Gregory "Bowlegs" Chester, Hobos Gang Leader, Gets 40 years in prison

As the reputed boss of the Hobos super gang, Gregory "Bowlegs" Chester ran a narcotics empire that peddled massive quantities of cocaine, crack and heroin, federal prosecutors said. But it was in his darkest hours, in the moments when Chester's life was threatened by another gang's gunfire or by federal authorities closing in that prosecutors say Chester showed the true measure of his power.

After Chester was shot outside his girlfriend's apartment building, the Hobos went after the rival Black Disciples street gang they believed responsible, according to prosecutors. In September 2007, a team of Hobos tracked down the gang's leader, Antonio "Beans" Bluitt, as he left a funeral home, killing him and a passenger in a car with so many shots that Chicago police ran out of placards to mark the spent shells. A cigar was found still hanging from Bluitt's mouth.

In April 2013, after the feds arrested Chester on heroin distribution charges, Hobos lieutenant Paris Poe cut off an electronic monitoring device and gunned down informant Keith Daniels outside the Dolton apartment where he had been moved by authorities for his safety, according to prosecutors. Dressed in all black and wearing a mask, Poe shot Daniels more than a dozen times in front of his fiancee and two young children, authorities said.

On Thursday, Chester, who was convicted with five other reputed Hobos leaders of racketeering conspiracy charges alleging the gang carried out eight murders over a decade, was sentenced to 40 years in prison.

Chester, 40, made a brief statement to the judge, saying, "I want to apologize to the court and my family for my behavior and ask that you please have mercy on me. That's it."

Prosecutors had sought life in prison, calling Chester "unrepentant and a disease to society." But Chester's lawyer, Beau Brindley, argued that while evidence linked his client to the Hobos "enterprise," he wasn't a killer and didn't deserve a life sentence.

In handing down his sentence, U.S. District Judge John Tharp described Chester as the "most influential" Hobo and said he shared culpability in the murders, but the judge drew a distinction between Chester and the triggermen.

Tharp called it a "tragedy" that Chester didn't use his skills, energy, ambition and entrepreneurial spirit to help others better their lives. "He made the choice to use those talents to advance the cause of evil," the judge said.

Later Thursday, Tharp sentenced Stanley "Smiley" Vaughn, another reputed Hobos leader, to 20 years in prison, the maximum possible, for his involvement in two slayings and five attempted murders. Vaughn, 39, was ordered to serve the sentence on top of a nearly 22-year prison term he is already serving for a separate conviction for conspiring to distribute heroin downstate.

"If that is the functional equivalent of a life sentence, he's earned it," the judge said.

Three other reputed Hobos gang leaders — Poe, Arnold Council and Gabriel Bush, who were convicted with Chester and Vaughn — are scheduled to be sentenced.

Following a marathon 15-week trial that ended in January, the jury found that Poe, Council, Bush and Vaughn carried out five murders, some by themselves or with one other. But the jury held those four as well as Chester and William Ford responsible for all eight murders by its guilty verdict on the racketeering conspiracy count.

Prosecutors alleged that the Hobos represented a new breed of gang that was made up of members from various gangs who once were rivals. Many of the Hobos started in the now-demolished Robert Taylor and Ida B. Wells public housing complexes from factions of the Gangster Disciples and the Black Disciples street gangs, according to prosecutors.

Formed after the larger gangs in Chicago began to fracture, prosecutors said, the Hobos were "an elite killing team" that transcended traditional gang rivalries and welcomed people from rival gangs "so long as they demonstrated the necessary willingness for violence and crime."

The Hobos ruled by fear, terrorizing the South and West sides from at least 2004 through 2013, robbing drug dealers of narcotics at gunpoint and instilling fear through violence, including 16 shootings in addition to the eight murders, according to prosecutors.

Using high-powered weapons, the Hobos opened fire on one victim outside a day care, another at a crowded block party. The Hobos went after informants, too, killing one outside a barbershop.

