Bad Luck Betty: The Case of the Black Widow Granny

She was called the “Black Widow Granny” in a media frenzy that began as soon as Betty Neumar was arrested at the age of 76. She looked like your everyday grandma – harmless. But once investigators started unraveling Betty’s life, more and more questions were raised (as well as eyebrows). Betty had been married five times (at least as much as we know) and used at least 28 aliases throughout her life.

Al Gentry / Betty Neumar / Harold Gentry, Betty Neumar / John Neumar, Betty Neumar.
Source: YouTube

But the most remarkable part of Betty’s life is the fact that all her husbands died under strange and mysterious circumstances. So, did Betty just have the worst luck in the world? Or was she the mastermind of a dark game of love and death?

Husband #1: The Highschool Sweetheart

She was born Betty Johnson in 1931, in Ironton, Ohio. Being a child of the Great Depression, her childhood was anything but ideal. She was born into poverty, and what that meant for other young women like her was that if she wanted to make it out of the gutters, she was going to have to marry. And marry well.

A portrait of a young Betty.
Source: Tumblr

She finished high school in 1949 and married her boyfriend, Clarence Malone, a year later. Clarence was a mechanic. Their marriage was short-lived, and in court records, Betty claimed that he was abusive towards her. They separated in December of 1951, a year after the wedding. They managed to have a child together, Gary, who was born three months after their split.

Husband #2: The First Mysterious Death

It didn’t take long for Betty to marry her next husband, James Flynn. Flynn legally adopted her son Gary but there aren’t any public records of their marriage. More so, not much is known about James and Betty’s marriage. We do know that they had a daughter together, named Peggy.

A picture of Betty Neumar, Gary, and Peggy.
Source: Cecelia Flynn

Like her first, this second marriage was short. But James was the first mysterious death to befall Betty. Betty claimed that he died somewhere in New York in 1955. She told investigators that he “died on a pier” after freezing to death in his car. According to other records, James was shot dead on that pier.

Husband #3: The Drunken Sailor

Nevertheless, Betty moved on, as one does. She relocated to Jacksonville, Florida, with her children and started going by the name Betty Flynn, even though James was no longer around. It was 1960, and Betty enrolled in beauty college to begin working as a beautician.

A room at beauty college.
Photo by Found Image Holdings/Getty Images

In 1965, when Betty was in her early thirties, she met and married her third husband, Richard Sills – a Navy man. Richard was recently divorced but wasn’t in contact with either his ex-wife or his son. His and Betty’s marriage also seemed to be rocky. Betty’s daughter Peggy said what she remembered most about Richard was his heavy vodka drinking and that he and her mom fought a lot.

A Gunshot in the Bedroom

In 1965, the same year as their wedding, the couple was arguing in their trailer home in Big Coppitt Key, which is located on an island in the Florida Keys. They were arguing in their bedroom while 11-year-old Peggy was in the other room.

A vintage trailer home interior.
Photo by Stuart Lutz/Gado/Getty Images

Peggy recalled them fighting and suddenly hearing a gunshot. By the time she went into the room to see what had happened, paramedics had already showed up. She asked them if Richard was dead. According to her mom, they were arguing, but Richard was intoxicated and shot himself.

Was It Really Suicide?

Richard’s death was ruled a suicide, and because of that, all the records about his death were destroyed long before investigators reopened the case. Local law enforcement weren’t the ones to handle the investigation into Richard’s death. It was turned over to the NCIS, the Naval Criminal Investigative Service.

The door to the city morgue.
Photo by Robert Simmons/Pix/Michael Ochs Archives/Getty Images

There happened to be some discrepancies between the two agencies. While no autopsy was ever conducted on Richard, the Florida Medical examiner said he died from a single gunshot wound to the chest. The NCIS, on the other hand, reported two wounds…

It Was Too Late

The NCIS found that Richard was shot twice: once in the chest and once in the heart. Betty never informed Richard’s son or ex-wife; she left that to the military, which showed up at their home and told them. By the time investigators opened up the case in 2009, it was too late – Florida’s statute of limitations had already expired, and Richard was never exhumed.

A portrait of Betty Neumar.
Source: Pinterest

After the authorities closed the case, Richard’s son, Michael Sills, asked the NCIS cold case squad to look into it. But again, it was too late, and soon you’ll understand why…

Husband #4: The Retired Marine

Three years after Richard’s death came husband #4. In 1967, Betty met Harold Gentry, who had been stationed in Florida. The two met while she was working as a hairdresser. Within a year, the couple were walking down the aisle. By 1969, they had their daughter, Kellie.

A picture of Harold at home.
Source: YouTube

The family moved around a lot, and after 21 years in the service, Harold finally decided to retire. They settled in Harold’s hometown of Norwood, North Carolina. They built a home on land that had been gifted to them by Harold’s sister.

