Faceoff Between Federal Prosecutor, Alleged Hobo Begins

CHICAGO (CBS) -- One month into the federal racketeering trial of the Hobos "super gang," there was a delay in testimony because Gregory "Bowlegs" Chester needed to see a doctor — to check his body for contraband.

What happened Oct. 18 in the Metropolitan Correctional Center came back to haunt Chester on Thursday, when the alleged gang leader gave a federal prosecutor the chance to cross-examine him by taking the stand in his own defense.

"Mr. Chester, explain to the members of the jury how you smuggled synthetic marijuana into the MCC," Assistant U.S. Attorney Patrick Otlewski said, kicking things off.

After some quibbling over the question, Chester admitted he swallowed a balloon filled with K2 synthetic marijuana that was given to him in a potato chip bag by a female friend visiting him at the federal jail. Chester admitted he did so in the middle of the racketeering trial, which could land him in prison for the rest of his life. Getting caught apparently didn't stop him from taking the stand.

"I popped one into my mouth before the guard looked at me," Chester told the jury, adding later that he "had that one balloon down for about an hour."

"It was worth a lot to me because I need it for my nerve damage," Chester explained.

Otlewski quickly moved on to other alleged deceptions by Chester, setting out at the start of his interrogation to undermine any credibility Chester had established with the jury. Roughly 15 minutes into the questioning, Otlewski earned three warnings from U.S. District Judge John J. Tharp Jr. to refrain from "editorial comments."

Otlewski also earned a rebuke from Tharp for asking Chester "does the god that you worship have horns?"

The rare faceoff drew a nearly full-house in Tharp's 14th floor courtroom. Chester, 39, surprised trial watchers Wednesday by taking the stand in his own defense, setting up a confrontation with the team of federal prosecutors and agents who have been putting Chester and five other alleged Hobo leaders on trial for 13 weeks.

The feds have called the Hobo gang an "all-star team of the worst of the worst" of Chicago's street gangs, and they've tied the gang to nine murders and several other crimes. Authorities have also described Chester as "the undisputed leader of the Hobos." But Chester testified Wednesday that the gang didn't exist, and that the word "Hobo" was the nickname of a deceased friend.

The man with a bone disease that "causes my legs to go bow" has also admitted he was affiliated with the Gangster Disciples and sold heroin at $80 a gram, no less than 50 grams at a time. He said he has been shot twice. On one of those occasions, he was hit 19 times.

His testimony comes as lawyers race to wrap up the significant street-gang trial before Christmas.

Chester said Thursday that he was at Ice Bar the day alleged Hobo enforcer Paris "Poleroski" Poe robbed professional basketball player Bobby Simmons at gunpoint in June 2006. Chester said he saw Poe and alleged Hobo Arnold Council at the bar that night, but none of the men were there together.

Poe allegedly robbed Simmons of a $200,000 white gold and diamond necklace outside the bar. That kicked off a high-speed car chase as Simmons, then a member of the Milwaukee Bucks, followed Poe and Council through the streets of Chicago. Poe and Council shot at Simmons at least 15 times, Simmons has testified.

Later, when Otlewski asked Chester whether he considered himself a big-time drug dealer between 2004 and 2013, Chester told the prosecutor, "I consider myself a bona fide hustler," explaining that he also gambled at casinos and planned concerts.

"I hustled," Chester said. "That's what I do. I'm a hustler."

Chester's cross-examination began in the middle of Thursday afternoon and will likely continue on Monday.

(Source: Sun-Times Media Wire © Chicago Sun-Times 2016. All Rights Reserved. This material may not be published, broadcast, rewritten, or redistributed.)

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