CHICAGO — Infamous Gangster Disciples founder Larry Hoover is set to appear in court for the first time in decades Thursday as his long-shot bid to win freedom comes to a head at Chicago’s federal courthouse.

Hoover, 73, had initially been scheduled to appear in person at the Dirksen U.S. Courthouse, but U.S. District Judge John Robert Blakey later said he would be linked via videoconference, citing “logistical and safety concerns.”

The 1 p.m. hearing is a crucial step in Hoover’s yearslong quest to win early release from his federal sentence under the First Step law passed in 2018, which has already led to reduced sentences for several of his co-defendants.

Federal prosecutors have vehemently opposed such a break for Hoover, arguing he has continued to hold sway over the gang’s hierarchy from the federal “Supermax” prison in Florence, Colorado, even secretly communicating with an underling through coded messages hidden in a dictionary.

Hoover’s attorneys, meanwhile, have claimed that decades behind bars have left him a changed man and that prosecutors have unfairly painted him as a puppet master to try to keep him locked up.

The motion was pending for years before U.S. District Judge Harry Leinenweber, who passed away in June, and has since been transferred to Blakey.

Hoover was already serving a 200-year state sentence for the murder of a rival when he was indicted in federal court in 1995 on charges he continued to oversee the murderous drug gang’s reign of terror from prison.

Hoover was convicted on 40 criminal counts in 1997, and Leinenweber sentenced him to the mandatory term of life.

“I don’t always agree with the guidelines,” Leinenweber told Hoover during that hearing. “Sometimes I think they are too draconian. But in this case, I agree with them 100%.”

For years, Hoover been housed in solitary confinement at the Supermax prison, which counts a number of high-profile and notorious detainees, including Sinaloa cartel boss Joaquín “El Chapo” Guzmán, Sept. 11 terrorist attack plotter Zacarias Moussaoui, and Jeff Fort, the Chicago gang leader who founded the El Rukns.

Hoover’s attorney, Jennifer Bonjean, argued in a motion in 2022 that there was “no evidence whatsoever” that Hoover had received any communication from other Gangster Disciples while in federal prison, and said the government’s efforts to paint him as an unrepentant criminal are baseless.

“It is not in dispute that many people from all walks of life, including politicians, celebrities, community activities and people who self-identify as GDs, support Hoover,” Bonjean wrote. “Indeed, the fact that Mr. Hoover is supported by individuals who are not gang members is what frightens the government the most. The government does not want to see a rehabilitated Hoover. It wants to hold on to its narrative of Hoover as the most notorious dangerous, and violent man on the planet.”

Prosecutors, however, have contended that granting Hoover a sentence reduction “would send a shockwave through the community and embolden gang members who still look to Hoover as their inspirational leader.”

In a 2022 memo asking Leinenweber to deny the request, Assistant U.S. Attorney Julia Schwartz called his life sentence “richly deserved.”

“Hoover’s crimes are among the most serious ever prosecuted in this district, such that reducing his life sentence would undermine the statutory goals of promoting respect for the law and deterring others from engaging in gang violence and large-scale drug trafficking,” Schwartz wrote.

Even if Blakey were to grant Hoover’s release request, he would not walk free. But he would likely be transferred out of the federal prison system to continue fighting his state conviction from a jail cell much closer to his home.

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