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The Serial Killer Dentist of St. Louis: Glennon Engleman

Dr. Glennon Englemann was born February 6th, 1927, in Saint Louis, Missouri. Dr. Engleman grew up on the south side of the city and felt a deep connection to his neighborhood. After serving in the military, Dr. Engleman used his GI bill to go to Washington University and become a dentist. He opened his dental office on the south side of St. Louis, serving the community he had always loved.

Dr. Engleman, who went by Glen, was married to a woman named Edna Ruth, but they divorced in 1956. By 1958, both Glen and Ruth had remarried. Glen was operating his dental office and appeared to be successfully serving the St. Louis community. On December 17th, 1958, citizens in Forrest Park noticed a bloodied man stumbling. The man, James Stanley Bullock, soon passed from his injuries. These injuries were caused by a gunshot.

No one could figure out why someone would shoot twenty-eight-year-old James Bullock. James Bullock was born April 17th, 1931, in DeSoto. He was raised in Shiloh, Illinois, by his grandparents and later his aunt after his parents passed away. According to an article from 1938, the then seven-year-old was living with his grandparents in 1938 and enjoyed attending school and fishing. James later served in the military before returning to St. Louis to work and go to college.

Back in St. Louis, James met Edna Ruth, the ex-wife of Dr. Glen Engleman. The two married, and six short months later, James was dead. An employee at a local sanitarium initially claimed James was there four days before his murder asking to be admitted because he feared for his life. His wife and aunt said this was not true, as the three had dinner together on that night. According to his widow and aunt, James was not afraid for his life, and they knew no one who would want him dead.

However, Edna Ruth benefitted greatly from her husband’s death. Ruth had life insurance policies totaling $64,088. While under questioning, Edna Ruth made several weird statements including telling the police she was married before, but her husband did not know. Who was she married to? Her husband’s dentist, Dr. Glen Engleman. Edna Ruth had lied to James and his family and lied on the marriage application about being married before.

Police questioned a local career criminal, who was out on parole for an assault at the time of the shooting. They weren’t able to definitely tie him to the murder of James, but they did note he lived near Dr. Engleman’s office. Dr. Engleman and Edna Ruth both refused to take a polygraph test and denied any involvement in the murder of James Bullock. Dr. Engleman’s new wife, Eda, refused to be questioned by the police. A patient provided an alibi for Dr. Engleman. However, another witness said that they tried to find someone at the office around that time and the office was empty.

Edna Ruth invested part of the funds she received after becoming a widow into Dr.

Engleman’s practice. The doctor was treating patients and a pillar of his community, despite

whispers that he may have been involved in the death of James Bullock. Dr. Engleman must have

been bored being a dentist, so he often ventured into other areas of business. This included

buying a drag strip along with a partner, Eric Frey. Dr. Engleman had grown to be close friends

with Eric and his wife Sandy.

On September 26th, 1963, Eric and Dr. Engleman were at the drag strip using dynamite to explode and then fill abandoned cisterns on the property. Eric was lying on his stomach near one of the cisterns when the dynamite exploded quicker than anticipated. Eric was killed instantly and found lying in the bottom of the cistern. Coroner H.D. Steinbeck ruled the death accidental. Mr. Frey’s wife had an insurance policy on her husband, which she invested part of into Dr. Engleman’s practice.

Dr. Engleman divorced Eda and married his third wife, Ruth, in 1967. The couple shared a son, but Ruth hated the close relationship her husband had with a young woman who worked in his office named Carmen Miranda. Dr. Engleman offered to train Carmen to be a dental assistant in his office. Edna felt uncomfortable with the flirting between the doctor and his young assistant. Dr. Engleman, however, claimed he was trying to help people in his community. He hired Carmen’s brother, Nick, as well at one point.

Ruth was relieved when Carmen met a married a man name Peter Halm. Just a few months later, however, Carmen and Eric were walking in a rural area in Pacific, Missouri. The couple were exploring an area known to have caves and scenic paths. A shot suddenly fired, hitting Peter in the head. Peter died instantly, and a hysterically Carmen flagged down help. Nearby, police found an X on a tree made with tape. The area was familiar to locals as hunting area and police believed that the shot was accidental. Police believed someone was target shooting at the X and accidently struck Mr. Halm.

Carmen had a significant amount of life insurance on her husband, totaling $60,000. This is equivalent to around $300,000 in 2023. Dr. Engleman and Ruth divorced soon after, at which time Dr. Engleman married young Carmen, who he had known since she was a small child. His son lived with Edna, his ex-wife. Despite being married to Carmen, Dr. Engleman and Ruth still met regularly for sex. Dr. Engleman constantly had extramarital affairs, which included previous affairs with Carmen, Ruth, and even Sandy Frey, the wife of his business associate Eric Frey who was killed by dynamite.

Another of Dr. Engelman’s affairs was with a patient named Barbara Boyle. On November 3rd, 1977, someone pretending to be from the farm bureau walked up to the farmhouse owned by Arthur and Vernita Gusewelle in Edwardsville, Illinois. Soon after entering the home, the elderly couple were attacked, and both were shot in the head. The wealthy couple left $340,000 to their son, Ronald Gusewelle. Guess who Ronald Gusewelle was married to? Barbara Boyle.

