Florida Realtor's Headless Body Found In River Connected To Suspected Serial Killer

Margo Dilemon, a realtor, went to meet a prospective client — but was never seen alive again. Her disappearance led detectives on a hunt filled with shocking twists and turns.

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Margo Delimon's Coworker Recounts "Threatening Man" Who Visited Model Home
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Margo Delimon's Coworker Recounts "Threatening Man" Who Visited Model Home

Gwynne Sams worked with Margo Delimon at a model home at the time of Margo's disappearance. Sams tells the story of seeing a suspicious and "threatening" man at the model home.

Professional life in Pinellas County, Florida was going well for wife and mother Margo Delimon. She’d moved to the area to get in on the booming real estate industry, and the move was working out. However, her promising career would be cut short by a vicious serial criminal.

On the morning of October 3, 1981 Margo was scheduled to show a few homes to prospective buyers. However, when the couple got to the real estate office, they found Margo’s car — but no Margo. Once her coworkers caught wind of what had happened, they were worried: Margo was known for keeping her appointments. They began calling around in an attempt to find her, but were unable to reach Margo’s husband, Bob.

Finally, after two days had passed with Margo’s car abandoned in the parking lot, they filed a missing person report.

“She just disappeared while she was on the job. We thought, there’s no doubt this was a suspicious disappearance,” Everett Rice, Chief of Detectives for the Pinellas County Sheriff’s Office, told Oxygen’s “Buried in the Backyard,” airing Thursdays at 8/7c on Oxygen.

Authorities examined Margo’s car, finding it unlocked but in normal condition, and talked to her coworkers, who said they last saw her on the evening of October 1. They also learned she was estranged from her husband, Bob, who was out of town at the time of her disappearance while visiting his mother in New York. Margo’s daughter, Didi, meanwhile, was living with Margo’s parents in Texas.

“Of course, we were very concerned about Margo. It’s just not like her to disappear. I had a bad feeling about the whole thing,” her sister, Marsha Cruz, told producers.

Investigators traveled to the apartment Margo and Bob shared, but found everything in its place with no obvious signs of a struggle. They then reached out to Bob, who told them over the phone he’d last spoken to Margo the night before she vanished and everything had seemed normal. Still, authorities were suspicious of Bob and asked him to return to the area.

Margo’s parents rushed to Florida, where they put an ad out in the local paper, asking the public for any information they may have regarding their daughter’s disappearance. It wasn’t long before someone who knew Margo and Bob called to report they once heard Bob say that if Margo ever left him, he would kill her.

Margo and Bob had indeed been having problems, her family told producers: Bob did not want to work and Margo was frustrated by his lack of contribution to the household.

As soon as he returned from New York, Bob was summoned by the authorities for questioning. He claimed he and Margo were trying to work on the issues in their marriage. Still, authorities asked Bob to take a polygraph test.  He obliged — and passed. They had to consider other possible suspects.

Authorities spoke to Margo’s co-workers again, who told them the night before she went missing, Margo had a date scheduled with a man named Don. When investigators located Don, he admitted to planning a date with Margo the night before she vanished, but said he decided not to go and instead stayed home with his wife.

“When we found that he was married, that obviously seemed very suspicious,” Detective Mike Madden with the Pinellas County Sheriff’s Office told producers.

But Don also passed a polygraph test, and his wife confirmed his alibi, leaving investigators back at square one.

Then, nearly three weeks later, a disturbing discovery changed everything. A couple fishing along the Withlacoochee River were stunned when their dog ran off and uncovered a dead body. Citrus County authorities rushed to the scene, where they found a body with no head in an advanced state of decomposition.

“This isn’t your typical type of killing,” Fred Schaub, lead prosecutor in Pinellas County, told producers. “This was a heinous crime. We needed to find the person responsible.”

Authorities transported the remains to a medical examiner, who concluded the body belonged to a young female and had been there for months. However, they said the body did not belong to Margo.

Authorities thought it could have been the remains of a young Black woman who had been reported missing in Citrus County months earlier. But when testing showed it was not that woman either, authorities grew increasingly disturbed and began to wonder if there was a serial killer on the loose.

