Florida’s Most Notorious Serial Killers

Florida Man is just the tip of the iceberg; these five legendary monsters redefined horror in the state

Florida’s reputation for weirdness and #FloridaMan stories may have gained momentum after the infamous 2000 presidential recount. Since then, we’ve had face-eating bath salt junkies, barefoot python hunters, all manner of political malfeasance and more. Florida is its own epic Carl Hiaasen novel, respun as an apocalyptic horror movie.

But the state has long beckoned as a land’s end for wrongdoers and creeps, and among Florida’s dubious distinctions is that the state has churned out an unenviable assortment of some of the nation’s most notorious serial murders.

TED BUNDY

1980 police mug shot of convicted serial killer Ted Bundy in Starke, Florida. (Florida Correctional/ZUMAPRESS.com)

Theodore Robert Bundy was the archetype of the serial killer, the cunning psychopath whose disarming appearance—he was often called “charming,” “handsome” and “intelligent”—concealed a sadistic compulsion to kill—repeatedly—for sexual gratification.

Though serial killers were nothing new, they became a phenomenon in the 1970s: Gacy, Son of Sam, the Hillside Strangler and, ultimately, Ted Bundy dominated national news cycles, suggesting an emerging, and terrifying, trend. Indeed, the term “serial killer” first appeared in the 1980s, having been coined only after this burgeoning epidemic launched new fields of study devoted specifically to this type of crime.

A key facet of the exploration into serial offenders has been the question of nature vs. nurture, and in Bundy’s case, it would almost seem that he was born evil. At the mere age of 3, Bundy’s idea of fun was to surround his sleeping stepsister with kitchen knives, waiting for her to wake up, delighting in her terror with an arctic grin.

Like many serial killers, Bundy was a chameleon, changing his appearance at will and using a variety of ploys to lure victims, like the polite stranger with a cast on his arm who needed help carrying his books. Once a complicit victim was securely in Bundy’s web (i.e., his ’68 Volkswagen Beetle), she would soon become a missing person.

Bundy got off on inflicting grievous injury upon his victims, whom he raped before—and sometimes after—death. As his appetite grew more insatiable, his m.o. grew more brazen and he became less careful. After appearing on the radar of investigators, he moved from the Pacific Northwest to Utah, where he continued killing and was eventually captured. Remarkably, he escaped from custody not once, but twice; the first time from the second-story window of the courthouse law library during a recess in his 1977 preliminary hearing, and the second time that same year from his jail cell.

Bundy went on the lam and ended up in Tallahassee, Florida. Only a week after his arrival, he broke into the FSU Chi Omega sorority house in the middle of the night and surprised four of the residents in their beds with a savage blitz that left two dead. Bludgeoning, garroting and sexually assaulting the young women left him unsated, and shortly after leaving the house, he broke into a nearby apartment and attacked another FSU student with such brutality that her injuries resulted in lifelong disabilities. The following month, he landed in Jacksonville, where he abducted, raped and murdered 12-year-old Kimberly Leach. Authorities spotted him days later in a stolen vehicle and took him into custody.

Despite representing himself at trial with an almost flamboyant cockiness, Bundy was found guilty and sentenced to death, a sentence that was carried out in Florida’s electric chair on January 24, 1989.

AILEEN WUORNOS

Aileen Wuornos 1991 mugshot in Volusia County, Florida. (Pacific Photos)

An overwhelming percentage of serial murders are men. There are a few random cases of women with a genteel knack for poisoning, but serial murdering “black widows” are a small club indeed.

Aileen Wuornos, then, was an exceedingly rare anomaly. And a study in grey.

The inversion of the typical prostitute killer, Wuornos was a prostitute who killed her clients. And depending on what you believe, she was a would-be target who turned the tables on at least one of her victims.

That victim was her first, Richard Charles Mallory, whom she shot to death in his ’77 Cadillac on November 30, 1989. She would later claim that Mallory sodomized and tortured her, promising that her death was imminent, before she pulled a handgun from her purse, shot him to death and then robbed him. Mallory’s lifelong history of sex offenses, incarceration and diagnosis as a likely sociopath tended to corroborate Wuornos’s testimony, though it was never introduced at trial.

Wuornos would go on to murder six additional men until her arrest in January 1991.

A trailer home in Florida owned by Aileen Wuornos. (Sue Russell/BWP Media)

Abandoned by her biological mother shortly after her birth, Wuornos was primarily raised by her grandfather, as her biological father—a pedophile whom she never met—languished in prison for child rape and hanged himself when Aileen was 12. Her grandfather sexually abused and regularly beat her, and after she gave birth to a child (who was later surrendered for adoption) at 13, she was ostracized by her community and peers. She began living in the woods near her home and having sex for money, which would remain her vocation until her 1991 arrest.

