'Gainesville Ripper' Danny Rolling Made Friends With Informants, Dated A Writer While Incarcerated

In the northern Florida town of Gainesville in 1990, five young university students were murdered in their own homes over just three days in horrific ways — stabbed in the back, raped, beheaded. The killer was a Louisiana drifter who would come to be known as the Gainesville Ripper. 

Danny Rolling, at 36 years of age, was on the lam, having attempted to kill his retired police lieutenant father by shooting him in the face just months before he went on a crime spree spanning armed robbery to first-degree murder.

Rolling was given three consecutive life sentences in prison for an armed robbery in nearby Ocala that happened right after he had slain the students, and he was already behind bars when he was identified as the suspect in the Gainesville killings. While Rolling was in prison and the prosecution built their case for his 1994 trial, he became close with another inmate: Robert “Bobby” Lewis. 

Rolling and Lewis forged a close relationship, and Lewis became a sort of confidante for the troubled Rolling who blamed childhood abuse for his violent behavior.

Lewis was seeking a reduction of his own life sentence for killing a man in Jacksonville, which explained his cooperation with authorities, according to the United Press International.

Rolling told his friend how he killed the five students — Sonja Larson, 18, Christy Powell, 17, Christa Hoyt, 18, Tracey Paules, 23, and Manny Tobaoda, 23 — both orally and in writing.

According to court documents, the task force who had met with Lewis on occasion refused his attempts to receive incentives in exchange for information.

The friendship between the two murderers was interrupted by a six-month stint in a mental health facility in Chattahoochee, according to the same court documents, but when Rolling returned to Florida State Prison in December 1992, Lewis continued to seek information. Rolling then decided he wanted to help Lewis out so that Lewis could strike some sort of deal.

Lewis was a bit of a character on his own: he was the only person to escape from death row in Florida in a 1978 prison break. His role in uncovering details of the Gainesville murders rendered him the focus of press accounts. His 2001 obituary described him as a “positive, philosophical” man who became “adept in the art of manipulation [with] his own twist” and was proud that  “his involvement in events following the Gainesville student murders spared the student families a prolonged trial.

Rolling had requested, according to court documents of his 1996 appeal, not to be separated from Lewis because he “needed Bobby’s support.” He said he wanted to “see Bobby a free man.. it would break his heart if they could not do anything for Bobby.”

Rolling reportedly told the task force that “Bobby was a worthy soul, and he deserves his chance to make his life good, and out of all of this I’m trying to do something for someone.” The task force rejected Rolling’s request, as they had done to Lewis, to which Rolling referred to his father: “I was raised by a policeman. I know what you gentleman can do when you put your mind to it.”

Rolling said that he agreed to talk to the task force because someone had trashed his cell, destroying a Valentine’s Day card he had worked on for more than five hours. While Rolling initially met with the task force alone, he asked for Lewis to join them; he wanted his friend to make statements and answer questions in his lieu.

Lewis would be his “confessor.” His “mouthpiece.”

Rolling refused to answer any questions on his own; he would simply confirm or deny what was said. His friend Bobby Lewis relayed sordid details of the murders where Rolling cut the nipples off of two of his victims and beheaded one.

Lewis told the task force that the reason for the murders was that “Rolling was subjected to inhuman conditions while incarcerated at Parchman Penitentiary in Mississippi.” Rolling himself blamed that time period in prison in a 17-page letter he sent to the Associated Press in 2000, alleging that a “mangy dog gets more consideration” and that living in filth “drives you crazy as a loon.”

Lewis said in a separate interview that Rolling was like a “werewolf” who would watch his victims at home for hours or days on end. Lewis also told authorities that Rolling wanted to cooperate with the FBI to study serial killers, reported the Orlando Sentinel.

Lewis’ information spread beyond the five murders for which Rolling received death sentences: Rolling told him that he had killed a family of three in Shreveport after stalking the young woman of the family. While Rolling was never formally charged with the 1989 murder of the Grissom family, the police considered him the only suspect in light of this testimony, blood sample evidence, and similarities with the murders of the young university students, reported the Gainesville Sun.

“Lucifer told me eight souls for every year I’d done in prison,” said Danny Rolling according to CNN.

Lewis testified that he had had hundreds of hours of conversations with Rolling about the murders, and along with another inmate, helped him fake a suicide attempt so that they could stay in the same wing of the prison.

According to court documents, Lewis even bragged that Rolling, who he called a “woman and kid killer” wanted him around for security since even the guards would leave him alone if Lewis asked. He reportedly exchanged many letters with freelance journalist Sondra London about Rolling. On his alleged use of Rolling, Lewis wrote: "It not something I'm proud of -- it just survival -- in a animal world."

Rolling appealed the death sentences and tried to get the confessions suppressed, alleging that Lewis had acted as a de facto state agent and tried to profit from their friendship.

While in prison, Rolling would also receive comfort from an unexpected source: Sondra London, the journalist, who achieved a degree of fame from writing a book on her ex-boyfriend, suspected serial killer G.J Schaefer. Sondra started a correspondence with Rolling, leading to a book and also an engagement. They were engaged for a period, and seemingly, very much in love.

London described meeting Rolling as something she wasn’t prepared for, according to the Washington Post: “Standing before my hungry eyes was one gorgeous hunk of man.” Rolling, to the Post, described his relationship with London as “deep as the Amazon river… and just as wild!”

London and Rolling’s book “The Making of a Serial Killer: The Real Story of the Gainesville Murders,” led to them being sued under the Son of Sam law, which prevents convicted felons from profiting from their stories. In 1998, a judge ruled that proceeds from the book to the tune of $20,000 could be seized from London for work published in relation to the Gainesville Ripper story, reported the New York Times.

Rolling was executed in 2006 after singing a hymn and eating a lavish dinner, and never quite achieved his dream of being a “superstar” like Ted Bundy — though he undoubtedly still harbored these dreams in prison.

“Mark of a Killer” explores the methods and the madness of infamous serial killers, starting with the premiere on January 20, on Oxygen, Sundays 7/6c.

[Photo: Gainesville Police Department]