Location Madison Correctional Institution
Offenses Attempted Murder, Drug Abuse, Felonious Assault
Sentence Min/Max 18 YEARS/30 YEARS
Date Admitted 05/09/1995
Next Eligibility Hearing Date 03/31/2020
Gary Roberts attempted to murder his ex-wife, Kim Caldwell. Roberts has previously been convicted of murder in Hamilton County Case No. B-7401855.

In 1974, Roberts had been in a confrontation with Dennis Worley regarding some of Worley’s estranged wife’s furniture. Roberts drove to Worley’s home around 1:30 a.m. and honked his horn, which caused Worley to go see what he wanted. Upon reaching the car, Roberts fired two shots from the car at Worley, killing him.

In 1994, Roberts was apparently upset that his Caldwell’s new boyfriend was making his children do things. These were things like eating dinner before getting dessert.

Roberts confronted his ex about this, which led to her telling him that he would get his children over her dead body. Roberts told her that could be arranged and that he was going to “pull an OJ [Simpson] on her.”

A few days later, Roberts drove to where Caldwell was staying. Hearing a car with a loud exhaust system outside the front door, she got up to look outside. That is when Roberts fired three shots at her.

One shot hit her boyfriend, causing a flesh wound. One shot missed. Though he later said that he was intending to hit only the boyfriend, one shot hit Caldwell in the chest.

This was not a spur of the moment decision. Tony Oakes was with Roberts when this happened. He knew what was going to happen. He was upset with Roberts about things because he did not expect Roberts to point the gun over the passenger seat, which led to his having the gun fired inches from his face. Afterwards, they went to a bar and told a few bartenders they knew that they might be in some trouble involving drugs and that if anyone asked, they should say they had been at the bar that evening.

After shooting Caldwell, Roberts went back to the house he and others had been drinking and smoking crack at. At the house were Roberts, Oakes, and Sylvia Smith, who was dating Roberts. When the news ran a story about the police looking for Roberts, he decided that Smith could not be trusted. So he refused to let her leave. When police finally showed up to search the house at least a week later, she was still wearing the same clothes she had on the night the murder occurred. Notably, Roberts told her that if she opened her mouth about what she knew that there would be a “triple OJ.”

Roberts has killed one person and attempted to kill more. He is a threat to society and should not, under any circumstances, be given the chance to kill or try to kill anyone else. He should serve the maximum time allowed by law in prison for his violent crimes.

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