On April 4th, 1979, less than two years after the murder of his parents, Ronald Gusewelle was found dead inside his car outside a hotel in East St. Louis, Illinois. The man had been beaten and shot to death. He had been missing for four days when his body was found. Following her husband’s murder, Barbara collected his inheritance in addition to several life insurance policies. The equivalent sum of money today would be nearly 1.7 million dollars. Guess who she gave a cut to… Dr. Glennon Engleman.

Following the murder of Ronald Gusewelle, authorities were starting to notice the trend of connected deaths to Dr. Engleman. His patients and community, however, only saw a generous man committed to helping his community and its citizens. Apparently, Dr. Engleman was not the greatest dentist, however. He often did a sloppy job of making casts for dentures and dental appliances, requiring the work to have to be redone by the dental lab several times. His business was struggling, however, and he soon found himself in debt with the dental lab owned by Sophie Barrera.

Sophie Barrera owned the South St Louis Dental Laboratory and had grown tired of waiting for Dr. Engleman to pay up by 1980. She filed a lawsuit against the doctor that was set to go to court just a few days after Sophie was murdered. On January 14th, 1980, Sophie entered her vehicle in South St. Louis. Shortly after, the vehicle exploded. Police found remnants of a bomb under her charred vehicle. Sophie had told her son before she was in fear of being killed. She believed Dr. Glen Engleman was dangerous.

Dr. Engleman was questioned for three hours and then released. Police were certain he was responsible for Sophie’s death, but they had to prove it. The public also wondered if the bombing was related to other bombing in the area that were carried out between two mob families fighting for control over St. Louis’s labor unions. The evidence indicated however, that this was not a mob hit. The number one suspect was the man who owed Sophie $15,000. Dr. Engleman had to be stopped, but police weren’t sure how to do it.

Detectives soon began having conversations with Dr. Engleman’s ex-wife and mother of his son, Ruth. Ruth told police nothing at first, but eventually started to talk. She explained that Dr. Engleman often bragged about killing people. He told her that he had a superpower: he was able to kill without remorse. He had admitted to killing Eric Frey, Peter Halm, and the Gusewelle family. It was his side hustle… killing for profit.

Ruth agreed to help police, but none of her testimony could be used in court because Dr. Engleman confessed to her while the two were still married. He was protected by spousal privilege. Ruth decided to wear a wire, however, and met up with Dr. Engleman to exchange their son and sometimes just to socialize. They were still having a sexual relationship despite Dr. Engleman’s marriage to Carmen. She tried to get Dr. Engleman to confess to her again by asking directing questions. He didn’t seem to take the bait at first, and Ruth feared he would kill her next.

Ruth suggested police plant a bug in her bedroom and she would invite the dentist over for sex. Dr. Engleman was suspicious, however, and did not say anything that could lead to his arrest. Ruth then met his at a diner wearing a wire, and this time he made a comment about being “homicidally intimate” with the widow of one of his victims. He admitted to the murders in great detail, providing just what police needed for an arrest. He explained that he found murder more sexually satisfying than sex. His ex-wife was given a new life in the witness protection program.

Carmen, who was no longer married to the dentist, and her brother Nick were brought in for questioning to collaborate the allegations against Dr. Engleman. As possible co-conspirators, they asked for and were granted immunity to testify against the dentist. Carmen told quite the story. She said she was working for the dentist when he suggested she find someone with good benefits to marry. He told her about Eric Frey, who he said he directed Sandy Frey to marry with all intentions of committing murder for the insurance proceeds. Soon after she was married, Carmen said Dr. Engleman told her where to go and made sure her husband was shot and killed. He staged it to look like a target shooting accident.

Glennon Engleman was finally arrested and charged with murder in 1980. Carmen testified at Dr. Engleman’s first trial, for which he was convicted of murdering Peter Halm and given 50 years in prison. The dentist then pled guilty to the murder of Sophie Barrera to avoid the death penalty. Serving a lift sentence for that murder in Missouri, Dr. Engleman was back in court by 1985 in Illinois.

In 1984, Robert Handy, a convict and acquaintance of Dr. Engleman, admitted to authorities that he had taken part in the murder conspiracy of the Gusewelle family. He implicated Dr. Engleman, who had bludgeoned Ronald Gusewelle and shot him, as well as Ronald’s widow, Barbara Boyle. Dr. Engleman was given three life sentences for the Gusewelle murders. He also was convicted of federal mail fraud and given a thirty-year federal sentence. He is believed to have killed at least twelve people, including conspiring with his first wife to kill her husband, James Bullock, in 1958. Edna Ruth was never charged in the case due to lack of evidence.

Barbara Boyle went on trial for the murder of her in-laws, Arthur and Vernita Gusewelle, and husband Ronald in 1985. The jury acquitted her of the murders of Arthur and Vernita but convicted her of conspiracy to commit murder in the death of Ronald Gusewelle. Barbara Boyle was sentenced to fifty years in prison in 1985. She was granted parole in 2009.

Dr. Engleman enjoyed his notoriety in Missouri, often comparing himself to legendary outlaw Jesse James. He is believed to have killed at least twelve people, but the actual number is unknown. Unlike other serial killers, Dr. Engleman was inspired, at least in part, by greed. He also seemed to revel in his ability to not feel remorse. Dr. Engleman died of diabetes related health issues in 1999 at age seventy-two. He was incarcerated in Jefferson City at the time.


The FBI Files (2002) Season 1 Episode 5

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