The Sinister Double Life of Dr. Glennon Engleman: From Dentist to Contract Killer
Dr. Glennon Engleman might have looked like any other neighbourhood dentist, but behind that ordinary exterior was one of Missouri’s most calculating killers. Born on February 6, 1927, in Saint Louis, Missouri, Engleman, known as Glen to his friends, grew up in a south-side neighbourhood and felt deeply connected to his community. After serving in the military, he used the GI Bill to attend Washington University and become a dentist, opening his practice on his home turf. But for Glen, dentistry was never enough; he harboured a secret life steeped in violence and profit, built on a series of cold-blooded murders where life insurance payouts were often the only motive.
Early Life and Career Beginnings
Glennon Engleman’s life began humbly. Raised in a working-class area of Saint Louis, he learned the values of hard work and resilience. His decision to pursue dentistry was more pragmatic than passionate; it allowed him a stable income and respected position in society. To most of his patients, he was simply Dr. Engleman, the man they trusted with their teeth. His private life, however, was a web of relationships, lies, and calculated schemes.
In the early years, Engleman married Edna Ruth but quickly found himself disillusioned with the relationship. They divorced in 1956, and two years later, both had remarried. Glen’s new wife was Eda, while Edna Ruth married James Stanley Bullock, a young man who had served in the military and returned to Saint Louis to work and go to college. But only six months into their marriage, James Bullock was dead, and suspicions arose around Edna Ruth and Glen Engleman.
The Mysterious Death of James Bullock
On December 17, 1958, citizens near Forest Park in Saint Louis spotted a man, bloodied and stumbling. The man, identified as 28-year-old James Stanley Bullock, had been shot. He died from his injuries, leaving police with no suspects or clear motive. At first, no one suspected Edna Ruth or her former husband, Dr. Engleman. But as the investigation unfolded, authorities learned that Edna Ruth had taken out multiple life insurance policies on James, worth a total of $64,088—a small fortune in 1958.
When police questioned Edna Ruth, her responses were odd. She admitted that she’d been married before but that her new husband, James, was unaware of her past with Dr. Engleman. She had lied on her marriage application, concealing her previous marriage to Glen. Edna Ruth and Glen refused to take a polygraph test and denied any involvement in the murder, and despite these suspicions, no charges were ever filed. Instead, Edna Ruth took her payout and invested some of it into Dr. Engleman’s dental practice.
The Death of Eric Frey and the Beginning of a Pattern
The next incident came just five years later. Dr. Engleman had grown close to Eric Frey, a business associate with whom he co-owned a drag racing strip. In September 1963, they were at the strip, using dynamite to clear abandoned cisterns. According to Engleman, the dynamite detonated unexpectedly, killing Eric Frey instantly. His body was found in the bottom of the cistern, and while his death was officially ruled accidental, suspicions lingered. Frey’s widow, Sandy, had a substantial insurance policy on her husband, and as with Edna Ruth, part of this money found its way back into Engleman’s dental practice.
This was the beginning of a chilling pattern: people close to Engleman would die, often under suspicious circumstances, and insurance money would subsequently fund his ventures. Engleman had essentially found a side business, one built on murder and insurance fraud.
Complex Marriages and Murders
By 1967, Engleman had divorced Eda and married a third wife, Ruth. While they shared a son, Ruth grew uncomfortable with her husband’s close relationship with a young woman named Carmen Miranda, whom he trained as a dental assistant. Ruth suspected flirtation between Engleman and Carmen but held her suspicions to herself. Soon, however, Carmen married Peter Halm, a decision that appeared orchestrated by Engleman himself.
In 1976, while walking in a rural area with Peter Halm, Carmen became the sole witness to her husband’s sudden death. Peter was shot in the head, reportedly by a stray bullet in a hunting area. Authorities found an ‘X’ made from tape on a nearby tree, raising the theory that the shot was deliberate, targeting Peter as he stood near the marked spot. As with previous victims, Carmen received a sizable life insurance payout, part of which supported Dr. Engleman.
Glen married Carmen soon after her husband’s death, establishing another marriage marred by tragedy and suspiciously linked insurance money.
The Gusewelle Family Murders
The most devastating chapter in Engleman’s career came in 1977 when he targeted the Gusewelle family. Arthur and Vernita Gusewelle, a wealthy farming couple, were killed in their home in Edwardsville, Illinois. Arthur having been shot and Vernita having been bashed to death. Seventeen months later Engleman murdered the Gusewelles' son Ronald in East St. Louis, Illinois, in order for his widow Barbara Gusewelle Boyle to claim the millions in life insurance she had taken out on her husband Ronald, who was the sole heir to his parents' oil business.
Boyle collected approximately $340,000 (equivalent to $1,710,000 in 2023) following her husband's murder. Boyle was convicted in her husband's murder but was acquitted of killing his parents. She was subsequently sentenced to 50 years in prison for the murder of her husband.
The Murder of Sophie Barrera and Engleman’s Downfall
By 1980, Engleman’s streak of murders seemed endless, yet he had evaded the law at every turn. Sophie Barrera, a dental lab owner who had supplied Engleman’s practice, became his next target after filing a lawsuit against him over unpaid bills. On January 14, 1980, Sophie’s car exploded, killing her instantly. Police, well aware of Engleman’s reputation, considered him the primary suspect but lacked sufficient evidence.
Eventually, his ex-wife Ruth agreed to cooperate with the authorities. She explained that Glen had confessed multiple murders to her during their marriage, bragging that he could kill without remorse. Ruth agreed to wear a wire, and after numerous attempts, Engleman made incriminating statements that linked him to several murders. This evidence finally led to his arrest.
The Trials and Convictions
Dr. Glennon Engleman’s trial captivated the public. It was revealed that he had used his charisma and position as a respected dentist to exploit, manipulate, and ultimately kill those who trusted him. He was convicted of multiple murders, including the deaths of Peter Halm, Sophie Barrera, and the Gusewelle family. Sentenced to life in prison without parole, Engleman faced additional charges for federal mail fraud, linked to the insurance claims he orchestrated over the years.
His case revealed the extent of his greed-driven violence. While some killers act out of rage or psychological compulsion, Engleman’s motives were chillingly financial. His murder victims were pawns in his schemes, lives reduced to dollar signs and insurance policies.
The Aftermath of the Double Life of Dr. Glennon Engleman
Dr. Engleman’s patients knew nothing of the sinister motivations behind his seemingly compassionate care. Yet Engleman, a man who found murder “more sexually satisfying than sex,” harboured no remorse, finding perverse enjoyment in his crimes.
Engleman died of diabetes-related complications in prison in 1999. His life left behind a trail of devastation and unanswered questions, with many wondering just how many lives he ended. Known to have killed at least twelve people, Engleman’s actual toll may never be known.
In his own words, Engleman was “homicidally intimate,” a term that underscored his unique and disturbing satisfaction from the act of murder. Today, the name Dr. Glennon Engleman serves as a chilling chapter in the history of American crime—a story that continues to fascinate for its twisted combination of respectability and ruthlessness.