The freedom fight of the founder of the Gangster Disciples, Larry Hoover, faces an important test this week

Twenty-six years ago, the prison door seemed to close forever behind Larry Hoover, and many Chicagoans began to forget him.

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

Hoover helped found the violent street gang Gangster Disciples and led it from state prison while serving time for murder. In 1998, a federal judge told Hoover that he had abused his ability to lead thousands – a “gift” from God. He spared Hoover's life.

But Hoover's legacy lived on.

Now Hoover is scheduled to appear in court in Chicago on Thursday for the first time in decades, albeit via video. The 73-year-old hopes that a new judge will overturn the life sentence imposed on him in 1998. Whatever happens, he will still have to serve the earlier murder sentence. He will not be released – unless that is also overturned. But Thursday's hearing could be decisive.

The late U.S. District Judge Harry Leinenweber once called Hoover “one of the most notorious criminals in the history of Illinois.” Many blame Hoover for the chaos and death on Chicago's streets.

One of his lawyers, Jennifer Bonjean, said Today he is a “frail, old man” languishing in the worst prison in the country. Another, Justin Moore, said Hoover is “no longer the man that people associate with his past.”

“He deserves a punishment that reflects his transformation and his commitment to change, not outdated ideas,” Moore said.

U.S. District Court Records

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

A former prosecutor who put Hoover in prison said there are some crimes that are “so great and so heinous” that they do not deserve mercy. Hoover's crimes, in his view, are punishable.

Hoover, however, has said he has renounced the criminal organization he once led. Grammy-winning Chicago rapper Che “Rhymefest” Smith said Hoover showed him for the first time how “hip-hop is used to exert social and political influence.” And another prominent rapper has dismissed the idea that Hoover could ever lead his monolithic gang again.

“It's not like that anymore,” G Herbo said in a 2016 interview with VladTV. “Nobody can command even twenty damn people. … He doesn't even command thousands of people.”

Larry Hoover's rise and fall

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

Meanwhile, Hoover ordered the execution of William “Pooky” Young, whom Hoover suspected of stealing from Hoover's drug stashes. Another gang member shot Young in the head six times and dumped his body in an alley on February 26, 1973.

Hoover was convicted of murder after a trial in December 1973 and a judge sentenced him to 150 to 200 years in state prison. However, that did not stop Hoover from leading the gang. At their peak in the early 1990s, the Gangster Disciples under Hoover's leadership made about $100 million annually in drug sales, according to prosecutors.

Over time, Hoover formed a political action committee called 21st Century VOTE. Hoover's supporters still claim that it organized thousands of people for several protests in front of City Hall in the 1990s. Hoover is also said to have renamed the Gangster Disciples an organization for “growth and development.” The government says that was just a facade.

Hoover was careful not to discuss business matters during his phone calls in prison, so in 1993 the authorities received permission from a judge to listen in on conversations. To do this, a transmitter was installed in the visitor badges of gang leaders who visited Hoover in person.

Hoover was ultimately charged with 40 felony counts, including participating in a continuing criminal organization. A jury found him guilty on all counts on May 9, 1997. Leinenweber found that Hoover's leadership of the gang, the amount of drugs sold, and the amount of cash taken warranted a mandatory life sentence.

Hoover didn't end up in just any prison, however. Rather, his lawyers say, he spent decades in one of the country's most notorious federal prisons, the so-called Supermax facility in Florence, Colorado. Others who served life sentences there included Ted Kaczynski, the so-called “Unabomber,” Terry Nichols, the accomplice in the Oklahoma City bombing, and Joaquin “El Chapo” Guzman Loera, the boss of the Sinaloa drug cartel.

Hoover's lawyers say he spends 23 hours a day in a concrete cell no bigger than a parking space. But prosecutors say he has been housed in the prison's least restrictive unit since July 2015. A report from the District of Columbia Corrections Information Council said the area, known as the “Kilo Unit,” is used to house “high-profile” inmates for security reasons.

Attempts to release Hoover from prison on parole failed over the years. In December 2018, Trump signed the First Step Act, a law that, among other things, retroactively implemented certain criminal justice reforms enacted since 1998. Some of Hoover's co-defendants have already received clemency from the courts.

Former federal prosecutor Ron Safer, who led the prosecution of the Gangster Disciples, advocated for reduced sentences for some of these 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 that was almost twice what it is today, “ridiculously high.”

“How many lives have to be taken and how many families destroyed before you get to a crime where you say, 'As horrific as it is, life imprisonment is the right outcome,'” Safer asked.

Safer said he felt “empty” on the day of Hoover's conviction in 1998 — that “justice had been done” but that it was “deeply sad.” He does not plan to attend Thursday's hearing.

“I just don't feel the need to go through it again,” Safer said. “It makes me sad to talk about it.”

A different legacy

Leonard “GLC” Harris, a 46-year-old rapper and entrepreneur from Chicago, sees Hoover's legacy differently. Harris collaborates with Ye, formerly Kanye West, in music and is trying to win Hoover's freedom. Harris said he believes Hoover had a positive influence on young people.

He counts himself among them, having joined Hoover’s “Growth and Development” organization at a young age.

“In Mr. Hoover's organization, I learned the five Ps of life: good preparation prevents poor performance,” Harris said. “And I have applied that in my everyday life from elementary school to today.”

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

Those supporting Hoover's release also point to his initiatives, which included food and school supply drives. Some point to his connection with Save the Children Promotions, which raised money for the community by hosting hip-hop concerts.

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

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

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

The book questioned whether the Hamburg Club was really made up of a “tough, street-fighting mob of thugs” involved in the Chicago race riots of 1919. And it notes that Daley was elected president in 1924.

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

“The mayor is afraid of me,” Hoover said in the song, which also referenced his Ghetto Prisoner clothing line. “I'm telling these young boys to put down their guns and get the ballot.”

“We consider Mr. Hoover a political prisoner,” said Harris, the rapper known as “GLC.” “We do not consider him a crime boss. His greatest crime he ever committed was to show that he had the ability to organize.”

Harris denies that Hoover has any connection to current criminal activity. So does another man who will be watching closely what happens in Blakey's courtroom: Hoover's son.

Larry Hoover Jr. has been in touch with his father on and off over the years, but he said he has never been able to visit him more than four times a year. When he does, they reminisce. His father wonders “why nobody can fix the youth. Where is the world going? Why is it so bad out here?”

He said the criminal justice system blamed his father for things beyond his control.

“They want to leave him a legacy like Al Capone, although I think his legacy would be more like that of Malcolm X,” Hoover Jr. said. “That's why I'm going to continue to work to make sure his legacy remains positive, no matter what. He was definitely more than just a gangster. He was a real leader and tried to lead people in the right direction.”

He said he was “cautiously optimistic” about Thursday's hearing, but his family had been in a similar situation before.

“I can't get excited about these things anymore,” said Hoover Jr., “because we've been there so many times and the reaction was always the same.”