Updated 4:41 p.m
A judge Thursday sentenced the boss of one of Chicago's most violent street gangs to 40 years behind bars, saying the Hobos boss had used his many talents "to advance the cause of evil."
Gregory "Bowlegs" Chester, 40, led the South Side gang that prosecutors described as an "all-star team" of thieves and killers who cultivated a reputation for brutality to maintain their criminal empire.
In a brief statement just before the sentence was pronounced, Chester apologized for what he called "my behavior" and appealed to U.S. District Judge John Tharp to "Please have mercy on me."
Minutes later, Tharp said Chester, who grew up in poverty coping with a deformity that badly bowed his legs, had squandered his clear intelligence and entrepreneurial mind. "He made a choice to use those talents to advance the cause of evil," the judge said.
Chester was the first of the Hobos to be sentenced since jurors convicted six in January of a racketeering conspiracy that involved at least six slayings, including the 2013 shooting of a star government witness, Keith Daniels, in front of his two small stepchildren as they screamed a few feet away.
Prosecutors had asked for a life sentence. Assistant U.S. Attorney Patrick Otlewski told the judge that Chester was "unrepentant and a disease to society."
Defense attorney Beau Brindley had requested a 20-year term, portraying his client as primarily a drug dealer. "That does not a life sentence make," he added.
Tharp said he seriously considered a life sentence, but concluded Chester had marginally less blame for the killings because he never actually pulled a trigger. At the same time, Tharp said Chester knew what the other gang members were up to, had "embraced the murder and mayhem" and profited from it.
Chester's lavish spending included $645,000 at a casino in Hammond, Indiana, according to prosecutors. His lieutenants once stole a $200,000 gold chain from then-NBA player Bobby Simmons at gun-point outside a nightclub.
A government filing says Chester displayed his brazenness by attending court during his recent conspiracy trial with a balloon stuffed with drugs in his system a day after a jail visitor handed him the contraband. It cited an intercepted email to a girlfriend in which Chester said he had just $2 left to his name and intended to sell the drugs to inmates to pay his lawyer, whom he praised.
"Jesus is there with me every day and so is Beau Brindley," he wrote.
Testifying at his trial, Chester denied the existence of the Hobos street gang, despite his full-arm tattoo emblazoned with the words: "Hobo: The Earth is Our Turf."
The judge also sentenced Hobos gang member Stanley Vaughn to 20 years in prison for a racketeering charge, to be served consecutively to a sentence he is currently serving on a drug conspiracy charge.
Judge sentences Stanley Vaughn to 20 years for racketeering, to run consecutive to current federal prison term. Brings total years to abt 42— Patrick Smith (@pksmid) August 10, 2017
Hobos hit man Paris Poe is scheduled to be sentenced Friday. He killed Daniels days after Chester's arrest and after Daniels testified to a grand jury in the conspiracy case. Poe shot Daniels more than a dozen times at close range as the man's 4-year-old stepdaughter and 6-year-old stepson looked on.
WBEZ's Patrick Smith contributed reporting to this story.