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Hobos 'Super Gang' Leader Up For Sentencing; Feds Want Life

CHICAGO (CBS) -- The head of a murderous "super gang" that terrorized Chicago's South and West sides for 10 years is set to be sentenced by a federal judge Thursday morning.

Prosecutors want U.S. District Judge John J. Tharp to give Gregory "Bowlegs" Chester, 40, life in prison. They say he led the Hobos, known as "an all-star team of the worst of the worst" of Chicago's street gangs. Evidence at a marathon trial of its leaders last year tied it to eight murders, 16 shootings and eight robberies between 2004 and 2013.

However, Chester's defense attorney maintains he was simply a run-of-the-mill drug dealer who ran with bad and "perhaps even evil people."

The feds say Chester used the Hobos' criminal enterprise to fund a lavish lifestyle. He allegedly bought luxury cars, took trips abroad and cashed $645,283 at the Horseshoe Hammond Casino. Prosecutors also say he paid for a lawyer when his fellow Hobos got into legal trouble and bought them gifts when they walked out of prison.

Chester once survived being shot 19 times, and prosecutors say he carried MAC-11 and FN 5.7 handguns to social events as innocuous as a picnic. He got his nickname from a bone disease that makes it difficult to walk. And during the monthslong trial that ended early last January, Chester's attorney told the jury, "there are no crippled kingpins."

The feds countered in a court memo this week that "there is and his name is Gregory Chester."

"Chester built his leadership and power in the Hobos through skillful manipulation of others, and by peddling money, drugs, handguns, and a 'gangster' lifestyle to young men on the South Side," Assistant U.S. Attorney Patrick Otlewski wrote.

The Hobos' deadly reputation appeared to be on display during the monthslong trial when former NBA player Bobby Simmons took the stand and claimed not to remember much about the night senior Hobos Paris "Poleroski" Poe and Arnold "Armstrong" Council robbed him of a $200,000 white gold necklace. A federal inmate, Mack Mason, simply refused to testify out of concern for his family's welfare. It cost Mason an extra two months behind bars.

A jury ultimately found Chester, Poe, Council and three other men guilty of a racketeering conspiracy and five murders. The jury tied Chester to the murder of FBI informant Keith Daniels — gunned down by Poe in front of his girlfriend and two young children — and New Town Black Disciple leader Antonio "Beans" Bluitt — assassinated after a funeral on a Sunday afternoon with a cigar still hanging from his mouth.

The feds say a caravan of Hobos sprayed 41 bullets into Bluitt's car when they killed him, so many that Chicago police ran out of placards to mark the spent cartridge casings they found at the scene.

The Hobos allegedly killed Bluitt three months after Chester was shot outside his girlfriend's apartment in a neighborhood associated with Bluitt's gang. Meanwhile, Poe killed Daniels shortly after Chester's arrest by federal authorities on heroin distribution charges. They said Poe cut off an electronic monitoring ankle bracelet and tracked Daniels down in Dolton, where Daniels had moved with help from the FBI after he flipped on Chester.

Otlewski called Daniels' murder "the true pinnacle of Chester's influence and power."

Beau Brindley, Chester's defense attorney, said the feds lacked any true evidence to connect Chester to the murders. Even if the Hobos dedicated "each pull of the trigger to his exalted leadership," that does not make Chester responsible, Brindley wrote in a court memo this week.

"Without evidence that Mr. Chester ever communicated a desire for those shootings to occur [of which there is none], he is no more culpable for them than Jodie Foster is culpable for the attempted assassination of Ronald Reagan," Brindley wrote.

Prosecutors say Chester's criminal conduct continued behind bars. They said he committed perjury when he took the stand during last year's trial. They also say he smuggled drugs into the downtown Metropolitan Correctional Center, swallowing a balloon filled with narcotics last October during a visit from his girlfriend.

Otlewski noted that Chester "had the gall to come to court carrying the balloon of drugs in his system — literally bringing narcotics into the courtroom with him."

In an email, Chester told a different girlfriend he was selling drugs in the MCC to pay his lawyer, according to the feds.

"I have less that [sic] 2$ on my books," Chester allegedly wrote. "But Jesus is there with me everyday and so is Beau Brindley."

(Source: Sun-Times Media Wire © Chicago Sun-Times 2017. All Rights Reserved. This material may not be published, broadcast, rewritten, or redistributed.)

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