Glennon E. Engleman practiced dentistry in south St. Louis for years before anyone proved he had killed for money. When a car bomb killed Sophie Marie Barrera, the owner of a dental laboratory who was suing him over an unpaid bill, in January 1980, his former wife went to federal agents. The conversations she then recorded with him, at their home and in a restaurant, became the core of a federal case and two Missouri capital murder prosecutions. Juries convicted him of killing Peter J. Halm Jr., shot in 1976 so that Halm's wife could collect life insurance, and of killing Barrera. In 1985 he pleaded guilty in Illinois to killing a farm couple near Edwardsville and their son.
The courts that heard his cases described a method. Engleman, a slight, balding man, drew younger women into plans in which they married, insured the husband and shared the money after he killed him. One of those women testified under immunity that he had told her the plan would work because he had done it before, with a man named Eric Frey in 1963. Frey's death was never charged. Neither was the 1958 shooting of James Bullock, whose wife had earlier been married to Engleman; a federal civil court in 1961 found that the suspicions against Engleman in that case were not proof.
Engleman was serving two life terms in Missouri when he admitted the Illinois killings. He died in a Missouri prison in 1999, at 71, according to an Associated Press report published in 2009.
A 1961 federal court opinion describes him as a dentist employed at the time by the same company that employed James Bullock. He practiced in south St. Louis, and he owned a drag strip near Pacific, Missouri, with a partner. United Press International described him in 1984, when he was 57, as slight and balding.
To the investigators and prosecutors who dealt with him he was intelligent and controlling. Investigators told UPI in 1984 that he was "super intelligent," with an IQ in the 140s. Gordon Ankney, a prosecutor in his Missouri cases, compared him to a "Dr. Engleman and Mr. Hyde" and said he had a hypnotic hold over young women of the kind associated with Charles Manson. "He's as cold-blooded a murderer as I've ever seen," Ankney said. Fred Buckles, an assistant U.S. attorney, told UPI that Engleman's "hold on women" had nothing to do with his looks. Ankney also had a low opinion of his professional work and called him "a lousy dentist."
Engleman married more than once. The 1961 court opinion records that the woman James Bullock married in June 1958 was Engleman's former wife. His third wife was the one who went to the authorities in 1980; the court opinions call her his former wife by that time. The couple had a son, who was present at one of the recorded restaurant conversations in January 1980, according to the Missouri Supreme Court.
James Stanley Bullock was shot to death in St. Louis on December 17, 1958. He had married on June 28 of that year; his wife had earlier been married to Engleman. His death was never solved. In 1984 UPI reported that the case remained open, since murder has no statute of limitations.
The fullest account in a court record comes from a civil case over his life insurance, General American Life Insurance Co. v. Cole, decided in the federal district court in St. Louis on May 31, 1961. Three insurers held policies on Bullock's life: group and individual policies from General American, a policy from the Aid Association for Lutherans, and a Prudential policy with an accidental death benefit. Soon after the marriage the beneficiary on two of them had been changed from an aunt to his new wife. The insurers paid the money into court and asked the judge to decide who should receive it.
Two claimants challenged the widow. The aunt said the marriage had been a fraud designed to collect the insurance. The St. Louis County public administrator, acting for Bullock's estate, went further and alleged that the widow had conspired in his death. He named Engleman, her former husband, along with three other people. The court rejected both claims and ruled that the widow, as the named beneficiary, was entitled to the money. The judge found that the evidence against Engleman amounted to suspicion and inference, rejected the testimony of the two main witnesses offered against him, and noted that nothing placed him at the scene. The opinion said in plain terms that the court was not deciding who had killed Bullock, which remained officially unsolved.
UPI reported in 1984 that Bullock's widow had received $64,500 in life insurance and had invested $15,000 in Engleman's drag strip. Engleman was never charged with Bullock's death.
Eric Frey worked at the drag strip near Pacific. On September 23, 1963, he was killed in a dynamite explosion while he, Engleman and others were working in a well on the property. His death was not charged at the time.
