True Tales of Murder and Mayhem

Boston's 25 most sensational, notorious, infamous, and sometimes just downright weird crimes of all time.

Edited by Chris Vogel and S.I. Rosenbaum

true crime boston hr

true crime boston

Photo via AP

Boston is a city of many facets. Not all of them sparkle. While our burg has a rep for high culture and higher learning, anyone can tell you it’s not all duck boats and sunshine around here. Boston has a seamy underbelly.

What is it about the city, for example, that produces such devious serial killers? Albert DeSalvo, a.k.a. the Boston Strangler, and his lesser-known predecessor, the murderous nurse Jane Toppan, both left a trail of bodies before anyone caught on to their dark compulsions.

Only Boston, with its casual corruption, could have nurtured a sociopath like Whitey Bulger, coddled by an FBI office that thought it was using him when, in fact, the opposite was true. Even as federal agents dismantled the Italian mob, they were doing Whitey’s dirty work.

And only a city as racially contorted and partitioned as Boston would have fallen for Charles Stuart’s nonexistent bogeyman, or provided Bush—the first Bush—with so potent a weapon as Willie Horton.

It’s not exactly that we love these monsters—but we’re proud of having survived them. And we never, ever shut up about them.

true crime boston number 1

The Poisonous Nursemaid

Morphine and atropine. Mixed up in a glass with a splash of mineral water. That was one of Jane Toppan’s favorite methods to snuff out the lives of dozens of people—patients, friends, coworkers, even her own foster sister—in the hospital wards and bedrooms of Victorian Massachusetts. Around the same time Jack the Ripper was disemboweling streetwalkers in Whitechapel and Lizzie Borden was allegedly hacking up her parents in Fall River, Toppan was carrying on a quieter rampage—eventually killing more people than both of them combined. In fact, Toppan was one of the most prolific serial killers in American history—at least on par with Ted Bundy and John Wayne Gacy in her death count. And yet, she is barely remembered today, perhaps because she killed her victims not at the point of a knife or the edge of an ax, but at the rim of a glass.

They called her “Jolly Jane.” A chubby Irish spinster with dark eyes and big rosy cheeks, she could always be counted on to liven up an occasion with jokes and family stories—like the one about her brother, the hero of Gettsyburg, or her beautiful sister who had married an English lord. Who cared if they were true? In fact, Jane—born Honora Kelley—had been raised in the Boston Female Asylum, an orphanage on Washington Street in the South End, after her violent and abusive father had abandoned her there.

At age six, she was contracted out as a domestic servant to the Toppan family, where she was informally adopted. While she seemed cheery enough on the outside, on the inside she seethed against her privileged foster sister, Elizabeth Brigham, who acquired the family fortune along with a marriage to an upstanding, if homely, deacon. Toppan, on the other hand, was jilted by a suitor who called off an engagement. After that, her resentment of Brigham turned to hatred.

In 1885, she began working as a nurse, training at Cambridge Hospital on Mount Auburn Street. Walking the wards at night, she began to conduct what she later called “scientific experiments” on patients. Her favorite tools were morphine—which causes pupils to contract and breathing to slow, eventually leading to coma—and atropine, a drug derived from the belladonna plant that has the opposite effect: An overdose dilates pupils and causes a giddy exuberance that ends in death by painful spasms.

Mixing the two drugs, Toppan alternately sank her victims into a stupor, and then roused them to heights of delirium, toying with them until she was ready to administer a final dose. All the while, she whipped herself into a sexual frenzy. One patient who barely survived the poisoning later described how Toppan climbed into bed with her and pressed against her, stroking her hair and caressing her through her bedclothes as she tried to give her a last sip of mineral water.

Toppan soon moved on to Mass General, where she continued her experiments on patients, and continued to get off on their death throes. After too many patients died in her care there, she was dismissed from the hospital by administrators who thought her careless with her dosages. Toppan simply moved on to an even better position from which to kill, starting work in 1891 as a private nurse to some of the most distinguished families of Cambridge and Boston.

At the same time, she began expanding her list of victims beyond her patients. She poisoned her landlords to avoid paying rent. She killed a friend in hopes of getting her job at a seminary. Finally, on a warm, sunny day in 1899, she walked with her foster sister, Elizabeth Brigham, down to the beach on Buzzards Bay for a picnic. Dressed in white frocks and sailor caps, the ladies snacked on cold corn beef and saltwater taffy. The next morning, Elizabeth was unable to get out of bed. Two days later, she was dead.

The doctor at the scene said the sudden death was from a “stroke of apoplexy.” Brigham’s distraught husband, Oramel, could only thank Toppan for caring so tenderly for his wife in her last moments. In her eventual confession, Toppan said her sister was “really the first of my victims that I actually hated and poisoned with vindictive purpose.”

