Hobos gang leader sentenced to 40 years in prison

Gregory “Bowlegs” Chester “embraced the murder and mayhem” wreaked over a decade by the Hobos street gang.

He “contributed to the carnage,” U.S. District Judge John J. Tharp said. And he cannot wash his hands of the blood spilled amid the gang’s reign of terror in Chicago.

Still, the judge stopped short Thursday of branding Chester the undisputed leader of a so-called “super gang” the feds have made him out to be. And while a jury tied him to two murders, Tharp said the evidence showing Chester actively ordered the killings fell short.

That’s why, in the end, Tharp sentenced Chester to 40 years in prison at the end of a two-hour hearing, acknowledging the convicted gang member is a man of many talents who chose “to use those talents to advance the cause of evil.”

In doing so, Tharp gave a nod to the sentencing of the murderous Paris “Poleroski” Poe, set for Friday. The fellow Hobos’ victims included an FBI informant gunned down in front of his girlfriend and two children. The judge said the evidence against Chester did not rise to the same level as that against Poe, who maintains his innocence.

Chester, 40, hugged defense attorney Beau Brindley after his sentencing. Chester, who once survived being shot 19 times, got his nickname from a bone disease that makes it difficult for him to walk. But he stood before Tharp on Thursday, dressed in orange jail garb.

“Your honor, I want to apologize to the court and to my family for my behavior and ask that you please have mercy on me,” Chester said. “That’s it.”

Tharp called Chester “a leader” of the Hobos. But Assistant U.S. Attorney Patrick Otlewski called him “the leader” of the gang — and “unrepentant and a disease to society.”

Later Thursday, Tharp gave Stanley “Smiley” Vaughn, an admitted member of the Hobos who pleaded guilty rather than go to trial, 20 years in prison. The judge said he must serve that sentence in addition to a 22-year prison sentence Vaughn is already serving.

The Hobos largely grew up in the Robert Taylor Homes, and Otlewski said Chester took advantage of the housing project’s demolition — and how it disrupted other gangs — to form the tight-knit group the feds labeled “an all-star team of the worst of the worst” of Chicago street gangs.

Chester, Poe and four other Hobo leaders spent months on trial last year. A jury heard evidence of eight murders, 16 shootings and eight robberies between 2004 and 2013. In the end, the jury convicted Chester and the rest of a racketeering conspiracy.

The feds say Chester committed perjury during the trial by lying on the witness stand. They also said he smuggled drugs into the downtown Metropolitan Correctional Center by swallowing a balloon filled with narcotics during a visit with a girlfriend. They said he sold drugs in the MCC to make money to pay Brindley after the trial.

In reaching their verdict, jurors connected Chester to the murders of FBI informant Keith Daniels and New Town Black Disciple leader Antonio “Beans” Bluitt. Brindley argued there was not enough evidence to tie Chester to the killings, and the judge agreed.

The feds say a caravan of Hobos assassinated Bluitt after a funeral in September 2007. They say gang members sprayed 41 bullets into his car — so many that Chicago police ran out of placards to mark spent cartridge casings found at the scene.

Bluitt died with a cigar still hanging from his mouth, gunned down three months after Chester was shot outside his girlfriend’s apartment in a neighborhood associated with Bluitt’s gang.

But most notorious among the Hobos’ killings was the death of Daniels, who turned on the gang and wore a wire while buying drugs from Chester.

Days after Chester’s arrest in 2013, the feds say Poe cut off an electronic monitoring ankle bracelet and hunted Daniels down in Dolton, where the FBI had helped him move.

Poe stepped from behind a shrub and opened fire on the car carrying Daniels, his girlfriend and their two “gorgeous little kids” home from a Sunday family dinner.

Daniels leaped from the car. A bullet pierced his heart. And as he gasped for breath on the ground in front of his 6-year-old boy and 4-year-old girl, Poe fired “gunshot after gunshot after gunshot” into his body, the feds say.