How to Catch A Criminal: Raising the Ripper

Every officer with a decent amount of time on the job knows the unexpected turns an investigation can take. Seeing a major case through to completion often involves giving up on a theory and taking your investigation in a different direction as new information becomes available. In How to Catch A Criminal, we look at the many ways not-so-perfect crimes are solved. This month, a broken man pays it forward.

We are all products of our environment. Your upbringing and the values your parents instilled in you are a major part of the person you are today. That being said, who you are and how you live your life is ultimately in your hands. A difficult childhood or mediocre parenting may be serious setbacks in a person’s development, but they do not justify improper behavior as an adult. Sometimes life isn’t fair, and we simply must play with the hand we’re dealt. There are those few, however, that would rather pass their suffering on to others.

This article appeared in the November/December issue of OFFICER Magazine. Click Here to subscribe to OFFICER Magazine.

In late August 1990 terror struck Gainesville, Florida, when five students were gruesomely murdered in a matter of days. On Aug. 24, 18-year-old Sonja Larson and 17-year-old Christina Powell were both stabbed to death with a large knife after being sexually assaulted inside their apartment near the University of Florida. The killer first attacked Larson in her upstairs bedroom, gagging her so she could not scream for help. Powell then suffered the same fate downstairs after being bound, gagged, raped, and stabbed repeatedly in the back. To add an extra layer of depravity, their bodies were posed in a lewd manner, something that would become the killer’s signature. The following day, 18-year-old Christa Hoyt, a student at the nearby Santa Fe Community College, was attacked as she returned home just before noon. Her attacker was lying in wait after prying the sliding glass door open with a screwdriver. Hoyt was strangled unconscious before being bound and gagged with duct tape. After raping her, the killer stabbed her in the back repeatedly and decapitated her. Christina Hoyt’s body was left in a seated position and her head placed on a nearby shelf.

Word quickly spread around town that a killer was targeting female college students. All three victims had brown hair, brown eyes, and were small in stature, indicating the killer was looking for particular victims. As police worked frantically to uncover leads, they realized the killer was as intelligent as he was depraved. The duct tape used on the victims had been removed to prevent fingerprints from being discovered, leaving only the residue. He used various cleaning products on the victim’s bodies in an attempt to ruin any DNA from his sex crimes. Aside from small markings left behind from the screwdriver, his method of entry was clean and quiet. University students were encouraged to walk in groups, keep their doors locked, and remain vigilant, because “The Gainesville Ripper,” as he came to be known, was still on the loose. Classes were cancelled, and many students left the University of Florida campus altogether.

Despite these precautions, the Ripper was still able to claim an additional two victims. On the evening of Aug. 27, 1990, he pried open the sliding door of the home of Manual Toboada and Tracy Paules. Both were 23-year-old University of Florida students, and Paules was a brown haired, brown eyed, petite woman. The Gainesville Ripper had most likely been scouting her as his next victim, but he may not have known about her former football player roommate. The Ripper attempted to make quick work of Toboada, who was asleep in his bed. Instead, he was met with a prolonged fight. Unfortunately, after multiple stab wounds, Manual Toboada could no longer fight back, and he was killed. The racket caused by the fight woke Tracy Paules who ran to her bedroom and attempted to barricade the door. The Ripper still managed to force his way in, bind her with duct tape, rape her, and stab her several times in the back. Traci’s body was found posed in a lewd manner, just like the other victims.

The investigation to this point turned up a few suspects, however they were later ruled out. Manual Toboada and Tracy Paules were the Ripper’s last victims, but it turns out the Gainesville students were not the first to feel his wrath. As the nature of the Gainesville Ripper’s crimes made headlines, police in Shreveport, LA noticed something peculiar. The Gainesville murders were strikingly similar to an unsolved triple homicide that occurred on November 4, 1989. On that evening, 55-year-old Tom Grissom, his daughter, 24-year-old Julie Grissom, and her nephew, 8-year-old Sean Grissom, we’re all murdered inside their home. The intruder used the same methods as the Gainesville Ripper, including cleaning Julie’s body to remove his DNA, and leaving her body posed in a sexual fashion. Investigators working the case reached out to authorities in Gainesville to inform them they may be looking for the same suspect. Meanwhile, by September 1990, The Ripper’s killing spree was over. Classes resumed, and the students gradually came back.

After months of chasing leads with no results, police in Florida got a tip from a woman from Shreveport. She recalled a strange man she went to church with by the name of Daniel Rolling. She was friendly with him for a time until one day he told her he had a problem. He enjoyed stabbing people. He also expressed to her that he planned to move to Gainesville someday. Police tracked down Rolling at the Marion County jail where he was serving time for an armed robbery that took place in Ocala, Florida, just a few days after the Gainesville murders stopped. In January 1991, Rolling’s DNA was tested against the few samples detectives were able to find at the Gainesville crime scenes. The DNA was a match, and Rolling was charged with the five “Gainesville Ripper” murders.

Daniel Rolling was the son of a Shreveport police officer who was physically abusive from Daniel’s birth in 1954, all the way to May 1990, when Daniel snapped and shot his father twice. His father survived, but Daniel began living in Gainesville under a fake name, sleeping in a tent near the University of Florida while he bounced from job to job. Daniel Rolling had a lengthy criminal history, but it wasn’t until he attacked the Grissom family that he reached the point of no return. After unleashing his rage on the Grissoms and his father, he could no longer hold back his homicidal tendencies and began seeking out vulnerable woman in Gainesville.

Daniel Rolling plead not guilty, and his trial began in November 1994. However, on the first day of the trial, Rolling informed the judge he wanted to address the court before the proceedings began. Rolling then confessed to the murders and changed his plea to guilty on all five counts. During the sentencing phase, psychologists for the defense testified that Rolling’s childhood trauma resulted in a severe personality disorder, and he may have even developed a second personality which was responsible for the murders. Additionally, his mother begged the court for leniency, as she detailed the decades of abuse she and her children suffered at her husband’s hands. Daniel was first beaten as a baby because he wasn’t crawling correctly. Later, his father killed the family dog as Daniel watched. The constant mental and physical abuse continued until Daniel flunked out of the third grade and began using drugs as an escape from his father. Daniel’s mother argued that he only became The Gainesville Ripper because of his father’s abuse. Despite this testimony, Daniel Rolling was sentenced to death by lethal injection. In 2006, once all appeals were exhausted, Rolling provided a written statement to police in which he finally confessed to killing the Grissom family. He was executed on Oct. 25, 2006.