Shortly after he was arrested in 2021 on racketeering conspiracy charges, reputed Wicked Town gang leader Donald Lee was asked by a federal agent about the execution-style slayings of a suspected police informant and his girlfriend a few years earlier.
The victims, Donald "Don Don" Holmes Jr. and Diane Taylor, had been lured to a West Side alley in 2018 and shot in the back of the head at point-blank range, allegedly by two gang associates who believed Holmes had been talking to law enforcement.
Lee was not at the scene that night, but as the leader of Wicked Town, a notoriously violent faction of the Traveling Vice Lords, he'd instituted a strict "no snitch" rule, and made perfectly clear that violating it was punishable by death, according to federal prosecutors.
So, the question the agent asked Lee was simple: Did Holmes and Taylor deserve what they got?
"Yes, you know why? Because Don Don signed up on the dotted line," Lee allegedly replied in the video-recorded interview. "These streets ain't giving pardons. ... He ratted. So yes, sir, I do believe that."
That chilling statement was presented to jurors in opening statements Monday as the racketeering conspiracy trial of Lee and one of his lieutenants, Torance Benson, got underway at the Dirksen U.S. Courthouse.
Prosecutors alleged the gang that Lee and Benson were part of was a criminal enterprise responsible for a "devastating" amount of violence over nearly a 20-year period, including 19 murders as well as dozens of armed robberies and assaults dating back to at least July 2000.
The victims included rival gang members, informants and innocent bystanders alike, Assistant U.S. Attorney Jimmy Arce said in his opening remarks to jurors. In many cases, the violence was carried out in a way that sent a message to others about who controlled the gang's territory on North Leamington Avenue, he said.
"For close to 20 years, Wicked Town terrorized the West Side of Chicago with brazen acts of violence, in cold blood, out in the open and in broad daylight," Arce said.
Attorneys for Lee and Benson, however, said the prosecution's case is built largely on the testimony of other Wicked Town members who are cooperating with authorities in order to get a break in their own cases.
Some of them are serial killers and admitted liars, while others have been paid by the government both in money and in promises of reduced sentences, attorney Lisa Wood, who represents Lee, said in her opening statement.
Wood and defense attorney Steven Shobat, who represents Benson, also said prosecutors have little or no evidence tying their clients to some of the shootings, while others may have been the result of self-defense or mistaken identification.
"This case will not be a sprint, unfortunately, it's going to be a marathon," Shobat said. "The evidence will come in witness by witness, but we will get there."
The Wicked Town case is one of a series of conspiracy indictments brought by federal authorities in recent years that use the racketeering statute to hold Chicago's street gangs accountable for a seemingly endless cycle of violence.
The trial comes as authorities continue to grapple with an alarmingly high number of shootings and homicides in the city, which are down slightly this year but still have given Chicago a national reputation for an out-of-control gun culture.
Lee, 41, and Benson, 31, are each charged with racketeering conspiracy and unlawful use of a weapon by a felon. Lee is also charged with two counts of murder in the aid of racketeering, while Benson faces one count of aggravated assault in furtherance of the conspiracy.
If convicted, they each could face life in prison.
Nearly a dozen other members of the Wicked Town gang have pleaded guilty in the case, and several are expected to testify during the two-month trial.
Security is tight at the courthouse. In advance of the trial, U.S. District Judge Thomas Durkin granted prosecutors' request for jurors to remain anonymous, and phones and other electronics have been banned for the general public from both the trial courtroom and an overflow room where spectators can watch a video feed.
Last week, Durkin also suspended all jail phone privileges for Lee, who was accused by prosecutors of violating orders and attempting to reach out to potential witnesses in the case, court records show.
Recently, authorities intercepted a call Lee made from the Metropolitan Correctional Center using the credentials of another inmate in which he discussed not only the names of witnesses, but the order in which they're expected to be called to testify, records show.
The case against Lee and Benson has echoes of the racketeering trial of Labar "Bro Man" Spann, the reputed leader of another West Side gang, the Four Corner Hustlers, who was convicted in the same courthouse last year.
Spann was convicted of overseeing a similarly violent enterprise that resulted in slayings and robberies that terrorized Chicago neighborhoods. He faces mandatory life in prison when he's sentenced later this year.
Although Chicago's once-massive street gangs are now believed to be fractured and less structured, the Wicked Town members nonetheless aligned themselves through rituals and oaths, commemorative tattoos and coded language, according to federal prosecutors.
The gang regularly promoted its violent enterprise on social media, posting comments, photos and videos to proclaim membership in the gang, taunt rival gang members and boast about murders and other acts of violence, the superseding indictment filed last year alleged.
"This wasn't just a social club, a group of guys," Arce said in his opening statement. "They weren't getting together to watch football."
Arce said the founder of Wicked Town, Marquel Russell, 45, will testify that he abdicated control to Lee a few years later, after Lee shot and killed several people over a short span in the early 2000s, including John Johnson, who led a gang faction one street over from Wicked Town's territory.
"You'll see that Donald Lee literally shot his way to the top," Arce said, pointing at Lee seated at the defense table.
As Arce ticked off the homicides included in the indictment, jurors were shown graphic crime scene photos - bullet-shattered car windshields, car interiors stained with blood and an image from the slaying of Holmes and his girlfriend, the bodies still visible in his gray SUV, parking lights on.
Prosecutors in 2019 charged two alleged Wicked Town associates, Demond Brown and Darius Murphy, 21, with conspiracy to commit murder for hire in the shooting of Holmes and Taylor.
According to prosecutors, another gang member, DeShawn Morgan, hired Brown and Murphy to kill Holmes in late 2017 after growing suspicious that Holmes, a fellow member of the Vice Lords, was cooperating with law enforcement.
Months after the slayings, a senior member of the gang who was facing his own federal charges agreed to cooperate with law enforcement and secretly record conversations with Brown and Murphy in Cook County Jail, prosecutors said.
In the recordings, made in September and October 2018, Murphy allegedly described in detail how he had lured Holmes to a purported drug deal and then insisted on getting into Holmes' car.
"I get in the back seat. ... Pow! Pow!" Murphy was quoted as saying. "His (expletive) tried to bail out, I grabbed her by the back of her wig. I said, 'Where you going?' Pow! Pow!"
Less than five hours after the slayings, Brown texted Morgan a screenshot of the Chicago Tribune's breaking news story on the shooting, according to the complaint, which contained an image of the text.
Morgan, Brown and Murphy have all pleaded guilty and are awaiting sentencing.
Another slaying that will be a focus of the trial is the July 15, 2015, killing of Malcolm Willie during a pickup basketball game in Hubbard Park.
Willie's shooting, which was the subject of a lengthy profile by the Chicago Tribune, came while another alleged Wicked Town member, Victor Turner, was seeking revenge for the slaying of his brother the year before, prosecutors said.
According to the Tribune story, Willie had taken a break from the game and was on the phone with his pregnant girlfriend when someone on a bicycle rode by, pulled out a gun and started shooting. As others in the park scattered, Willie dropped to the ground. His friends tried administering CPR, but Willie died after being placed in an ambulance.
Arce told the jury Monday that Turner fired the fatal shots using a gun Lee had given him - another episode of egregious violence that robbed a community of joy on an otherwise pleasant summer night.
"In an instant, this park was turned upside down," Arce said. "It was transferred into a war zone."