The gang's killings were calculated, well-planned and meant to send a message that its members were "a force to be reckoned with and that they would go to the most extreme lengths for power and money," prosecutors said in a court filing this week.

Not since El Rukn trials two decades ago had so much violence been alleged against a single gang.

Some witnesses at the trial appeared intimidated by the gang's reputation for violence. Several testified only after warnings they would be held in contempt of court. But Mack Mason, a former auto body shop employee, refused to take the stand, saying some of his family still lived in the area that the Hobos operated in. The judge ordered him jailed for 60 days.

Testifying in October, former NBA player Bobby Simmons said he couldn't remember details of the night he claimed he was robbed at gunpoint of a necklace worth more than $100,000 outside the Ice Bar in River North in 2006. It was only after Simmons was confronted with his own grand jury testimony that the Chicago native and former DePaul University star acknowledged Poe had snatched the diamond-studded necklace from his neck, then fired at least 14 shots at his truck as Simmons gave chase across the South Side.

The centerpiece of the case was the alleged murders of two informants who were cooperating with law enforcement against the gang. Jurors heard evidence that Poe and Council fatally shot Wilbert "Big Shorty" Moore outside a South Side barbershop in 2006 because they believed Moore had provided information to police that led to a raid on a Hobos residence.

After prosecutors rested their case in early December, the trial took a dramatic twist when Chester made the unusual decision to testify in his own defense. In three days on the witness stand, Chester admitted to dealing drugs but denied he was the leader of the Hobos and even went as far as to suggest that the gang did not exist.

Chester, who walks with a severe limp due to a childhood bone disease, denied taking part in any shootings or killings and scoffed at the notion that anyone with a disability could be the head of such an allegedly violent enterprise.

He also sought to distance himself from Daniels' killing, saying he had no motive to order the hit even though Daniels' cooperation had led to Chester's arrest on drug charges days earlier. Chester told the jury his mother was good friends with Daniels' mother and that she had already lost another son to violence.

"Keith Daniels is like family to me," Chester testified. "His mother is like my mother. I mean, I felt her pain. I know what she went through, and I wouldn't ever want to see her go through anything like that again."

During a tense cross-examination by prosecutors, Chester's memory grew hazy on many points. The cross-examination nearly derailed when prosecutors asked Chester about an elaborate arm tattoo depicting a pair of eyes — and what appear to be horns — overlooking the now-razed Robert Taylor Homes along with the word "Hobo" and the phrase "The Earth is Our Turf."

Chester testified that the tattoo was a tribute to a slain friend nicknamed Hobo and that the eyes represented God looking down over the public housing projects where they were raised.

Some of the trial's most dramatic testimony came from Daniels' fiancee, Shanice Peatry, who testified she saw a gunman walk up to their car and open fire though the front windshield while she sat with Daniels and their son and daughter, then ages 4 and 6.

Peatry said she instinctively ducked into the back seat to push the kids to the floor while Daniels bailed out of the passenger side and fell to the ground. The gunman took his time, she said, walking over to Daniels and standing over him, pumping round after round into his chest as their children screamed.

"It was so many (shots) I couldn't count," said Peatry, pausing at times in her testimony to shake her head and draw a breath. "It kind of felt like it was in slow motion to me, like he wasn't in no rush."

Before he jumped into a waiting SUV, the assailant walked close enough to Peatry for her to see dreadlocks sticking out from under his mask and peer into his eyes. She knew instantly it was Poe, she said.

Two weeks later, the jury watched a heartbreaking video interview of Daniels' son talking about what he'd witnessed that day. Seated at a low table with colored markers in front of him, the boy fidgeted and kicked his feet as the interviewer coaxed details out of him.

"I was covering my ears because those gunshots was too loud," the boy said. "My sister said, 'Don't get out, Daddy! Don't!' ... My daddy got out and that's when he got shot in the leg. ... He tripped over a rock. He was on the ground and he got shot again."

Thanks to Gregory Pratt.

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