Gangster Disciples boss Sammy Armstead convinces judge to cut his drug sentence

Judge Rebecca Pallmeyer told the Chicago gang leader to prove he deserved to get out early. More than a year later, she agreed he had and cut his 30-year term by five years.

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U.S. District Judge Rebecca Pallmeyer.

U.S. District Judge Rebecca Pallmeyer worried about Sammy Armstead’s long criminal record. So she told him to prove he deserved to have his prison sentence cut. More than a year later, she decided he’d done that.

Sun-Times file

Former Gangster Disciples boss Sammy Armstead has won a hefty reduction in his drug-conspiracy prison term after a federal judge made an unusual deal with him.

In 2019, Armstead asked U.S. District Judge Rebecca Pallmeyer to cut his sentence. Prosecutors had said he controlled sales of heroin and crack cocaine in a 10-story Chicago Housing Authority building at 340 S. Western Ave., where the gang hauled in as much as $10,000 a day.

But he was a changed man, he told the judge.

His lawyer knew she might not buy that, given Armstead’s long criminal record. So he suggested she give Armstead time to prove he was worthy.

“The court accepts that invitation,” Pallmeyer wrote on June 19, 2019, inviting the lawyer to bring back Armstead’s request after a year.

He did. Attorney Daniel Hesler told the judge that Armstead spent the last year “trying to be boring, and he is succeeding. Society has nothing to fear from the man he now is.”

On Dec. 21, the judge made her decision. She noted that Armstead is the only one of the 29 people convicted in the case that dates to 2002 who’s still in prison and cited his contrition and his accomplishments: working for years in prison, where he rose from a sewing-machine operator to a “floor coordinator,” also earning a GED and training for a commercial driver’s license.

But she also pointed to his “very troubling criminal history,” which includes convictions for armed robbery and a shooting.

So Pallmeyer decided she couldn’t let the 53-year-old Armstead walk out of prison immediately. Instead, she reduced his sentence by five years. That means he’ll get out in early 2023 rather than in 2028.

Prosecutors opposed cutting his sentence, saying it wouldn’t “promote respect for the law.” U.S. Attorney John Lausch was one of the prosecutors on the case, which originally resulted in a life sentence for Armstead in 2004. In 2016, that was reduced to 30 years.

Armstead’s latest break was a result of the 2018 federal First Step Act, which gives those convicted of selling crack cocaine a chance to challenge their sentences based on the lower penalties Congress enacted about a decade ago. Dozens of people convicted in Chicago’s federal courts have gone free based on First Step challenges.

In 2001, the year before the arrest for which he’s now in prison, Armstead was elevated to the rank of governor of the Gangster Disciples street gang, according to prosecutors. They said that put him in control of the gang’s illegal drug business on the West Side and had an informant who secretly recorded the meeting in which he was elected to the position.

“Get the right product out there. Pump up the building. Someone can make enough so everybody eats for the rest of the month,” Armstead was recorded saying.

Jimmy Hansen, the police chief in Akeley, Minnesota, knows about Armstead’s past and still wants Armstead to visit his small town, he said in a letter to Pallmeyer last summer. He heard about Armstead from Ronald Smith, a former Gangster Disciples member who’s now a pastor in Minnesota. Hansen said Smith visits schools to discourage gang membership and that Armstead could do the same.

“I need him as a tool to stop kids from going astray,” the Minnesota police chief wrote.

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