Admitted gang killer tells federal jury he’s seeking ‘justice’ by testifying against associates

Dante Dockett is by his own admission a ruthless killer.

A longtime member of Chicago’s Wicked Town gang faction, Dockett pleaded guilty in federal court to fatally shooting six people and trying to kill two others over a four-month span beginning in 2016, a trail of bloodshed stretching from the streets of Chicago’s West Side to a quiet home in Kankakee.

But even a gang loyalist like Dockett has a tipping point. He told a federal jury last week that after learning in 2018 that members of his own gang had executed his longtime friend over suspicions he was a snitch, he decided to do the unthinkable — wire up for federal agents and help them solve the crime.

“He was like a little brother to me,” Dockett, 44, testified of his friend’s slaying Wednesday. “I wanted justice.”

Dockett’s unlikely turn as a federal cooperator took center stage in the racketeering trial of two of his longtime associates in the Wicked Town gang, Donald Lee and Torance Benson, who are accused of participating in a criminal enterprise responsible for a string of murders, attempted murders, robberies, assaults and drug trafficking stretching back more than 20 years.

Among the incidents charged in the indictment was the brutal January 2018 slayings of Dockett’s friend, Donald Holmes Jr., and Holmes’ girlfriend, Diane Taylor, who were shot in the back of the head execution-style while sitting in a car on West Arthington Street.

After wiring up for investigators in Cook County Jail, Dockett captured two Wicked Town associates, Darius Murphy and Demonte Brown, allegedly talking about their roles in the slayings, leading to murder-for-hire charges filed against them in 2019.

Of all the cooperators who have testified in the trial so far, Dockett has the most baggage. Even before he took the witness stand Wednesday, prosecutors referred to Dockett in open court as “a serial murderer and a sociopath.”

The comment came during an argument to bar evidence that in addition to killing multiple human beings, Dockett also abused and tortured dogs as part of a dogfighting operation.

“I know it sounds crazy, but people who hear about dogfighting are going to have a really hard time” Assistant U.S. Attorney John Mitchell said outside the presence of the jury. U.S. District Judge Thomas Durkin agreed, allowing only limited testimony that Dockett had faced animal cruelty charges in Cook County that were later dropped.

Still, attorneys for Lee and Benson had plenty of ammunition. In an often heated cross-examination that stretched for hours, they mocked his purportedly altruistic motives for testifying, noting that he went from facing a possible death sentence or life in prison to a plea deal where prosecutors have agreed to seek only 20 to 30 years behind bars.

“You killed six people in four months?” attorney Steven Shobat, who represents Lee, asked Dockett at one point. “So if you get 20 years, that works out to about three years and four months (in prison) per murder?”

Dockett, dressed in orange jail clothes and with a slightly graying goatee, blinked back at Shobat through large, round eyeglasses. “Correct,” he said without expression.

Like several other cooperators who have testified in the trial, Dockett’s gang history goes back to his early teens, when he was “blessed in” to Wicked Town, a notoriously violent faction of the Traveling Vice Lords headquartered in the 500 block of North Leamington Avenue.

Dockett testified that he was in and out of prison beginning in 1996, when he was 18, for convictions ranging from possession of a firearm and robbery to narcotics trafficking. In 2005, he was arrested for shooting and wounding a rival gang member and was eventually sentenced to 12 years in custody for aggravated battery with a firearm.

Dockett testified that the gang scene was vastly different after his 10-year stint in prison. The oaths they’d taken as young members of the Traveling Vice Lords to love and protect one another seemed to be meaningless to the younger members of the gang, he said.

“I seen no more unity when I came home,” Dockett said. “Everyone was out for himself.”

By that time, Dockett was considered a “five star,” an older member of a gang who didn’t necessarily need to follow anyone else’s orders, according to courtroom testimony. It was that status that led to him taking matters into his own hands.

On Aug. 16, 2016, Dockett shot a rival gang member in the wrist as part of an ongoing dispute over drug turf, he said.

