The reputed leader of Chicago’s Wicked Town gang faction and one of his top lieutenants pleaded guilty Tuesday to racketeering conspiracy involving a string of murders, shootings and robberies in exchange for reduced sentences.
The plea deals reached with Wicked Town boss Donald Lee, 43, and one of his top “shooters,” Torance Benson, 33, avert a lengthy retrial that was ordered after U.S. District Judge Thomas Durkin found the jury had not been fully informed about promises made to certain cooperators in the case. Jury selection in the retrial had been scheduled to begin Tuesday.
Under terms of the plea agreements, prosecutors will recommend a sentence of 30 to 34 years in prison for Lee, down from a mandatory life, court records show. Benson, meanwhile, will get a recommendation of 20 years, instead of a sentence of up to life behind bars, according to his plea agreement.
Both were originally convicted at trial in 2022 in a case that featured testimony from more than 100 witnesses about a seemingly unrelenting onslaught of violence, from blood-splattered cars and bodies on sidewalks to morgue photos, to the accounts of survivors who told the jury harrowing tales of being in Wicked Town’s crosshairs.
The trial presented a crash course in the entrenched gang lifestyle that drives so much of the city’s seemingly endless violence, from typical disputes over drug turf to the more recent phenomenon where tit-for-tat disses on social media foster a cycle of retaliation and murder.
Attorneys for Lee and Benson had argued the prosecution’s case was built largely on the testimony of other Wicked Town members who cooperated with authorities in order to get a break in their own cases. Some of them are killers and admitted liars, while others have been paid by the government both in money and in promises of reduced sentences, according to the defense.
After their convictions, the defense discovered emails by a now-former assistant U.S. attorney on the prosecution team that allegedly contained promises to cooperating witnesses that hadn’t been turned over to the defense before trial.
In one email shortly before trial in 2022, the prosecutor told lawyers for Wicked Town associate Deshawn Morgan, a key cooperator, that his office would likely recommend a 30-year sentence for Morgan if he testified truthfully against his associates.
At trial, however, the jury heard that Morgan was eligible for a sentence of up to 35 years. Durkin wound up sentencing Morgan to 32 years.
In reversing the racketeering convictions, Durkin said he did not make the decision lightly, given the enormous resources that went into the case and the myriad other evidence pointing toward guilt.
But, the judge said, the “fundamental flaw in the trial’s foundation in the truth can only be remedied with a new trial.”
The Wicked Town case was one of two major gang prosecutions to run into trouble recently for similar reasons — both before Durkin.
Earlier this year, Durkin ordered a new trial for reputed Four Corner Hustlers boss Labar Spann after a surprise disclosure showed a different prosecutor had promised a star witness less time in prison than what was told to the jury in that case.
Spann had been facing mandatory life in prison after being convicted in November 2021 of directing or participating in four murders as well as a number of robberies and extortions over the course of two decades.
His retrial is now set to kick off in November.
In his plea agreement, Lee admitted his role in leading the Wicked Town gang, which terrorized portions of the city’s Austin neighborhood for years. Among the racketeering acts in the plea were six murders and several attempted murders between 2000 and 2017, as well as narcotics trafficking and other gang-related crimes, the agreement stated.
Benson, meanwhile, pleaded guilty to racketeering as well as several specific armed robberies and shootings he carried out on Wicked Town’s behalf, court records show.