During her highly publicized trials, opportunists materialized around her in the guise of supporters. She was represented pro bono by local attorney Steve Glazer, aka “Dr. Legal” in his TV ads, a doobie-rolling, guitar-strumming troubadour who mounted an incompetent and self-serving representation of Aileen. Simultaneously, Aileen was “adopted” by Arlene Pralle, a born-again she-wolf breeder who believed she saw Aileen’s soul through her eyes in newspaper photos, and who ended up collecting substantial payouts for media interviews. The only person Wuornos loved and felt loved by—her lover and sometime accomplice Tyria Moore—testified against her, while selling story rights to Republic Pictures.

Even the cops were cashing in, as three Marion County sheriff’s deputies had reportedly entered negotiations with Republic. The 1992 TV movie that resulted was one of several films about Aileen Wuornos, including two remarkable Nick Broomfield documentaries, and “Monster,” in which Charlize Theron’s portrayal of Wuornos won her an Oscar.

Wuornos was executed by lethal injection on October 9, 2002.

BOBBY JOE LONG

Robert J. Long stands before Hillsborough County Judge Perry Little in a courtroom inside the county jail. (The Tampa Tribune/ZumaPress.com)

It was around 2 a.m. on November 3, 1984. Lisa McVey, 17, had just worked a double shift at a Tampa Krispy Kreme and was bicycling home when a car drove by her and blew its horn. Odd, she thought, as the car then pulled into a church parking lot and idled. As McVey pedaled past the parking lot, she was yanked from her bike by what she thought was a gang of men, and forced into the car. She soon realized she was alone with a lone stranger.

The stranger blindfolded her and pressed a gun to her head, threatening to kill her if she didn’t comply with his every command. He took her to an apartment and proceeded to rape her repeatedly over a 24-hour period.

Fearing for her life, McVey tried to appeal to her kidnapper’s ego—and the speck of humanity she hoped he had. She had to get home to care for her sick father, she told him, but she knew he was a good guy deep down, and she wanted to be his proper girlfriend. She promised she wouldn’t tell anyone what happened.

The tactic worked, and McVey was deposited by the kidnapper near her home. Police investigating the kidnapping didn’t think to connect it to the serial slayings that had been plaguing the Tampa area since spring of that year. Those victims were mostly prostitutes, whose bodies were cropping up in vacant lots and wooded areas on the outskirts of town. In most cases, the victims had been bound and strangled. Distinctive tire impressions and unique red carpet fibers linked the murders, which by Halloween of that year numbered eight.

To the surprise of investigators, lab results from the McVey kidnapping revealed the same unique red fibers, connecting her abduction to the previous murders.

McVey had been smart in multiple respects. During the ordeal, she noted every detail she could: the make and model of her captor’s car, the color of the interior and type of seats, and the fact that he had stopped to make an ATM withdrawal. Investigators compared lists of those who’d made ATM withdrawals that night with registered owners of red Dodge Magnums, and this quickly led them to 31-year-old Bobby Joe Long. A cursory inspection of his vehicle revealed the same distinctive tires that had left impressions at multiple body dump sites. Police descended upon Long as he was leaving a matinee showing of the Chuck Norris film “Missing in Action.”

The details of Bobby Joe Long’s life forecast his future behavior. Throughout much of his childhood, Long had slept in the same bed with his mother, a barmaid who dressed provocatively and brought home strange men on a regular basis. Born with Klinefelter syndrome, Long began developing breasts as a teenager. He had also suffered multiple head injuries, as both a child and an adult, the most severe being a motorcycle accident that plunged him into a brief coma, from which he awoke with an insatiable sexual appetite. It was the textbook perfect storm of factors that led to him being a domestic batterer, and it was the dissolution of his marriage that paved the final stretch of road to his homicidal crime spree.

After being confronted with the evidence, Long confessed, not only to the Tampa serial murders but also to a series of assaults in South Florida in which he would respond to classified ads and then rape the women he found home alone.

Bobby Joe Long was on Florida’s death row since 1986, and executed by lethal injection on May 23 of this year. Surviving victim Lisa McVey now works as a sheriff’s deputy for Hillsborough County.

OTTIS TOOLE

Ottis Toole (Candace West/KRT/Newscom)

Ottis Toole was a lifelong transient whose velvety unctuousness would make even an armadillo’s skin crawl. A kind of parasitic shadow human, Toole’s name almost never appears outside of two contexts: the infamous 1981 murder of Adam Walsh, and as the partner in crime to murderer Henry Lee Lucas.

Toole was born March 5, 1947 in Jacksonville, to an alcoholic father who deserted his family after the birth of Ottis, their fifth child. He grew up in a low-income neighborhood and was raped regularly from the age of 6 by a family friend. Meanwhile, his unfit mother frequently dressed him in girls’ clothing. A pyromaniac and serial arsonist by the time adolescence arrived, he dropped out of school in the ninth grade. Barely literate and borderline mentally retarded, Toole—by his own account—became a male prostitute and killed his first victim, a would-be client, at the age of 14.