The next month, another drug dispute led to a confrontation with a Four Corner Hustler nicknamed “Ruthless.” After driving into rival territory with Lee with the intent to discuss the issue, Dockett said he saw Ruthless approaching their car with what appeared to be the butt of a gun sticking out of his pocket. Dockett said his “body language” was threatening, prompting him to open fire.

Jurors watched surveillance video of the incident showing three muzzle flashes before Ruthless falls to the ground, shot twice in the chest. He was taken to a hospital in critical condition, but survived.

Just two days after that shooting, Dockett testified that he was contracted by another gang member, Donald Holmes Sr., the father of his good friend, to travel to Kankakee and find a drug supplier who Holmes believed had robbed him of narcotics and cash during a home invasion several years earlier.

Dockett picked up two associates and made the 60-mile drive to the home of the victim, Reginald Neal. Dockett said they knocked on the door, and after Neal’s son let them in, they immediately pulled guns and accused Neal of robbing the gang.

When Neal, 56, protested, one of Dockett’s associates shot him in the head, Dockett testified. Dockett then went to Neal’s son, Dangelo, 24, and shot him in the head as he was lying on the floor. When Neal’s other son, Davante,, 21, heard the commotion and opened the door to his bedroom, Dockett shot him in the head too.

Dockett testified that he killed the sons because he “thought they would be witnesses.” On the way out of the home, they grabbed money off a table and Dockett fired one more bullet into the father’s lifeless body, he testified.

Dockett said he did it so that each of his associates would know they were culpable in Neal’s shooting “and no one would tell on each other.”

The Kankakee slayings were followed two months later by a double-murder back in Wicked Town’s territory, Dockett testified. Two days before Christmas 2016, he confronted rival drug dealer Derrick Jones, who was suspected of stealing from the gang, on the street in the 500 block of North Laramie Avenue.

According to Dockett’s testimony, he shot Jones’ cousin, Stephen Tucker, 20, in the head before chasing Jones, 21, into a basement stairwell and firing several shots, fatally striking him in the body.

The final murder in Dockett’s string of violence occurred in February 2017. He told the jury he had been working with an associate of the Black P. Stones to distribute narcotics when a fight broke out between the associate and Antoine Watkins. During a chase, Dockett opened fire on Watkins with a .45-caliber pistol, striking him fatally.

Watkins’ body was found hours later by police in a vacant lot in the 600 block of North Long Avenue, according to a Tribune report.

Dockett’s two violent years of freedom ended in September 2017 when he was arrested by Chicago police on weapons and drug charges as well as a misdemeanor count of mistreatment of animals, records show.

Dockett said he was still in custody on that case when he learned that his friend, Holmes Jr., and Taylor, who was a cousin of Dockett’s girlfriend, had been ambushed and slain. He said when he heard it had happened right outside Murphy’s apartment, he immediately suspected Murphy was involved but kept quiet at first.

Federal investigators first approached Dockett about cooperating in 2018, before his indictment in U.S. District Court. He said he agreed to wear a wire on Murphy and Brown, who were in custody in Cook County Jail on unrelated charges, and try to get them to talk about the slayings of Taylor and Holmes.

In a series of recordings played for the jury last week, Murphy told Dockett that their fellow gang associate, Deshawn Morgan, had contracted the hit on Holmes, who Morgan suspected incorrectly was cooperating with law enforcement.

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In one conversation on Oct. 15, 2018, Murphy told Dockett he “didn’t know (Holmes) from a can of paint. So it ain’t my fault I killed him,” according a transcript provided to the jury.

“I ain’t gonna worry about it,” Holmes said.

Lee was later captured in intercepted jail calls talking with Wicked Town members about his suspicions that Dockett had flipped. “Not you. Not you Dante,” he lamented in one call played in court, saying that even the “toughest (expletives)” seemed to be turning against them.

The gang member on the other end of the line told Lee that once you put on a wire for the government, “You killed yourself.”

“Once you put that (expletive) on, you’re their agent forever,” he said.

jmeisner@chicagotribune.com