While Married to Harold, James Gets Shot

It was during her marriage to Harold that Betty’s first husband, James Malone, died. And his death was also under mysterious circumstances. Like Betty, James had also remarried. In Medina, Ohio, on November 27, 1970, James was shot at his car repair shop.

A portrait of Harold and Betty.
Source: Pinterest

It was a random, drive-by shooting. No one was ever a suspect or arrested in the case. While Betty was never accused of involvement in the murder, it only raises eyebrows about the overall mystery of her lethal love life. After all, she was married to her fourth husband and seemed to be happy…

The Brother-in-Law Had His Suspicions

Betty and Harold seemed to be living a normal life in a loving marriage for many years. Harold’s brother, Al Gentry, had something to say about it, though. Al said that the couple was broken beyond repair after 18 years.

A still from Al Gentry during an interview.
Source: BBC News

He claimed that his brother and Betty had separated in 1986, after which Betty went to live in Florida for several months. During their separation, Harold met another woman. According to Al, Harold told Betty that he was leaving and starting the divorce process.

Harold Gets Shot in His Own Home

Less than two weeks later, Harold was shot six times as he walked into his home. At the time, investigators believed Harold stumbled upon a robbery since the house was ransacked. But Al doesn’t believe it was just a matter of being in the right place at the wrong time; he thinks Betty hired someone to kill Harold.

Harold’s home in North Carolina.
Source: Norwood Police Department

Al was the one called to identify Harold’s body since Betty was a three-hour drive away in Augusta, Georgia. Al was sure that Betty was involved when he saw her behavior upon arriving at the scene.

Her First Son Takes His Life

Betty allegedly had no tears, no emotion, and said she couldn’t have been involved since she was in Augusta without being asked. Harold’s murder was also lacking evidence and suspects, and thus it went cold pretty quickly, like the cases of her previous husbands.

An elderly Betty takes a picture with her daughters.
Source: Tumblr

Betty was, yet again, cleared of any wrongdoing. And, of course, she moved on. Now in her fifties, Betty moved to Augusta. She opened up her own salon there and continued working as a hairdresser. In 1985, her first child, Gary, committed suicide. Betty was simply bad luck.

Traumatized for Years

According to Gary’s widow, Cecelia, Betty “was not a nice person.” And it was Betty, not Cecelia, who received Gary’s $10,000 life insurance money. Cecilia also said that Gary witnessed Richard Sill’s death, and it was likely the trauma that deeply affected him for years.

A picture of Betty at home.
Source: Pinterest

Without a doubt, it is all very suspicious. It turns out that it wasn’t just her husbands who were dropping like flies. Her own son was added to the death list. But could Betty really want her own son dead? And just to get insurance money? Or did he know too much?

Husband #5: The Lonely Retiree

Betty met John Neumar in her salon in 1990. John was recently widowed with two grown kids and was looking for some companionship. He found Betty charming and was smitten with her. But John’s kids were shocked when he told them less than a year later that he was going to marry Betty – some woman they barely knew.

A younger John sits with his son.
Source: YouTube

After their 1991 wedding, John’s children said their father started to change. Their previously loving and easy-going relationship with their dad grew cold and distant. A major change in that relationship happened in 1995 when Betty convinced John’s son to invest $1,000 of his money in a Ponzi scheme.

Getting Swallowed Into a Ponzi Scheme

As it turns out, Betty also had convinced about 200 others to invest, telling them they would get back $100,000 for every $100 they invested. All this money was funding legal expenses for a rich European family that died without an heir.

John and Betty take a picture on the beach.
Source: Pinterest

The money was meant to be distributed to everyone who had sponsored their lawyers. The thing is, there wasn’t an insane amount of uninherited wealth, so it’s not really clear why and how Betty got involved. But in this particular scheme, seven people were arrested. Betty, however, was not.

From Savings to Bankruptcy

However, something happened to John’s money since the couple was forced to file for bankruptcy in 2000. After a decade of marriage, they found themselves in over $200,000 in credit card debts. It’s just another example of how Betty was bad luck.

John and Betty walk by the beach.
Source: YouTube

Before his marriage to her, John had owned his home, had great retirement savings, and was always good with his money. It was something he passed on to his kids, which is why they couldn’t believe it when they learned of their father’s situation. And nobody knew where the money went or how they ended up in such debt.

Bad Luck Betty Strikes Again

It also didn’t seem as though the money was spent on themselves. It was as though it just disappeared. Then, in 2007, John grew very ill. He had been healthy his entire life, but he was now diagnosed with sepsis. Sepsis is a life-threatening condition that causes damage to the body’s tissues and organs.

