Wicked Town boss gets 34 years in prison after plea deal calls off second trial

A man who led a street gang labeled the “most vicious” ever prosecuted in Chicago’s federal courthouse, and who once faced mandatory life in prison, has instead been sentenced to 34 years behind bars.

It’s the result of a deal the feds struck after U.S. District Judge Thomas Durkin ruled this summer that Wicked Town street gang boss Donald Lee deserved a new trial because a prosecutor made undisclosed promises to witnesses ahead of Lee’s first trial in 2022.

Rather than go to trial a second time, Lee pleaded guilty in September to a racketeering conspiracy and admitted his role in six murders. He also gave up many appeal rights.

When it finally came time to sentence Lee on Thursday, Durkin called him a “really dangerous person” who would have spent the rest of his life in prison had it not been “for a mistake by the government.” The judge said Lee should not be released one day early.

Durkin even went so far as to call a pardon “laughable — but no longer unimaginable — in today’s world.” He told Lee “if anyone is thinking in any way of shortening your sentence,” they should “take a look at the crime scene photos.”

The judge made that comment one day after Gangster Disciples co-founder Larry Hoover sought clemency from Gov. JB Pritzker, following a commutation by President Donald Trump.

Durkin’s sentence means Lee, who is 43, will likely remain in prison until he is nearly 67. Lisa Wood, Lee’s defense attorney, sought a lesser sentence of 30 years.

“He is not a monster,” Wood told the judge. “He is a human being.”

An assault rifle authorities seized from a member of the Wicked Town street gang.

An assault rifle authorities seized from a member of the Wicked Town street gang. | U.S. District Court

U.S. District Court

The terms of Lee’s deal required a sentence between 30 and 34 years behind bars. Durkin also had the option of rejecting that deal. But prosecutors pointed to “the deterioration of evidence,” the controversy over the undisclosed promises, and concern that witnesses might refuse to testify a second time around. It all elevated the risk of Lee’s acquittal in a new trial.

The feds say the “core mission” of Lee’s West Side gang “was gaining respect through murdering rival gang members.” They say Lee earned his place in the gang with his own killing spree.

Within a month of joining the gang in July 2000, prosecutors say Lee “began his ascent to leadership” by murdering Lamont Ware. The feds say Ware “became the collateral damage of a fight over $10 bags of heroin.”

In December 2002, they say he took part in the murder of Ernest Moore, who was shot amid a dispute over drug sales in Sweet Clover Park.

Finally, the feds say Lee “secured his position as Wicked Town chief” by murdering John Johnson, the leader of a faction of the Four Corner Hustlers. The killing occurred amid an attempt to broker peace between the two gangs, prosecutors say.

Lee also admitted his role in the murders of Charlie Weathers, Malcolm Willie and Kishaun Mobley.

“Lee ruled with an iron fist and fostered a culture of killing,” the feds wrote in a recent court memo. “He rose through the ranks by murdering three people in a span of three years and then bred younger members to become killers like him, all in the name of Wicked Town.”

Lee and Wicked Town “shooter” Torance Benson were convicted at trial in 2022. But Durkin ordered a new trial in June over what he determined were undisclosed promises made to witnesses in the case by then-Assistant U.S. Attorney John Mitchell.

Mitchell, who is now in private practice, has denied making undisclosed promises. His former colleagues also disagreed with the judge’s characterization.

In a May 2022 email, Mitchell allegedly relayed his expectation that, “if the sentencing were tomorrow,” prosecutors would recommend a 30-year prison sentence for Deshawn Morgan, a Wicked Town associate who pleaded guilty and testified against Lee and Benson.

Mitchell also wrote that, “we reserve the right to reconsider.”

Morgan was sentenced in August 2024 to 32 years in prison.

Prosecutors disclosed Mitchell’s email to Lee and Benson’s attorneys after sentencing preparations were underway for their clients earlier in 2024, records show. The defense lawyers say “the flood gates opened” after that disclosure, and they learned that Mitchell made similar comments to others who testified against the men.

Benson also pleaded guilty in September to a racketeering conspiracy, and Durkin sentenced him last week to 20 years in prison.

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