Roman's iPhone driving in Irving Park prior to the shooting of 33-year-old Earl Casteel on Aug. 17, 2015. The men can be heard listening to opera music, flashing guns, yelling at passers-by and threatening authorities. (U.S. attorney's office)

Thaddeus Jimenez and Jose Roman recorded themselves on Roman's iPhone driving in Irving Park prior to the shooting of 33-year-old Earl Casteel on Aug. 17, 2015. The men can be heard listening to opera music, flashing guns, yelling at passers-by and threatening authorities. (U.S. attorney's office)

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As he was led from the courtroom following his sentencing, Jimenez, wearing a baggy orange jail

jumpsuit and shackled at the ankles, blew a kiss to his girlfriend at the back of the packed gallery.

The on-and-off-again girlfriend, Jessica Taylor, later told reporters that Jimenez's volatile mental state was on view in the video.

"I can see how lost he was mentally," she said. "He wasn't there."

While agreeing the video was disturbing, Taylor said Jimenez had little chance given his jailing as a teen, long stint in prison and then the fortune he reaped after his release.

"He's not like you or I," Taylor said. "He had no guidance. Nobody taught him. ... Nobody gave him any advice. You think about it, you're 13, in jail for 16 years, what are you going to do with that amount of money?"

Jimenez won a staggering $25 million verdict in 2012 for his wrongful conviction in the 1993 gang-related slaying of Eric Morro, 19, during an argument on West Belmont Avenue. Nearly half of the jury award went to his civil attorneys, but instead of building a new life, Jimenez used the windfall to rejuvenate his old gang, buying guns and fancy cars, throwing lavish drug-fueled parties and paying bonds to free associates facing criminal charges from jail. Jimenez quickly began burning through his share.

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.

Records show that the money Jimenez was spreading around was having an impact. Nearly a dozen members of the Simon City Royals have been charged with state and federal weapons offenses since 2015, according to prosecutors.

On the morning of Casteel's shooting in August 2015, surveillance cameras captured Jimenez and Roman loading Gucci bags of ammunition into the Mercedes behind an apartment building in the 3200 block of West Belle Plaine Avenue, according to a 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.

With the top down on Jimenez's Mercedes convertible and opera music blaring on the stereo, he and Roman drive around looking for someone to shoot, the video shows. Wearing baseball caps and sunglasses, Jimenez and Roman ham it up for the camera as they sip from cans of grape Crush soda.

As a female singer belts out Schubert's "Ave Maria," Roman explains how opera is their music of choice when looking for targets to shoot, unlike other "wannabe rappin'-ass n---as." Jimenez is carrying a sapphire blue, custom-plated pistol, while Roman holds a .22-caliber Mossberg semi-automatic rifle at his side.

At one point, the pair encounter a man driving a white car. Roman yells out to him, "What you is? You ain't (expletive)? All right, this is Royals hood, homie." After the man drives away without answering, Roman pans the camera back to his hand as he lowers the rifle and says, "Ooh-ee, I got thirsty."

Moments later, they encounter Casteel, a onetime gang member and friend from the neighborhood who is getting out of his car in the 3500 block of West Belle Plaine. The video shows the unarmed Casteel walk up to the driver's side of the Mercedes and say, "What's up, folks?"

"Why shouldn't I blast you right now?" Jimenez declares.

"Blast me, n----?" Casteel replies, 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 aims his pistol at Casteel's legs and opens fire, shooting him once in each thigh.

"Why would you do that?" Casteel cries out as he falls to the street.

"Shut up, bitch," Jimenez says before speeding away.

The video ends with Jimenez yelling, "Get the f--- out of here!" as Casteel, who drops out of view of the camera, screams in pain. Prosecutors said Jimenez ran a red light a few blocks away, then drove the Mercedes at speeds of 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 backyard of a residence, according to prosecutors.

USA - CT.