John’s son speaks in an interview.
Source: YouTube

John deteriorated very quickly. In fact, his kids didn’t even know he was sick. When he died not long after his diagnosis, at 76, Betty didn’t tell her his children that their father had passed away. John’s son learned of his father’s death while at work, reading the newspaper’s obituaries.

Cremated, Just in Time

John Neumar Jr., the son, confronted Betty about his father. That’s when he learned that she chose to have him cremated. They were stunned, seeing as John was Catholic and never intended on being cremated upon his death.

Betty talks about John as she goes through old pictures.
Source: YouTube

John Jr. had already purchased his funeral plot next to his mother, John’s first wife. The family then went to the police to ask questions, discovering that John’s cause of death was determined to be natural causes. That means no autopsy was performed before his cremation. Again, it was too late to investigate any further.

Reopening the Cold Cases

In 2007, Al (Harold’s brother) managed to reopen his brother’s cold case in North Carolina. Once the case was open again, law enforcement agencies connected with Georgia’s authorities to re-examine both Harold and John’s deaths.

Al stands in his garage during an interview.
Source: YouTube

A search warrant was finally issued, and for the first time ever, detectives searched Betty’s home. What they found may not be surprising to us now, considering her past, but to locals and people who knew of Betty, it was the last thing they expected. What they found in her home was incriminating.

Searching Betty’s Home

The police found numerous varieties of poisons in Betty’s home, including arsenic-based rat poison. They also found an extremely poisonous liquid called carbon tetrachloride, which was an odd find since the bottle was empty…

A view of a Carbon tetrachloride bottle.
Source: YouTube

Carbon tetrachloride is a colorless liquid that has a gentle, sweet odor. If one is exposed to the chemical, it can cause liver and kidney failure as well as gastrointestinal and neurological symptoms. Yup, you guessed it: these were very similar symptoms to what John experienced before his death. If it isn’t clear by now, Betty was becoming a suspect in her husbands’ deaths.

Betty, You’re Under Arrest

John’s cremated remains were also examined, and what they found were traces of heavy metals. But John had been on multiple medications, so some of those medications could explain the metals in his system. All in all, it was too late to get a definitive conclusion.

A still from Betty at the police station.
Source: YouTube

Still, there was enough to place a charge on Betty. She was arrested in May 2008 for the “solicitation to commit first-degree murder.” Reportedly, officers found enough evidence to show that she had attempted to hire three separate people to kill her then-husband, Harold Gentry.

Easier to Kill Than Divorce

Betty was 76 at the time of her arrest and put on a $500,000 bond. How did it take so long to even suspect her? Who knows? But police figured Betty learned early on in her marriage “career” that it was easier to kill than divorce.

A portrait of Betty after her arrest.
Source: YouTube

Money didn’t seem to be a motive, though, as she didn’t get much insurance money from her dead husbands. She later said in an interview, in response to being accused of killing for insurance money, “I got no insurance from the first one, no insurance from the third one.”

Money Wasn’t the Motive

“After Harold died, I got $50,000. But as far as all this money and all this stuff goes, there wasn’t none.” She ultimately spent a number of months in jail but got released once she posted a $300,000 bail. Her daughters, Peggy and Kellie, believed in their mom’s innocence.

One of her daughters speaks during an interview.
Source: YouTube

“She has been a caring, loving mother, and she’s a loving, caring grandmother. I think that she was dealt a bad hand,” Peggy stated. Betty maintained her innocence all the way up to nearly receiving her trial date. But here’s the thing: she never made it to trial…

No Deathbed Confessional

Before she was even given a trial date, Betty died of cancer. It was 2011, and she was 79 years old. So, what happens then? Is she simply acquitted since she’s no longer alive? After her death, the states involved in the cases closed their files. But that’s not to say that questions were answered.

A mugshot of Betty.
Source: YouTube

Since the men in Betty’s life all died under mysterious circumstances, people were hoping she would fess up before she died. Police, for one, hoped for a death bed confessional. Betty died on June 13, 2011, at a hospital in Louisiana.

Searching for Answers

Buried with her are all her secrets. Michael, Richard’s son, still wants his father’s body exhumed. Michael believes that his father’s death is the only one with the potential to draw a definitive answer. He was disappointed when the NCIS dropped the case after Betty’s death.

A still from Betty during an interview.
Source: YouTube

Beyond disappointed, Michael was enraged that Florida authorities refused to investigate his father’s death any further. It wasn’t until 2008 that he even realized that he could have gotten a chance to meet the father he never knew. His parents had divorced when he was a toddler.

Too Many Inconsistencies

Michael said his father’s military file isn’t one that portrays a man who would commit suicide. “As far as I’m concerned, she did it,” he said in an interview. “There’s too many inconsistent things about it.” As for Al Gentry passed away in 2013 after fighting for his brother’s murder case for 25 years.

