Chicago man faces up to 120 years in prison for Joliet Denny’s murder, robbery

A Will County judge will decide the sentence of a Chicago man who faces up to 120 years in prison for his role in the 2019 robbery and murder of a man outside of a Joliet Denny’s restaurant.

Prosecutors had been willing to negotiate a plea deal with Joshua Anderson, 25, that would have resulted in a lesser penalty.

Anderson’s two accomplices had already pleaded guilty to their involvement in the crime. One of them was going to testify against him.

But Anderson rejected the offer from prosecutors on the eve of his four-day trial, which began on Dec. 10.

Anderson even attempted to refuse to wear any civilian clothes during his trial. He told his mother at one pretrial hearing, “They’re going to find me guilty, anyways.”

It took the jury only 23 minutes on Dec. 13 to find Anderson guilty of the 2019 first-degree murder and robbery of Gregory Brown, 36, of Crest Hill, according to the Will County State’s Attorney’s Office.

On Feb. 21, Anderson is scheduled to return to the courtroom of Will County Judge Amy Bertani-Tomczak. She will decide the prison sentence of Anderson, who faces between 56 to 120 years behind bars.

Anderson’s former girlfriend, Bobbie Ollom, 29, of Seneca, was sentenced to 18 years in prison after she pleaded guilty to armed robbery of Brown.

Anderson’s cousin, Christopher Parker, 28, of Chicago, was sentenced to 37 years in prison after he pleaded guilty to Brown’s murder.

In Ollom’s testimony, she provided extensive details on the plot to rob Brown. Her testimony was supplemented with surveillance videos, photos and text messages.

Ollom said Anderson and Parker were pushing her to set someone up for a robbery and Brown was chosen as the “target.”

She testified part of the plan was for her to lure Brown by promising him sex in exchange for $850.

Ollom said that on that day she picked up Anderson and Parker in Chicago in her vehicle and the trio made their way to Joliet for the robbery.

But instead of meeting Brown at his house, Ollom said she had to go meet him at Denny’s because he wanted to eat there.

Ollom testified at one point she persuaded Brown to go to her vehicle in the Denny’s parking lot.

When Brown entered Ollom’s vehicle, she said she heard Parker say, “Give me the money,” and then heard a gunshot.

She said at the time, Parker “had the gun.” Ollom testified she saw Parker pull Brown’s body out of the vehicle, drop him on the ground and rifle through his pockets.

After the shooting, Ollom said she drove to Interstate 55 to head for Chicago. Ollom described Anderson’s demeanor as “normal” and she heard laughter coming from him and Parker.

“For me, I was very scared and shocked and I didn’t want to speak,” Ollom testified.

Ollom said Anderson and Parker split the cash they stole from Brown and Anderson gave some of that cash to his mother.