The account of what happened came out years later, in Engleman's federal trial over the Halm killing. Engleman's partner in the drag strip testified that he and Engleman had each set off dynamite in the well that day while they worked with Frey and others, and that Frey was killed shortly afterward. The partner testified that Engleman later admitted killing Frey for the insurance money. The federal appeals court quoted his account of Engleman's words: "I killed him ... for the insurance." Representatives of insurance companies testified that Frey's widow had collected on policies after his death. UPI reported in 1984 that she received $37,000 and said she later gave Engleman $16,000 of it.
The Missouri Supreme Court, reviewing the state Halm trial, noted that the only evidence about Frey admitted there was Engleman's own statement to Halm's future wife that he had killed a man named Eric Frey for insurance money. The court held that the statement was admissible to show a common scheme or plan. No charge was ever filed over Frey's death, and the courts did not try it as a separate crime.
The woman at the center of the Halm case had worked for Engleman as a dental assistant trainee. The federal appeals court described her as much younger than he was and said she had known him for much of her life. When she came to him with money troubles, he suggested that she marry someone, take out insurance on him and let Engleman kill him, after which they would split the proceeds. He told her it would work because he had done it before, in 1963, with Eric Frey.
She agreed. At his suggestion she changed jobs, and he kept advising her. On October 31, 1975, she married Peter J. Halm Jr. After the wedding Engleman told her how to obtain insurance on her husband, how to put property in her name, and how to make herself the beneficiary on policies Halm already held.
Twice she brought her husband to places Engleman had chosen, and twice the planned shooting was called off. Robert Handy was present on one of those occasions; he had bought the rifle that was to be used. A third place near Pacific was then chosen, and the plan was rehearsed there.
On September 5, 1976, Peter Halm's wife brought him to a place near Pacific, where Engleman shot him with the rifle Handy had bought, according to the federal appeals court. Halm was dead on arrival at a hospital in Washington, Missouri.
Halm's widow later collected about $75,000 in insurance proceeds, the federal court found. The Missouri Supreme Court described one insurance check of $15,816.50, which her brother deposited. In March 1977 the brother took $10,000 in $100 bills and paid it to Engleman in cash. Engleman then met Handy, who suggested breaking the money into smaller bills so it could not be traced. Engleman's former wife testified in the state trial that he later gave her $10,000 in $100 bills, which she turned into a certificate of deposit. UPI reported the widow's account that she gave Engleman $10,000 of a $60,000 settlement.
Peter Halm's widow and her brother later testified against Engleman under grants of immunity.
In November 1977 Arthur Gusewelle, 61, and his wife, Vernita, 55, were killed at their farm near Edwardsville, Illinois. Their son Ronald was married to Barbara Gusewelle, later Barbara Boyle, a friend of Engleman's. Prosecutors in Illinois later alleged that she and Engleman had planned for her to marry a wealthy man and kill him for his inheritance and life insurance, and that they expected to share about $500,000.
Ronald Gusewelle, 33, was killed in March 1979. He was found dead four days later in East St. Louis, Illinois, the Associated Press reported in 2009. He had inherited an estate of about $340,000, and his wife held about $120,000 in insurance on his life, UPI reported in 1984.
Don Weber, the prosecutor in the Illinois case, later recalled that at the funeral she set a can of Pepsi on her husband's casket.
Sophie Marie Barrera owned a dental laboratory in St. Louis that did work for Engleman. By March 1978 he owed the laboratory $14,504.37, and it stopped doing his work. She sued him to collect. On March 9, 1979, the court entered a default inquiry against him, and on March 19 he moved to set it aside. Engleman was angry about the suit and made threats against her in conversations with his former wife, the Missouri Supreme Court found.
On March 20, 1979, a partially detonated dynamite bomb was found where Barrera kept her delivery vehicle. The dynamite was wet, and it caused only a small explosion. The next day Engleman told his former wife that he was responsible for it. He said an acquaintance had done it for him, that the bomb had gone off too soon and that the acquaintance had been hurt.
Barrera told her lawyer the same day that she would rather settle. No settlement was reached, but she did not press the default judgment, and the civil case was set for trial in the week of January 21, 1980.
