Charles Benjamin and Christopher Simmons

Victim: Shirley Ann Arras Crook, 46

Murderers: Christopher Simmons, 17, & Charles Benjamin, 15 (16-year-old John Tessmer was originally part of the plan but decided against it)

Crime locations: Jefferson County & Castlewood State Park in St. Louis County

Crime date: September 9, 1993

Crimes: Home-invasion, kidnapping, abduction, torture, murder, & thrill-killing

Weapon: Duct tape, purse strap, & electric wire for restraining

Murder method: Drowning

Murder motivation: Thrill & entertainment

Sentence:  Benjamin-life without parole (LWOP); Simmons-death, later reduced to life in prison

Incarceration status: Simmons-Southeast Correctional Center; Benjamin-Eastern Reception Diagnostic Correctional Center



When Simmons was 17, he decided that he “wanted to murder someone.” He joined up with Benjamin, 15, to plan and carry out the vicious thrill-killing. The victim was 46-year-old Shirley Crook. The murderers broke into her home and abducted her, taking her to a state park. At the park, they hogtied her, covered her face with duct tape, and threw her into a river, causing her to drown. Benjamin was sentenced to LWOP while Simmons was sentenced to death. Simmons appealed his death sentence and his case went before the US Supreme Court. The Court ruled that the juvenile death penalty was unconstitutional and his sentence was reduced.


Christopher Simmons, 17, decided he “wanted to murder someone.” He found younger conspirators, Charles Benjamin, 15, and John Tessmerand, 16. He formed a plan to burglarize a house, tie up the victim, and murder them by throwing them off a bridge. He even bragged to his accomplices that they would “get away with it” because they were minors. 

On the night of September 9, 1993, at around 2:00 a.m., Simmons and his accomplices met up. Tessmer left before Simmons and Benjamin set out. Simmons and Benjamin broke into Shirley’s home in Jefferson County, Missouri. They found a back window cracked open at the back of the home, opened it, reached through, unlocked the back door, and entered. As the home invaders made their way through Shirley’s home, Simmonds turned on a hallway light, which awakened Shirley. “Who’s there?” she asked. Simmonds entered Shirley’s bedroom and the two recognized each other–they had previously been involved in an automobile accident together.

Simmonds ordered Shirley out of bed. When she did not obey the burglar’s command, he and Benjamin forced her onto the floor. Simmons and Benjamin used duct tape to tie her hands behind her back and cover her mouth and eyes. He and his accomplice then stole her car and drove her to Castlewood State Park in St. Louis County. There, they found that Shirley had managed to remove some of the duct tape from her face and had freed her hands. They restrained her hands and feet using a belt from Shirley’s bathrobe, Shirley’s purse strap, and electric wire found on a nearby railroad trestle. They covered her head with a towel and walked her to the railroad trestle, which ran above the Meramec River. The killers then tied her hands and feet with the electric wire in a hog-tie fashion, wrapped duct tape around her entire face, and threw her into the river. Shirley drowned. Her body was discovered by fishermen. Simmons went on to brag about the murder.

Benjamin was convicted and sentenced to life in prison without parole. Simmons was convicted and sentenced to death. The case went through a series of appeals. In 2003 the Missouri Supreme Court held that executing juveniles constituted cruel and unusual punishment. The case then went to the Supreme Court of the United States. In the landmark Roper v. Simmons ruling, SCOTUS ruled five to four that the juvenile death penalty was unconstitutional. Simmons was then sentenced to life in prison without parole. He and Benjamin remain in prison this day.

Written by an NOVJM volunteer.