Without the stabilizing influence of his wife, Rolling began a series of armed robberies. In the summer of 1979 he was jailed for robbing a convenience store. Paroled in 1984, he returned to Shreveport but soon began traveling. In July 1985 he robbed a shop in Clinton, Mississippi, and was sentenced to 15 years but served just three. On 6 November 1989 Rolling committed his first killings, slaughtering three members of the Grimmson family. Tom and his 8 year old grandson Sean had been stabbed repeatedly. Tom's 24 year old daughter Julie, a petite brunette ,was slashed and mutilated, her corpse covered in bite marks and then washed and posed sexually on her bed
On 17 may 1990 Rolling shoot his father in the head and stomach in an argument over whether the car window should be open or shut. His father survived the assault but Rolling fled to Gainesville, Florida, thinking he would be arrested. On 24 August Rolling murdered Sonja Larsen, 18, and Christina Powell, 17, in their home. One of the girls was sodomized and the other had hir nipples cut off. On 27 August Rolling murdered 18 year old Christina Hoyt and then cut off her head and put it on a nearby bookshelf. Her naked corpse was washed and posed as Jolie Grimmson had been. The next day Tracy Paules and manual Taboada both 23, were found dead in their apartment. Tracy had been sodomized and both had been stabbed several times. Rolling continued his burglary spree until he was arrest on 1 September. A DNA swab linked him to the Gainesville killings.
In the autumn of 1991 Rolling was sentenced to three life terms plus 170 years in prison for the Tampa burglaries. On 15 February 1994 he pleaded guilty to all charges. On April 20 1994, Rolling was sentenced to die. After a last meal of lobster tail, butterfly shrimp, baked potato and strawberry cheesecake, washed down with tea, Rolling was excited at 6.13 pm on 25 October 2006.