On four out of five IQ tests, including one he took at age seven, Chester scored 70 or lower,[2] the lowest of which was 57 on a Vineland Adaptive Behavior Survey, taken in October 1987, when he was 18 years old.

[3] As an adult, he worked on-and-off as a general laborer[4] and was briefly employed as a service worker at a Luby's cafeteria.

On April 8, after his trial was set for August that same year, Chester paid bail, during which time he graduated high school.

Chester was released on parole on February 13, 1990, and detained by police just over a month later on March 16 for theft, possession of a criminal instrument, and evading arrest.

On April 1, Chester was arrested for burglary and two counts of aggravated assault, which never went to trial after the district attorney dismissed the case.

[4][6] Five months after his parole release, between August 1997 and February 1998, Chester perpetrated at least 25 burglaries, five sexual assaults, and ten shootings in Port Arthur, Texas.

[1][6] During most home invasions, Chester disabled the telephone landlines, unscrew outdoor security lights, and wore either a hockey mask or home-made balaclava to conceal his identity.

The same evening, Chester used the gun to fire several shots through the open bedroom window of a nearby house, injuring Peggy Johnson and Debra Ferguson as they slept, also fatally striking a pet dog.

Chester knew DeLeon, as they were formerly co-workers at Luby's, and had been stalking the victim for an indeterminate amount of time with intentions of robbing her.

During the rape, 38-year-old Willie "Billy" Ryman III, the maternal uncle of the DeLeon sisters, arrived outside the home by car, accompanied by his fiancée Marcia Sharp.

At the request of Claire, Chester ran outside to check if there were more people besides Ryman, at which point the sisters locked the door, then went to retrieve a handgun kept for self-protection from upstairs.

He unsuccessfully attempted to shoot open the lock and upon spotting Sharp inside, Chester fired two gunshots at her, but missed.

Chester tried to find another way back inside the house, but was scared off by a stray shot fired by his former hostages and fled down the street.

[5][15][16] On February 8, thirty hours after the rape of the DeLeon sisters and the murder of Willie Ryman, Chester was arrested for an unrelated violation of city ordinance.

The DNA samples matched with those found at the DeLeon crime scene further connected Chester to three additional rapes.

Chester entered a guilty plea and during the trial, he made multiple outbursts, threatened the lives of police officers, prison guards, court officials, and the families of jurors, and at one point declared, "If I hadn't shot my brother-in-law, I'd still be out there shooting white folks.

It took the jury only 11+1⁄2 minutes to agree on a death sentence for Chester after he went on a tirade during which he threatened to kill employees of the district attorney's office if he ever got released and have "his homies" kill a police officer who had arrested him on burglary charges in 1988, as well as two detectives involved in the investigation of his murders should he receive capital punishment.

[6] Since Chester was capable of hiding facts and lying to protect his own interests, using masks and gloves, removing the serial numbers from the stolen firearms, and cutting exterior telephone lines before entering homes to burglarize, he showed persuasively that he was capable of forethought, planning, and complex execution of purpose.

Jefferson County assistant district attorney Wayln Thompson described Chester as "only learning disabled" and "one of the most dangerous individuals we have ever prosecuted".

[14][16] In 2007 and 2008, Chester filed a habeas corpus writ, alleging that his death sentence was against the Eighth Amendment and constituted cruel and unusual punishment.

[3] Out of thirteen federal and state judges, eleven rejected his appeals in their entirety, while the remaining two found only "some merits" in the argumentation.