Man who used $25 million settlement to rebuild Chicago gang is going back to prison

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CHICAGO -- A gang leader who used his $25 million award from a wrongful murder conviction lawsuit to rebuild his street gang is headed back to prison, a federal judge ruled Thursday.

U.S. District Judge Harry Leinenweber sentenced Thaddeus Jimenez to more than nine years in prison on weapons charges -- just five years after Jimenez successfully sued the city of Chicago and the police department.

Lienenweber handed down the sentence after the court watched disturbing iPhone video shot by Jimenez's co-defendant, 24-year-old Jose Roman.

The video shows the pair sipping grape soda and listening to opera music as they cruise Chicago's Northwest Side in August, 2015, looking for rival gang members to shoot, according to prosecutors.

At one point, Jimenez, 38, spots a man getting out of his car, ex-gang member Earl Casteel, 33, according to the Chicago Tribune.

Casteel greets the pair and appears surprised when Jimenez pulls out a pistol and points it at him.

The cellphone footage shows Jimenez nonchalantly shooting a stunned Casteel in both legs before driving off.

Jimenez and Roman pleaded guilty to federal weapons charges, but will also stand trial in the shooting of Casteel. Roman was sentenced Thursday to just more than seven years in prison after his attorney argued he was "more of a hanger-on."

The Chicago Tribune reports Jimenez, a leader of the Simon City Royals, spent millions on luxury cars for himself and his gang.

He even paid members to tattoo the gang's insignia on their faces and launched a social media campaign to grow his crew, according to the newspaper.

Jimenez was charged at the age of 13 with the 1993 death of a 19-year-old gang member, Eric Morro. In 2009, Jimenez was released from prison after witnesses recanted their testimony.

(Warning: The full video of the shooting contains graphic content)