Four different women had all gone missing from neighboring counties in recent months: On September 1, 1980, a night clerk named Cynthia Clements went missing. Her body was found in a wooded area six months later. A week after Clement’s disappearance, 19-year-old Elizabeth Graham, a dog groomer, vanished after going on a house call. Eight months later, another young woman, Barbara Barkley, went missing after heading to her job at a furniture store. Four months after that, Margo disappeared.

“This was a really frightening time in Florida,” Marcia Crawley, a former journalist with WFLA-TV, recalled.

Three months after Margo’s disappearance, another break in the case came when local authorities received a call from detectives in Orlando, who reported a real estate agent was just abducted there. They said a male suspect had told a female realtor he wanted to look at a few houses, and she got in his car with him to show him the properties. He then abducted her at knife point. Fortunately, the woman was able to escape when her abductor stopped for gas. After a chase, that man was arrested. 

Authorities in Orlando noticed the similarities in their case and the disappearance of Margo Delimon, another local realtor.

A fingerprint check showed the man who’d abducted the realtor from Orlando was named James Delano Winkles, a resident of Pinellas County. He’d recently gotten into trouble for trying to sell land that did not belong to him — the same land where the fishing couple had found the headless body.

Authorities from Pinellas County traveled to Orlando to interview Winkles, but he refused to talk to them. Although he was convicted of abducting the realtor in Orlando, authorities were unable to link him to any of the disappearances.

Seven months after Margo’s disappearance, another gruesome discovery led to progress in Margo’s case. On May 24, 1982, Buck and Geraldine Hope were picking blackberries with a friend on their expansive property. The couple’s son, a realtor named Charles Hope, had gone missing less than two months ago, so when they found a human skull nestled among the blackberry bushes, they feared the worst.

The skull had no mandible or teeth, and there were three vertebrae attached. A DNA test showed that the skull did not belong to the couple’s son, but the vertebrae were matched to the headless remains found along the Withlacoochee River.

In August 1993, authorities in Pinellas County went to Citrus County to compare fingerprints of their missing person cases to what had been found in Citrus County. Fingerprints showed that those remains found in the river did, in fact, belong to Margo. Seven months after her disappearance, authorities finally learned what had happened to Margo Delimon.

With Margo’s remains identified, authorities set to work identifying a killer. Winkles was the most obvious suspect — however, detectives did not have any evidence linking him to the crime.

It wasn’t until February 1998 when investigators received a shocking call informing them that an inmate at the state prison wanted to confess to unsolved homicides. It was Winkles. At that point, he was serving a life sentence plus 90 years for the abduction of the realtor in Orlando. When he spoke to investigators, he confessed to the abduction and murder of Margo Delimon.

He said he’d seen her at the real estate office and had asked her if he could meet her to look at some houses the next day. That morning, she met him at the office and got into his car with him. He took her to his grandmother’s home, where he kept her for several days. He had told her he wouldn’t kill her if she had sex with him, but once he realized that she would be able to lead authorities back to his grandmother’s home, he decided he had to murder her, so he gave her a lethal dose of sleeping pills.

Once she wass dead, he buried her near the Withlacoochee River. Wanting to keep authorities off his scent, he removed her head and then removed the mandible and teeth from her skull so that it would be harder to identify her. It was just an unfortunate coincidence that the place where he tried to dispose of Margo’s skull was the backyard of a couple dealing with the disappearance of their son.

“James Winkles had no connection to the Hope family. It was just a wooded backyard off the interstate,” Schaub told producers.

As authorities continued to interview Winkles, he eventually confessed to the abduction of Elizabeth Graham, the young dog groomer who vanished. He took authorities to another local river and led them to her skull. DNA tests showed that it was a match to Graham.

Winkles was also a suspect in the other slayings, but he refused to admit to anything else.

Winkles was indicted in March 1999 for the murders of Margo Delimon and Elizabeth Graham. He pled guilty to both counts of first-degree murder and was sentenced to death. However, he died on death row in September 2010 before he could be executed.

Today, those who knew Margo remember her as a bright light, but mourn the injustice of her murder. 

“I miss Margo’s kindness,” Cruz said. “She was just always there when I needed her.”

For more information on this case and others, watch “Buried in the Backyard” any time at Oxygen.com.

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