At about 5 p.m. on January 14, 1980, a bomb exploded in her delivery vehicle in St. Louis and killed her. Investigators recovered pieces of a pressure switch similar in design to the one in the earlier device. The next evening, Engleman told his former wife that a television report about three men in orange uniforms seen near the vehicle was correct, according to the federal appeals court. UPI reported in 1984 that authorities believed Engleman built the bomb and that a second man placed it, and that the second man had not been tried for lack of evidence.
On January 16, 1980, Engleman's former wife contacted federal law enforcement about his past. UPI reported that she feared for her life. She agreed to help the Bureau of Alcohol, Tobacco and Firearms, and over the next weeks agents recorded her conversations with him in two ways.
On January 20 and January 26, 1980, she wore a transmitter. Some of those conversations took place at her home and some at a restaurant, where their son was present on January 26. On January 29, with her consent, agents put a recorder that did not transmit inside her home. It captured about four hours of conversation on January 29 and 30, and a further recording was made on January 31. On February 14, 1980, at the bureau's request, she again wore recording equipment while she talked with him.
On the tapes Engleman acknowledged his part with Halm's widow in a scheme to get money and said he had received $10,000 from her brother. In the conversations about Barrera he admitted that he had gained financially from her death, said she "deserved killing," and admitted his skill with explosive devices, the federal appeals court found. UPI quoted one line from the recordings: "Money, money, money, money."
A federal grand jury returned a 17-count indictment. The first count charged Engleman alone with damaging, by means of an explosive, a vehicle used in interstate commerce, causing Barrera's death. The other 16 counts charged Engleman and Robert Handy with conspiracy and mail fraud in the scheme to collect insurance on Peter Halm's life. Missouri charged Engleman with capital murder in both deaths.
Both men asked to move the federal trial out of St. Louis. On March 14, 1980, U.S. District Judge William L. Hungate agreed. He found that the case had received saturation coverage in the St. Louis media and that the spread of inflammatory publicity had created an atmosphere of widespread public prejudice. Among the headlines filed with the motion was "Dentist Is Suspect In Other Killings." The judge noted that the related state and federal proceedings had already been moved, and he ordered the case transferred to the District of Minnesota, on condition that each defendant consent in writing. The trial had been set for May 6, 1980.
In the Halm case a jury convicted Engleman and Handy on all 15 mail fraud counts and the conspiracy count. Engleman received an aggregate term of 30 years, and Handy received 20 years. In a separate trial a jury convicted Engleman on the explosives count over Barrera's death, and he received another 30 years, to run after the first sentence.
The prosecution in the Halm case put the Frey death before the jury through the drag-strip partner's testimony, and in the Barrera case it presented the failed bomb of March 1979. Engleman argued on appeal that neither should have been admitted, and he also challenged the recordings. On May 6, 1981, a three-judge panel of the U.S. Court of Appeals for the Eighth Circuit, in an opinion by Judge Roy L. Stephenson joined by Chief Judge Donald P. Lay and Judge Richard S. Arnold, affirmed both of Engleman's convictions. It held that the Frey evidence was properly admitted, that the earlier bomb was relevant to motive, intent, identity and a common plan, and that the recordings were properly used.
Handy's result was different. The court found that the trial judge should have given him a separate trial, because the Frey evidence was highly prejudicial to him and he had been "in no way involved" in that scheme. It also held that one of Engleman's recorded statements, about giving part of the money to Handy and Handy's wife, was not admissible against Handy because it had been made after the conspiracy was over. The court reversed Handy's conviction and sent his case back for a new trial. Rehearing was denied on June 3, 1981.
While that appeal was pending, Engleman filed a civil suit in April 1981 against his former wife, an ATF special agent, other agents, a St. Louis County police sergeant and the county police department. He claimed they had conspired to record his conversations in violation of his constitutional rights. The district court ruled that he had already litigated the recordings in his criminal case, and on November 10, 1981, the Eighth Circuit dismissed his appeal as frivolous.
The state charged Engleman with capital murder in the City of St. Louis, and the trial was moved to Gasconade County, Missouri. A first trial began in November 1980. A jury was chosen, kept together and heard five witnesses, but on the morning of November 13, 1980, the judge declared a mistrial at Engleman's request after the sheriff failed to keep the jurors together overnight.
