CHICAGO -- A gang leader who used his $25 million award from a wrongful murder conviction suit 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 both pleaded guilty to federal weapons charges, but will also stand trial in the shooting of Casteel. Roman was sentenced Thursday to just over seven years in prison after his attorney argued that he was "more of a hanger-on."

The Chicago Tribune reports that 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 paper.

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

The full video of the shooting is below. (Warning: Contains graphic content)