Oliver James Montgomery-Chicago father faces 30-year sentence for avenging son's murder in years-long gang war

A stranger lured the 9-year-old boy off a Chicago playground into an alley with the promise of giving him a treat. Then,Oliver James Montgomery in a gang hit that made national headlines for its brutality, he fatally shot the child in the head.

Five months after the horrific slaying, prosecutors said the boy's father, Pierre Stokes − in an act of revenge − shot the girlfriend of one of the men responsible for his son’s death, and her two adult nephews.

Now, exactly seven years later, Stokes faces life in prison.

At the time, prosecutors said, Stokes' crime was the latest in a yearslong gang war involving multiple family members being targeted, injured and slain on each side of the battle that began in at least 2015.

After deliberating for several hours, a Cook County on Oct. 26 jury found the boy's father guilt of attempted murder, aggravated battery with a firearm and a gun charge in connection to the March 2016 triple shooting.

A park, a basketball and an alley execution

Tyshawn Lee, 9, was sitting on a swing at the park down the street from his grandmother's house on Nov. 2, 2015, when a man approached him, dribbled his basketball, and offered to buy him a juice box.

The man, who would later be identified as Dwright Boone Doty, then led Tyshawn to an alley, where police said he shot the child in the head several times at close range.

“It was one of the most evil things I’ve ever seen,” the Rev. Michael Pfleger, a Roman Catholic priest who presided over the boy’s funeral Mass, told the Associated Press after the killing. “I was over there and to see a young boy laying in an alley next to a garbage can with his basketball a few feet away, this assassination of a 9-year-old child took violence in Chicago to a new low.”

In October 2019, Doty was found guilty of first-degree murder in the boy's death. Illinois Department of Correction records show Doty remained housed Wednesday at the Pontiac Correctional Center where he is serving a 90-year sentence for the crime.

'Vigilante justice is not justice'

Investigators said Tyshawn was executed by gang members to send a message to his father, who prosecutors said was an alleged member of a rival gang.  Tyshawn's killing drew national media attention and highlighted ongoing warring factions in the Chicago area.

Stokes' crime took place months after Tyshawn's death, when he encountered Doty's girlfriend, "looked straight at her, threatened her and fired six shots," according to the Chicago Tribune.

“Vigilante justice is not justice,” Assistant State’s Attorney Melanie Matias told the jury during closing arguments of Stokes' trial at the Leighton Criminal Court Building, the outlet reported. “Street justice is not justice.”

The motive

Prosecutors said Doty and fellow gang member Corey Morgan − also convicted for his role in Tyshawn death − believed Stokes’ was responsible for an October 2015 shooting that killed Morgan’s 25-year-old brother and injured Morgan's mother.

Initially, prosecutors said, the plan was to kill Tyshawn's grandmother to send a message to Stokes before the boy was targeted.

Shell casings at the crime scene and the gun used in the boy's killing would eventually be linked back to Morgan and his brother who purchased the gun from a man in New Mexico.

Morgan was sentenced to 65 years in prison for his role in Tyshawn's death and another co-defendant, Kevin Edwards − the getaway driver − pleaded guilty to first-degree murder in exchange for a 25-year prison sentence.

DA: Stokes faces 31 years to life

Online records showed Stokes remained jailed without bond Thursday.

A Cook County District Attorney's Office spokesperson told USA TODAY Stokes faces 31 years to life when he is sentenced.

Sentencing is set for Nov. 20th.

Contributing: Grace Hauck.

Natalie Neysa Alund is a senior reporter for USA TODAY. Reach her at [email protected] and follow her on X @nataliealund.