Pleasant Pruitt was born around 1840 in Edinburgh, Indiana, into an old but wealthy Protestant family. His upbringing gave him both social standing and respect in the small-town community. Those who knew him described him as intelligent and outwardly respectable, a man who carried himself with dignity and the appearance of moral uprightness.

As a young man, Pruitt married Miss Van Meter, a woman from Rushville, Indiana. Together, they had four children: Alice, Leslie, Ethel, and Clyde. To friends and neighbors, the Pruitts appeared to be an ordinary, stable, and happy family. Pleasant, known for his steady demeanor, was regarded as a trustworthy husband and father.

The first suspicious death occurred in 1888, when Pruitt's first wife—Miss Van Meter—died suddenly from what was believed to be poisoning. The small town of Edinburgh, Indiana, was shocked by the tragedy. However, no one suspected Pleasant. Known for his calm demeanor and reputation as a reliable, intelligent man, Pruitt remained above suspicion. No autopsy or investigation was conducted, and her death was ultimately dismissed as an unfortunate accident. The cause of death was never officially established, and Pruitt continued his life without any legal consequence.

Roughly one or two years after the death of his first wife, Pruitt remarried. His second wife was Naomi Huffman, and by all accounts, the couple appeared to be happy. That illusion shattered in 1896 when Naomi was shot and killed under extremely suspicious circumstances. Pruitt claimed the shooting was accidental—saying he had been cleaning and loading a shotgun in the back of the house when it discharged, fatally striking Naomi in the summer kitchen.

Neighbors, however, were not convinced. The memory of his first wife’s mysterious death resurfaced in the community's collective consciousness. For the first time, Pruitt faced formal suspicion. He was arrested and brought to trial. Despite community pressure, the jury found no clear motive. Testimonies described the couple as harmonious, and the prosecution lacked hard evidence. The result: Pruitt was acquitted. But the trial came at a cost. Legal fees and public suspicion drained him financially and socially. Pruitt quietly left town, hoping to escape the lingering shadows of two wives buried under unanswered questions.

Eventually, Pruitt relocated to Iowa City, where he met Winnie Berry, a widow with a teenage son named Jesse. The couple married and later moved to Indianapolis, Indiana, settling on East Ohio Street. As his financial situation worsened, Winnie suggested they convert their home into a boarding house. While the business brought some income, Pruitt grew increasingly reclusive and unstable. Tensions flared as he became irritated with how the house was managed. Quarrels with Winnie became routine, and boarders started moving out.

On the morning of October 9, 1902, Pruitt reached his breaking point.

After yet another argument, Winnie went down to the basement to wash clothes. Once her 14-year-old son Jesse had left for school, Pruitt followed her downstairs. In a violent outburst, he stabbed Winnie twice in the heart, striking her repeatedly in the face until her eyes were dislodged from their sockets. Her face was left disfigured beyond recognition.

Initially, it seemed Pruitt planned to flee. But instead of escaping, he returned to the basement with a loaded .38 caliber Bulldog revolver and shot himself in the head, collapsing dead on top of his wife’s mutilated body.

That afternoon, Jesse Berry returned home and called out for his mother. Getting no answer, he asked a boarder, Nicholas Yeager, who said Winnie had been in the basement all day doing laundry. Jesse descended into the dark basement, lighting a match to see—and was met with the horrifying sight of his stepfather's bloodied face. In shock, Jesse ran to the police station.

He encountered Officers Morgan and Simon, who followed him back to the house. Upon inspecting the cellar, Officer Morgan quickly recognized it as a murder-suicide scene. The officers broke the tragic news to Jesse gently, but the boy responded with heartbreaking calm: he had sensed it was coming and prayed that his mother and stepfather would find peace in Heaven.

A full investigation followed. Roomers were interviewed, and it became clear that the couple's escalating arguments were the likely motive. The brutality of the murder—paired with the emotional impact on a young boy—made headlines in Indiana and beyond.

In the weeks after the killings, a legal dispute broke out over ownership of the property. Frank McCray, administrator of Winnie’s estate, sued Otho C. George, representing Pruitt’s estate. The legal question was who held rightful claim to the couple’s shared assets. With Jesse being a minor, the case became further entangled in estate law. The final ruling of the lawsuit remains unclear.