After that, Toppan became even more brazen, wiping out the entire Davis family, owners of the cottage where she stayed in Buzzards Bay in 1901. First, she killed the mother of the family, Mattie, when she traveled up to Cambridge to confront Toppan for not paying her rent. Then, traveling down to Cataumet, Toppan offed the youngest daughter, Genevieve, spreading rumors that she’d killed herself with insecticide. The patriarch of the family, Alden, went next. Finally, Toppan poisoned the older sister, her friend Minnie. As the other woman lay dying in the house that night, Toppan held Minnie’s 10-year-old son in her arms.

Though Toppan had managed to get away with her murders for years, the coincidences around these deaths were too great to ignore. Toppan returned to Cambridge, where she poisoned Oramel’s sister in the hopes of getting him all to herself to marry. Meanwhile, authorities on Cape Cod were exhuming the Davis family’s bodies under suspicion that they had been poisoned. They arrested Toppan that fall, and tied her to the murder weapon when a local pharmacist told them he’d sold Toppan enough morphine to send into eternal rest “a score of persons.”

Toppan eventually confessed to her crimes—counting 31 people she knew she’d killed, along with at least a dozen more nameless victims in her nursing years. Estimates of the number of victims during her 15-year career range as high as a hundred. Newspapers blanketed their pages with stories of her crimes for months, putting her on par with Lucrezia Borgia and Catherine de Medici as one of the most ruthless women in history. The Boston Globe went farther, branding her the “greatest criminal in the country,” while the Boston Traveler called the crimes the “most horrible case of degeneracy [the] world has ever known.”

People from all around New England descended on the Barnstable County Courthouse for Toppan’s trial in June 1902. When the jury emerged from deliberations, they declared her not guilty by reason of insanity. Toppan remained completely unmoved. In her last confession, printed in the New York Journal, she boasted about fooling doctors for years, and regretted only that she tipped her hand by poisoning “four people in one family almost at once. That was the greatest mistake of my life.”

The only person for whom she consistently expressed sorrow was herself, blaming her crimes on the fiancé who jilted her decades before. After that, she wrote, “I still laughed and was jolly, but I learned how to hate, too. If I had been a married woman, I probably would not have killed all these people.” Toppan lived out the rest of her days in the Taunton Lunatic Asylum—becoming increasingly deranged and paranoid as the years went on. In letters to lawyers and doctors, she repeatedly accused hospital staff of trying to poison her.

—By Michael Blanding

true crime boston number 2

Doctor Death (1849)

It was a chilly day in November 1849 when George Parkman, a noted Harvard surgeon, entered the chemistry lab of his colleague John White Webster, never to be seen alive again. A janitor discovered the remains of Parkman’s dismembered body hidden in the walls of the lab a week later, prompting Webster’s arrest and spurring an international media frenzy the likes of which the city had never seen. The ensuing murder trial made history when the presiding judge, Chief Justice Lemuel Shaw, instructed the jury that the prosecution had to prove Webster’s guilt only “beyond a reasonable doubt,” a precedent now known as the “Webster Charge.” The subsequent conviction was the first based on this new guideline, as well as on testimony provided by medical experts. —Andrea Timpano

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The Killer Child (1874)

Some called him a fiend. Others called him a degenerate. Everyone called him a murderer. Jesse Pomeroy became the most famous—and youngest—sociopathic killer in America, confessing at the age of 14 to the grisly murders of two children. A troubled teen, Pomeroy was well known to local police at the time of his confession, having been arrested previously for using a knife to torture other kids in his South Boston neighborhood. Though he was sentenced to death for the murders, Pomeroy was never hanged. Instead he was incarcerated at the state prison in Charlestown for more than 50 years, serving much of that time in solitary confinement. —A.T.

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The Brinks Bank Job (1950)

It was almost the perfect crime. On the night of January 17, 11 masked men used stolen security plans to break into the Brinks armored-car depot in the North End. Thirty minutes, five tied-up employees, and 14 canvas bags later, they made off with more than $2 million in cash, checks, and money orders. They eluded capture for nearly six years before Joseph James O’Keefe, one of the gang, gave up his accomplices to the FBI—just days before the statute of limitations was to expire. To this day, the stolen money has yet to be recovered in full. —A.T.

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Murder by Mail (1912)

They called him the “Postcard Killer.” John Frank Hickey earned the moniker after sending anonymous messages to police detailing his crimes and the locations of his victims’ bodies. Detectives used the messages to trace Hickey, eventually apprehending him at a home for inebriates in New Jersey. The Lowell native copped to the murders of one man and two young boys, as well as assaults on numerous children, over a period of nearly 30 years. He claimed his violent acts were fueled by liquor-induced rage, and argued the insanity defense at his trial. The jury found Hickey guilty of second-degree murder. —A.T.