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Judge delays sentencing for Hobos member groggy from meds

Gregory "Bowlegs" Chester, the head of a murderous “super gang” that terrorized Chicago’s South and West sides for 10 years, was sentenced by a federal judge Thursday morning. | File photo

The near-certain prospect of spending the rest of his life in federal prison was weighing on Byron “B-Rupt” Brown on Tuesday, so he doubled down on his anti-anxiety medication before his trip to the downtown federal courthouse.

But it turned out the extra meds only prolonged Brown’s anxiety. Brown was still slurring and slightly unsteady on his feet as he stood in front of U.S. District Judge James Tharp Jr. six hours after taking the medication, so the judge postponed the sentencing a week despite protests from Brown and his attorney, Gregory Mitchell.

“This is going to be perhaps the most significant day in Mr. Brown’s life,” Tharp said. “I want to understand that he knows what is going on.”

Brown told the judge he took the medication because he was worried about keeping his cool in the courtroom.

“I didn’t want to be overactive,” he said. “I wanted to be as presentable as possible to calm myself. I have these outburst, these tantrums, sometimes.”

In the end, Brown stayed calm.

“I’m focused enough to go on,” Brown said softly, and in vain, to the judge, just before a marshal placed his hand on his shoulder and led him out of the courtroom.

It probably did not help that Brown has claimed to have misunderstood instructions he received in Tharp’s courtroom on the day he signed his plea deal.

In 2014, Brown was one of the first Hobos members to cut a deal with prosecutors, agreeing to a deal that spared him from a potential death sentence in exchange for his cooperation against other gang members. In 2015, he tried to withdraw his guilty plea and said he’d lied to the grand jury and did not want to take the witness stand at trial.

Tharp wouldn’t let Brown out of the deal, pointing out that Brown had been asked repeatedly in court if he was coerced or threatened into taking the plea deal at a court hearing in 2014.

Brown’s claim that he lied to the grand jury led to a flurry of motions by his co-defendants and triggered a clause in his deal that will all but certainly land Brown a mandatory life sentence. Had he kept his end of the deal, Brown, 32, would have received a 35- to 45-year federal sentence. Brown already is serving 25 years on murder charges in state court.

Six of Brown’s former co-defendants were convicted in December after a 15-week trial that did not include any appearances from Brown on the witness stand. Prosecutors linked the Hobos to eight murders and multiple shootings and robberies on the gang’s turf on Chicago’s South Side.

In his plea agreement, Brown admitted to being the triggerman in three killings: the 2007 execution of Eddie Moss, a semi-pro basketball player Brown mistook for a rival gang member, and Kenneth Mosby and the Daniel Dupree, whom Brown shot and killed less than a week apart in May 2009. Brown also said he was present at two other Hobo slayings.

Mitchell, who was appointed to represent Brown after Brown split with the lawyers who negotiated his plea agreement, said Brown had hoped to get his sentencing over with.

“He’s a thoughtful person, and he’s been thinking about this case a lot for a long time,” Mitchell said. “He’s not being flippant here. He’s very remorseful.”