Toole hitchhiked the U.S. throughout his 20s, returning to Jacksonville in 1975. There, he met a fellow drifter named Henry Lee Lucas at a soup kitchen. The two became lovers and lived together at the home of Toole’s parents, where Lucas befriended Toole’s intellectually impaired niece, Becky Powell.

In the early 1980s, Lucas traveled with Powell to California, where he ended up working for and living at the residence of 82-year-old Kate Rich. After being caught defrauding her, Lucas murdered the elderly woman and then fled to Texas, where he killed Powell during an argument. He was eventually taken into custody and confessed to those and hundreds of other murders, implicating his companion Ottis Toole in many of them.

Around the same time, Toole was charged with arson and murder in the death of George Sonnenberg, whom he’d trapped inside a house before setting it ablaze. Following Henry Lee Lucas’s example, Toole also began confessing to multiple crimes. Among them was the murder of Adam Walsh.

People search for Adam Walsh’s remains at the Florida Turnpike in 1983. (Credit Image: Palm Beach Post/ZUMAPRESS.com)

Their confessions thrust the two men into the global spotlight as perhaps the most prolific serial killers in U.S. history. But Lucas may have ultimately been purely a serial confessor, and not a serial murderer, and Toole likely emulated this baseless braggadocio. It’s perhaps no coincidence that Toole first implicated himself in the Walsh murder the day after a TV movie about the Walsh case had aired, which Toole may have watched in prison.

Toole, who died in 1996, was officially named the murderer of Adam Walsh in 2008, and the Hollywood Police Department formally closed the Walsh case. However, some problems remain with Toole’s candidacy.

Largely lost to time are descriptions of a muscular, mustached olive-skinned man in his 20s, who had been seen in the parking lot outside the Sears from which Adam went missing, forcing the boy into a blue van—one that matched the description of a van seen parked late at night near the Turnpike mile marker where Adam’s severed head would later be discovered. A man was observed walking toward the canal bank with a bucket in hand.

Two separate composites were generated from the accounts of two distinct witnesses—one an adult, and one a child. The sketches closely resembled each other, and tend to rule out Ottis Toole as the individual observed.

DANNY ROLLING

Danny Rolling is led from holding cell after a competency hearing.

In late summer 1990, as the University of Florida was oiling the gears for its fall semester, a dark force crept into the Gainesville area in the form of a hulking 36-year-old drifter from Louisiana named Danny Rolling. Fresh off the Greyhound bus from his hometown of Shreveport, Rolling pitched a tent in the woods near the University of Florida and began prowling and peeping into the windows of nearby student apartments.

This proclivity was familiar for Rolling, a seasoned criminal who’d served a collective eight years for multiple armed robberies and escaped from prison twice. He was also an accomplished burglar. And a rapist. And, by the time he arrived in Gainesville that summer, a multiple murderer.

The primary antagonist in Rolling’s life had been his brutish father, who had physically and emotionally abused Danny beginning in early childhood. During a heated argument on May 18, 1990, Danny seized his father’s handgun and shot him in the stomach and between the eyes. The elder Rolling survived, and Danny fled the area with a stolen identity, crime-spreeing his way to Florida alternately on buses and in stolen vehicles. Now smoking crack and subsisting on armed robberies, Rolling was a loose cannon of the most terrifying kind.

The footprint of Rolling’s presence in Gainesville first became evident on the afternoon of August 26, when authorities found the bodies of 17-year-old University of Florida freshmen Christina Powell and Sonja Larson inside the apartment they shared. Both had been raped, stabbed to death and posed. The next day, the decapitated body of Christa Hoyt, 18, was found posed in a sitting position on her bed, with her excised nipples beside her and her head on a nearby shelf.

The 34th Street Memorial in Gainesville, Florida with the names of Danny Rolling’s victims.

The same day Hoyt was discovered, Rolling gained entry into the apartment of Manuel Toboada and Tracy Paules, both 23. Rolling first killed Toboada before heading upstairs, where he bound, raped and fatally stabbed Tracy, whose body he posed before exiting.

Rolling was arrested the following month while fleeing the attempted robbery of a Winn-Dixie store, and police noted he was wanted in Shreveport, where a triple murder he committed exhibited similarities to the Gainesville crimes. His DNA was collected and was ultimately matched to all of the Gainesville murders.

While awaiting trial, Rolling began courting a self-described true crime journalist named Sondra London, who was a bridge to another of Florida’s most prolific serial murderers: Gerard John Schaefer, a one-time sheriff’s deputy responsible for the deaths and disappearances of dozens of women. (London had dated Schaefer when the two were still in high school, later reconnecting with him as he served out a life term.) Rolling and London claimed to be in love and became briefly engaged, while Schaefer fumed over the perceived betrayal. Schaefer was murdered by a fellow inmate in 1994; Rolling was executed by lethal injection in 2006. London remains single.

This story is from the July/August 2019 issue of Boca magazine. For more content like this, subscribe to the magazine.