Convicted Hobo gang member turns to ex-FBI agent to administer lie-detector test

According to the FBI, Gregory “Bowlegs” Chester was the leader of a hyper-violent Chicago street gang — the Hobos — whose members are suspected of killing a police informant and others to protect Chester.

But in an unusual move, Chester, who is awaiting sentencing on a drug conspiracy conviction last year in federal court, has enlisted a retired FBI agent in his defense.

On April 21, Jay E. Cherry, a former FBI polygraph examiner, gave Chester a lie-detector test that Chester now wants to admit in court as evidence that he’s not a gang boss.

Cherry asked Chester two questions: “On Oct. 22, 2008, did you admit to investigators that you sold drugs?” and “Did you admit to investigators on Oct. 22, 2008, that you were a gang leader?”

Chester, hooked up to a polygraph, answered “no” to both questions.

In an affidavit, Cherry said he recorded “no significant response,” meaning that Chester passed the lie-detector test.

Now, Chester wants U.S. District Judge Gary Feinerman to consider his polygraph exam to counter the government’s efforts to give him an enhanced 20-year sentence for being a gang leader.

Prosecutors say he deserves the hefty sentence because “he was the leader of the Hobos, a violent and dangerous crew of robbers, drug dealers and murderers from at least 2003 to 2013.”

To protect Chester, the Hobos committed at least four murders — including a rival shot to death outside a funeral home in 2007 and a police informant shot in front of his girlfriend and young children in 2013, federal prosecutors say.

The gang also robbed NBA players, according to police sources.

In his court filing, Chester says the Chicago Police illegally arrested him in 2008 and then interviewed him.

He says the police, who were working with the FBI on the case, filed a false report that said Chester admitted to being “the most influential member of the Hobos because he was the most successful drug dealer and breadwinner.” The lie-detector test refuted that, he says.

Chester’s sentencing is scheduled for May 26.