The case was tried again in January 1981, and the jury found Engleman guilty of capital murder. He was sentenced to life imprisonment without eligibility for probation or parole until he had served at least 50 years. UPI reported in 1984 that he escaped a death sentence in the Barrera case because the jury could not agree on punishment.
On appeal Engleman argued that the second trial violated double jeopardy, that two jurors should have been excused, that the judge had made a prejudicial remark about the case's fame, that photographs and recordings should have been kept out, and that he should have had an alibi instruction. The Missouri Supreme Court rejected every claim. It held that the recordings, made with his wife's consent, did not violate the Fourth Amendment or the Missouri Constitution, since a person who confides in someone takes the risk that the confidant will record the conversation. It found that replaying one inaudible tape had been an error but not one that denied him a fair trial. Because the bomb went off when the vehicle was started and moved, the court said, his whereabouts at the time of death did not decide the case, and no alibi instruction was needed. The court affirmed the judgment on June 14, 1982, in an opinion by Special Judge John E. Parrish, and denied rehearing on July 6, 1982.
Engleman was also convicted in state court of the capital murder of Peter J. Halm Jr. and sentenced to life imprisonment without eligibility for parole for at least 50 years. Halm's widow and her brother testified under immunity. UPI reported that Engleman could not be sentenced to death for Halm's killing because Missouri had no death penalty at the time of that crime.
On appeal he argued that the evidence of the Frey killing should not have been admitted, that the tapes had been unlawfully seized, that the transcripts used with the tapes broke the best evidence rule and gave them undue weight, and that the jury should have been given a special warning about immunized witnesses. The Missouri Supreme Court rejected each point. The trial judge had found the tape "almost impossible to follow" without a transcript, but the agent who made the recording had authenticated the transcript, Engleman had admitted it was accurate, the jurors were told that the tape was the evidence, and the transcripts were collected after the tape was played. The standard instruction on witness credibility, the court held, was enough. The conviction was affirmed on June 30, 1983, in an opinion by Special Judge William E. Seay.
By 1984 Engleman was serving his two life terms, with no parole for 50 years, at the state penitentiary in Jefferson City, UPI reported. His health was poor. His sister told UPI that he had diabetes, had lost about 75 pounds and a toe, and had a hole in his neck, and that his health might keep him from standing trial in Illinois.
He talked to reporters. "Let's face it ... I'm a celebrity," he told one, and he claimed that a hit man had asked his advice. A police reporter told UPI that Engleman talked about parapsychology and was cocky. Engleman described himself in one statement quoted by UPI: "There's no possession on my part, no driving urgency to keep getting rid of my fellow man." His sister said he had asked to practice dentistry in prison, but officials feared lawsuits, and Ankney said the warden stopped the idea.
In August 1984 a grand jury in Madison County, Illinois, returned an indictment that named Engleman as the gunman in the killings of Ronald Gusewelle and his parents, UPI reported. The defendant charged was Ronald's widow, by then Barbara Boyle. She was arrested in Florida, where she had a packed car and a passport, and authorities said she may have been trying to reach Switzerland. Engleman and Handy were named as unindicted co-conspirators in her case.
Handy gave investigators an account of how Engleman had killed Ronald Gusewelle. Don Weber, the prosecutor, said he would seek the death penalty against Boyle.
Engleman admitted killing Ronald Gusewelle in 1979 and his parents two years earlier at their farm near Edwardsville. In 1985 he pleaded guilty to all three killings and received three concurrent life sentences, the Associated Press reported. Handy admitted helping to plan the killings, pleaded guilty to conspiracy and was sentenced to 14 years.
Boyle went to trial on three counts of murder. A jury found her guilty of her husband's murder and not guilty of the murders of his parents. She was sentenced to 50 years. She maintained that she had not helped Engleman kill her husband for the insurance money, and a request for clemency in 2002 was denied. She was released from the Dwight Correctional Center in October 2009, at 67, with her sentence cut short, and was placed under parole supervision in northern Illinois.
