Gangster Disciples founder Larry Hoover's quest for freedom faces key test this week

The prison door seemed to permanently slam shut behind Larry Hoover 26 years ago, and many Chicagoans began to forget about him.

Those who remember still compare him to Al Capone, the leader of a ruthless 1920s criminal syndicate that cemented the city’s bloody, violent reputation. Others say he studied Richard J. Daley, the “boss” mayor of Hoover’s youth — and then paid for his political ambition.

Hoover helped form the violent Gangster Disciples street gang, and he ran it from state prison while serving time for murder. In 1998, a federal judge told Hoover he’d misused his ability to lead thousands — a “gift” from God. He gave Hoover life.

But Hoover’s legacy carried on.

Now, Hoover is set to appear in a Chicago courtroom Thursday for what appears to be the first time in decades, albeit by video. The 73-year-old hopes a new judge will undo the life sentence handed to him in 1998. Whatever happens, he’ll still have the earlier murder sentence to serve. He won’t go free — unless that's eventually undone as well. But Thursday's hearing could be crucial.

The late U.S. District Judge Harry Leinenweber once called Hoover “one of the most notorious criminals in Illinois history.” Many hold Hoover responsible for mayhem and death in Chicago’s streets.

One of his attorneys, Jennifer Bonjean, said he’s now a “frail, elderly man” languishing in the country’s harshest prison. Another, Justin Moore, said Hoover is “no longer the man people associate with his past.”

"He deserves a sentence that reflects his transformation and commitment to change, not outdated perceptions," Moore said.

Any success Hoover enjoys will be through a 2018 law signed by then-President Donald Trump. But the decision to grant mercy now rests with U.S. District Judge John Blakey, nominated to the bench in 2014 by then-President Barack Obama. Hoover's attorneys are asking him to agree to a new sentencing hearing that could lead to leniency.

A former prosecutor who helped put Hoover in prison said there are some crimes “so large and so heinous” that they don’t warrant mercy. He said Hoover’s qualify.

But Hoover has said he’s renounced the criminal organization he once led. Grammy-winning Chicago rapper Che “Rhymefest” Smith said Hoover gave him his first glimpse of “hip-hop being used to leverage social and political impact.” And another prominent rapper has dismissed the idea that Hoover might ever lead his monolithic gang again.

“It’s not like that no more,” G Herbo said in a 2016 VladTV interview. “Nobody can even command 20 f---ing people. … He’s not commanding no thousands of people.”

Larry Hoover’s rise and fall

Hoover and David Barksdale created the Gangster Disciples by merging two street gangs in the late 1960s. They ruled as “King Larry” and “King David” until Barksdale was killed in 1974.

Meanwhile, Hoover ordered the execution of William “Pooky” Young, who Hoover suspected of stealing from Hoover’s drug stash houses. Another gang member shot Young in the head six times and dumped his body in an alley on Feb. 26, 1973.

Hoover was convicted of the murder after a trial in December 1973, and a judge sentenced him to 150 to 200 years in state prison. That didn’t stop Hoover from running the gang, though. At its height in the early 1990s, prosecutors say the Gangster Disciples brought in about $100 million a year in drug sales under Hoover’s leadership.

Along the way, Hoover formed a political action committee called 21st Century V.O.T.E. It’s still cited by Hoover’s supporters for having organized thousands of people to participate in multiple City Hall protests in the 1990s. Hoover also purportedly rebranded the Gangster Disciples as a “Growth and Development” organization. The feds say it was a facade.

Hoover was careful not to talk business during his jailhouse phone calls. So in 1993, authorities got a judge’s permission to monitor conversations by placing transmitters in visitor badges given to gang leaders who would go see Hoover in person.

Eventually, Hoover was charged with 40 crimes, including engaging in a continuing criminal enterprise, and a jury found him guilty of all charges on May 9, 1997. Leinenweber found that Hoover was subject to a mandatory life sentence because of his leadership of the gang, the amount of drugs sold and the amount of cash grossed.

Hoover didn’t wind up in just any prison, though. Rather, his attorneys say he’s spent decades inside one of the country’s most notorious federal prisons, the so-called supermax facility in Florence, Colorado. Others who have served life sentences there include Ted Kaczynski, the so-called “Unabomber”; Terry Nichols, the Oklahoma City bombing accomplice; and Joaquin “El Chapo” Guzman Loera, the Sinaloa drug cartel kingpin.