A portrait of Harold and Betty.
Source: Pinterest

Al was dedicated and continued fighting even after Betty’s death since the shooter is still at large. He even found her death suspicious, suggesting that she might have faked her own death. “It’s like her to try some scam like that,” he said. “I wouldn’t put it past her.”

Grandma in Jail Garb

You see, Betty’s final years likely would have remained under the radar were it not for Al. Thanks to him, people learned more about the gray-haired grandma standing in court in the classic orange jail outfit.

A still from Betty at the police station.
Source: YouTube

Al was always suspicious of his sister-in-law with her cold demeanor, especially after Harold’s death. Al suspected that his brother was murdered because he knew too much about Betty’s immoral activities. He also believes that she was trying to collect his insurance policy before he got the chance to divorce her.

“Never Trust That Woman”

“He told me just before he died,” Al said in an interview, “Never trust that woman. She isn’t who she says she is.” Once the police started probing Betty’s life, they discovered things that raised even more questions.

A portrait of Betty during an interview.
Source: YouTube

Like why would a beautician and former bus driver need several driver’s licenses from different states? And why so many passports and credit cards in other people’s names? She even had two bank accounts in Germany. No ordinary person has that many identities. And this was no ordinary old lady.

He Got “Ripped Off”

Before Betty died, the court proceedings were delayed numerous times. Still, Al – for one – was hopeful that she would finally face charges later that year. He said he feels “ripped off” that she died before facing charges for his brother’s death.

A still from Al during an interview.
Source: YouTube

After getting charged, Betty refused to speak to reporters. She did, however, cooperate with the BBC for a documentary they aired in November 2009. In the interview, she said her accusers were “nuts.” Her lawyer, Charles Parnell Jr., chose not to participate.

The One Brother Who Doesn’t Blame Betty

Remember Betty’s first husband, Clarence Malone? The one that got shot 18 years after he and Betty divorced? Well, one of his brothers told the Associated Press that he didn’t think Betty had anything to do with the yet-to-be solved killing of his brother.

The members of a motorcycle gang.
Photo by MediaNews Group/Oakland Tribune/Getty Images

Apparently, there were rumors that Malone got some members of a local motorcycle gang angry. He was 38 years old at the time, and the one-page incident report (released by the Medina County Sheriff’s Office) contained few details about the murder. Betty told investigators that he had died of cancer…

Reopening Gary’s Case

The Lake County Sheriff’s Office decided to reopen the investigation into Gary Flynn’s suicide in 1985 once his mother was charged. Detective Scott Stranahan eventually concluded that Gary’s death was indeed suicide.

Investigators interrogate, looking for answers.
Source: YouTube

Gary had been living in Lake County, working at a nuclear power plant while his wife and kids were in Michigan. Still, there are some family members who are skeptical about whether he actually took his own life, despite the fact that Gary left a suicide note. And it’s because his mother took the insurance money.

He Had His Own Demons

Jeff Carstensen, Gary’s stepson, told investigators about his stepdad’s childhood recollections of messy alcohol-fueled holiday get-togethers. Gary and his sister Peggy were in the house when Richard was killed in Florida. Jeff also told investigators that Gary was paranoid about banks.

A black bottle and a glass of whiskey.
Photo by Christine von Diepenbroek/Getty Images

Apparently, Gary considered himself a survivalist who would go on the occasional drug and alcohol binge after talking to his mother on the phone. Jeff said that he and his mother, Cecilia, raced from Michigan to Gary’s home before Betty could since they suspected that Gary had a large amount of cash in his house.

Hidden Under His Bed

Jeff said that he and his mother found, hidden under Gary’s bed, $16,000 in cash. With the cash were a cache of guns and ammunition. Betty and her fourth husband, Harold, arrived later that same night. Gary’s body was cremated the day after he died, and Betty took the urn with his ashes home with her to North Carolina.

Cash is found under a bed.
Photo by patty_c/Getty Images

Two years later, Jeff, who was newly divorced, moved to Augusta to live with Betty. He returned to Michigan a year after, he said, because he feared for his life.

He Beat Her to the Punch

According to Jeff, Betty got him fired from both his jobs and also ruined his relationship with his girlfriend. She offered to take a $100,000 life insurance policy on him. Jeff thought that Betty “intended to harm him to collect the life insurance, so he decided to move back to Michigan,” as Detective Stranahan had written in his 2008 report.

A portrait of Betty Neuman.
Source: Pinterest

Jeff ended up passing away five days before his grandmother. He was 44. His relatives reported that he died in his sleep. The Monroe County in Michigan didn’t report on his official cause of death.