The Southside Dentist: License to Drill, Contract to Kill

Dentophobia—the fear of going to the dentist. Studies indicate that as many as one in five people suffer from the malady. Because sufferers experience anything from slight anxiety to full-blown panic attacks, many forgo their dental care rather than visit their dentist. The phobia is irrational, as most are. After all, there’s nothing sinister about a doctor specially trained in the care of teeth, right?

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Many of the working-class residents on the south side of St. Louis weren’t afraid to visit their dentist. Their dentist was kind, generous, and most of all, he was one of them. Born and raised in their underprivileged neighborhood, he’d attended college at prestigious Washington University in St. Louis on the G.I. Bill. Following graduation, he began practicing dentistry next door to an adult bookstore in his old neighborhood rather than some fancy suburb office that his WashU degree could have accorded him. Their caring dentist hired only poor and uneducated locals to work in his office, and then took the time to train them as dental assistants and hygienists. Their dentist was so kind, in fact, that he wouldn’t charge those who couldn’t pay. Even more, he did charitable work in the community.

“I didn’t have a coat in high school,” a St. Louis man remembered years later. “He drove me to Sears and bought me one and then drove me to school.”

If there was anything about the dentist worthy of criticism, it was his sexual appetite. The dentist’s silver tongue had endowed him with powers equal to those of a Svengali, practically hypnotizing women into sexual relationships with him. He hired only young attractive women, catered to beautiful female patients, and often used his dental chair for more than the American Dental Association sanctioned. The dental Don Juan’s extracurricular activities ruined his three marriages. What’s more, because he continuously splurged on profuse affairs with employees, patients, and even ex-wives, he turned to a devilishly brutish skill that he secretly possessed to help make ends meet.

“I learned early in life that I possessed a special talent,” the dentist later boasted. “I can kill in cold blood without any remorse.”

Moonlighting as a hired assassin, the dentist discovered that killing husbands was his specialty. Not out of love or jealousy, but for money, usually a percentage of insurance proceeds on the husband’s life. The opportunistic dentist would even manufacture husbands by playing cupid, as he did for at least two women. Incredibly, the young women would willingly agree to stand at the altar fully aware that their husbands would soon be murdered by their dentist lover turned hitman. He also murdered the husband of a female patient and lover as well as her parents-in-law so that she could inherit the family’s wealth, in exchange for a large fee for him, of course.

The dentist typically staged the murders as accidents or home intrusions gone awry. He occasionally copied the execution-style murders perpetrated by warring factions of the St. Louis mob of the time. Guns, dynamite, and hammers—the choice of weapon varied widely. Strictly freelance, the killing dentist reveled in his careful planning. A fellow criminal recalled that the dentist “always planned his crimes from the witness stand backward.” He also rejoiced when his crimes went unsolved. “I like to kill,” he admitted later. “It sets a man apart from his fellow man if he can kill.”

But like all good things, all bad things too must end, and end they did in January 1980, his third decade of murders. The dentist planted a bomb in the car of a dental supplier who had sued him to collect nearly $15,000 in past-due bills ($50,000 today). Car bombs had been the St. Louis mob’s weapon of choice at the time and were frequently in the news. The dentist’s homemade bomb was effective—automobile fragments and body parts littered two city blocks—but he’d failed to select identical bomb components. Law enforcement quickly determined that the bomb was not the type used by local mobsters. Their investigation then focused on the dental supplier’s only known enemy and principal debtor—Glennon Engleman DDS.

Despite that the police had the dentist squarely in their sights, the jig wasn’t up, at least not yet. Dr. Engleman was not only intelligent, he was street smart. He knew that authorities had no real evidence, and he knew that no one dared to flip on him. “His voice would easily transition from a soft-spoken dentist to a killer who threatened those around him,” an ATF agent recollected. “They knew he’d killed before and he would kill them if they talked.”

With no one talking, law enforcement contrived an elaborate scheme whereby they offered the dentist’s third ex-wife protection within the U.S. Federal Witness Protection Program if she cooperated, which she agreed to do. The FBI bugged her home and telephones in the hope that she could elicit a confession from him. When that didn’t work, the ex-wife agreed to engage in sex with the dentist in a bugged bedroom. He gave the tape recorders nothing more than salacious pillow talk.

But the lawmen were patient and at last, the good dentist slipped while dining with his ex-wife, who was wearing a hidden microphone. She asked if he was still sexually intimate with a young dental assistant who’d once worked for him. He explained that no, they were “homicidally intimate,” having killed her husband, which was more arousing than sexual intimacy. With that confession on tape and the ex-wife’s cooperation, the dental assistant agreed to testify in exchange for immunity.

Dr. Engleman delighted in his Missouri notoriety. “I’m a celebrity—Jesse James, the Dalton Gang, and Dr. Engleman.” He eventually confessed to or was convicted of murdering five people. He was suspected of killing at least seven more, but there’d be no more confessions. Dr. Engleman died in prison in 1999.

For those who’d learned of the evil nature of their neighborhood dentist, his death once and for all eliminated their fear—not of going to see the dentist, but of the dentist coming to see them.