Hoover’s attorneys say he spends 23 hours a day in a concrete cell no larger than a parking space. But prosecutors say he’s been housed in the prison’s least restrictive unit since July 2015. A report by the District of Columbia Corrections Information Council says that area, known as the “Kilo Unit,” is used to house “high profile” inmates out of concern for their safety.

Efforts to win Hoover parole from his state sentence have failed over the years. Then, in December 2018, Trump signed the federal First Step Act. Among other things, it made certain sentencing reforms enacted since 1998 retroactive. Some of Hoover’s co-defendants have already seen mercy under the law.

Former federal prosecutor Ron Safer, who led the Gangster Disciples prosecution, supported sentencing breaks for some of those defendants. But not for Hoover.

Safer said Hoover “was the undisputed leader of a gang that terrorized the city” and was responsible for a murder rate nearly double today’s “ridiculously high” level.

“How many lives need be taken, how many families ruined, before you get to a crime where you say, ‘You know, as horrible as it is, life in prison is the right result’?” Safer said.

Safer said he felt “empty” the day of Hoover’s sentencing in 1998 — that “justice was served” but it was “profoundly sad.” He said he doesn’t plan to attend Thursday’s hearing.

“I just don’t have the desire to revisit that,” Safer said. “It makes me sad talking about it.”

A Different Legacy

Leonard “GLC” Harris, a 46-year-old Chicago rapper and entrepreneur, sees Hoover’s legacy differently. Harris has partnered with Ye, formerly Kanye West, on music and in efforts to win Hoover’s freedom. Harris believes Hoover had a positive impact on young people.

He counts himself among them, having joined Hoover’s “Growth and Development” organization when he was young.

“Being in Mr. Hoover's organization taught me the five p’s on life: proper preparation prevents poor performance,” Harris said. “And I applied that to my everyday life from elementary school up until now.”

Hoover brought structure to people’s lives, he said.

Those in support of Hoover’s release also point to his initiatives that included food and school-supply drives. Some reference his affiliation with Save the Children Promotions, which raised money for the community by hosting hip-hop concerts.

Wallace “Gator” Bradley, a former Gangster Disciples enforcer, said the judge should give Hoover a break “in the name of redemption, fairness and humanity.” And he said Gov. JB Pritzker should commute Hoover’s state-court sentence.

“They know that he is no longer a threat,” said Bradley, 72, of the North Side.

Hoover reportedly said he was inspired by Daley’s rise from the Hamburg Athletic Club to the world of politics. Former Sun-Times columnist Mike Royko’s 1971 book on Daley, titled “Boss,” was of interest to Hoover, according to people who knew him.

The book questioned whether the Hamburg club was really made up of a “tough, street-fighting mob of brawlers” who participated in Chicago’s 1919 race riot. And it notes that Daley was elected to be its president by 1924.

Hoover spoke about his own political ambitions on “A Visit with Larry Hoover,” a track on Houston hip-hop group Geto Boys’ 1996 album, “The Resurrection.”

“The mayor’s scared of me,” Hoover said on the track, which also referenced his clothing line, Ghetto Prisoner. “I'm telling these young boys to put them guns down and pick up that ballot.”

“We view Mr. Hoover as a political prisoner,” Harris, the rapper known as "GLC," said. “We don't look at him as a gang boss. His biggest crime that he ever committed was to show that he had the ability to organize.”

Harris rejects Hoover’s connection to current criminal activity. So does another man who will be watching to see what happens in Blakey’s courtroom: Hoover’s son.

Larry Hoover Jr.’s access to his father has varied over the years, but he said he has never been able to visit more than four times annually. When he does, he said they reminisce. He said his father wonders “why nobody can get the youth in order, like ‘What is the world coming to? Why is it so bad out here?’”

He said the criminal justice system has held his father responsible for things he didn’t control.

“They want to give him a legacy of Al Capone, when I think his legacy was going to be like a Malcolm X,” Larry Hoover Jr. said. “So, I'm going to keep pushing for his legacy to be a positive one, regardless of what happens. There definitely was more to it than just him being a gangster. He was a real leader and he was trying to lead people in the right direction.”

He said he’s “cautiously optimistic” about Thursday’s hearing. But the family has been in this situation before.

“I can't get excited about these types of things anymore,” Larry Hoover Jr. said, “because we've been there so many times before and the response has been the same.”