Weber said then that he was disappointed she had not received a life sentence or the death penalty. "The condition of her soul is between her and God," he said. "But between her and the judicial system, she has not paid her debt."
Engleman died in a Missouri prison in 1999, at 71, while serving the two life sentences for the Missouri murders, the Associated Press reported in 2009.
The case was the subject of a book, Appointment for Murder, an episode of the television series The FBI Files titled "Deadly Dentist," and a 1993 film, Beyond Suspicion, the Associated Press reported in 2009.
The deaths of James Bullock in 1958 and Eric Frey in 1963 were never charged against Engleman or anyone else. In Bullock's case, the only judicial finding is the 1961 civil ruling, which held that the evidence offered against Engleman and Bullock's widow was suspicion and inference and did not prove a conspiracy; the court left the killing unsolved. In Frey's case, two courts admitted evidence that Engleman said he had killed Frey for insurance money: the drag-strip partner's testimony in the federal trial and the testimony of Halm's widow in the state trial. Those statements were admitted to show a plan; neither trial decided whether he killed Frey. Frey's death is attributed to him only through those statements.
The amount of insurance in the Halm case varies by source. The federal appeals court found that Halm's widow collected about $75,000; the Missouri Supreme Court described a check of $15,816.50; UPI reported her account of a $60,000 settlement. All three sources agree that $10,000 in cash went to Engleman.
The man UPI said placed the bomb that killed Sophie Marie Barrera was never tried, according to that 1984 report. Engleman said an acquaintance set the first bomb; the courts did not name him.
December 17, 1958: James Stanley Bullock, whose wife had earlier been married to Engleman, is shot to death in St. Louis. The case is never solved.
May 31, 1961: a federal judge in St. Louis rules that Bullock's widow is entitled to his life insurance and finds no proof of a conspiracy involving Engleman.
September 23, 1963: Eric Frey is killed in a dynamite explosion at the drag strip near Pacific, Missouri. No charge is filed.
October 31, 1975: Engleman's former dental assistant trainee marries Peter J. Halm Jr.
September 5, 1976: Peter Halm is shot near Pacific and dies.
March 1977: the brother of Halm's widow pays Engleman $10,000 in cash.
November 1977: Arthur and Vernita Gusewelle are killed at their farm near Edwardsville, Illinois.
March 1978: Engleman owes Sophie Marie Barrera's laboratory $14,504.37; she later sues him.
March 1979: Ronald Gusewelle is killed; his body is found in East St. Louis.
March 9, 1979: a default inquiry is entered against Engleman in Barrera's suit.
March 20, 1979: a partly detonated bomb is found where Barrera keeps her delivery vehicle.
January 14, 1980: Barrera is killed by a bomb in her vehicle in St. Louis.
January 16, 1980: Engleman's former wife contacts federal law enforcement.
January 20 to February 14, 1980: she records conversations with Engleman for the ATF.
March 14, 1980: Judge Hungate orders the federal case moved to the District of Minnesota.
1980: federal juries convict Engleman of mail fraud, conspiracy and the explosives offense; 30 years on each case, consecutive.
November 13, 1980: a mistrial ends the first state trial in the Barrera case in Gasconade County.
January 1981: a Gasconade County jury convicts Engleman of the capital murder of Barrera; life without parole for 50 years.
April 1981: Engleman sues his former wife and the agents over the recordings.
May 6, 1981: the Eighth Circuit affirms Engleman's federal convictions and orders a new trial for Handy.
November 10, 1981: the Eighth Circuit dismisses Engleman's appeal in his civil suit as frivolous.
June 14, 1982: the Missouri Supreme Court affirms the Barrera conviction.
June 30, 1983: the Missouri Supreme Court affirms the Halm capital murder conviction.
August 1984: a Madison County, Illinois, indictment names Engleman as the gunman in the Gusewelle killings; Barbara Boyle is arrested in Florida.
1985: Engleman pleads guilty to the three Gusewelle killings and receives three concurrent life sentences.
1999: Engleman dies in a Missouri prison at 71.
October 2009: Barbara Boyle is released from the Dwight Correctional Center.