Winnifred “Winnie” Jackson

Caught up in a social, economic, and justice system never meant for her, Winnie Jackson was victim to continued tragedy throughout her short life.

By Sean E. Andres

Winnifred “Winnie” Jackson was born in 1861 in Covington, Kentucky, to Andrew, a 35-year-old store worker who was referred to as “mulatto,” and Mary, a 30-year-old Black woman, both also born in Kentucky. Her father was literate and her mother was illiterate, while Winnie seems to have struggled in school, unable to write but could read at ten.

At 16, Winnie was arrested and charged for disorderly conduct and was fined $5. It was before or around this time that she no longer lived with her mother. In fact, her father seems to have died. This probably put financial strain on the widowed Mary and could have forced Winnie out of the house to work for her own living. It could have also been that Mary could not deal with Winnie’s brushes with the law.

Five months later, on 22 November 1877, Winnie attended a party at the Sherman household on 11th St., near the intersection with Scott Blvd. There, Winnie argued with the Sherman daughters – Kate, 18, and Maggie, 15 – over a boy named Pete Fry, described by the Enquirer as “a sable gallant.” About midnight, Maggie ran into the street. When she intended to return to the room with a rock, she met Winnie fleeing from Kate, who was pursuing her with a long knife. As Maggie was blocking Winnie’s path at the doorstep, Kate took the opportunity to catch up and stab Winnie in the right shoulder blade. Kate took three more shots at the screaming Winnie – cutting her ear, stabbing her left shoulder, and stabbing her in the neck under the chin. Witnesses said that Pete was hovering over them brandishing a revolver, but no one knew whom he intended to shoot. Somebody dragged Kate away, and she hid the bloody knife in a drawer inside. Her mother took it and attempted to hide it in her dress. When that failed to conceal the knife, she handed it to William Seton. 

Meanwhile, Winnie’s friends picked up her bleeding body to assist her to her home at Mr. John B. Landrum’s, 619 Scott Blvd. She told her friends she couldn’t walk anymore and that she wouldn’t make it, so they turned back and took her to the Shermans’ neighbor’s house to bed. They called on Dr. Temple, who said she’d not make it through the morning. She even gave her “dying statement” to the coroner. But she was still alive at 2 am when an Enquirer journalist visited her, and she vomited blood all night. The knife had punctured a lung. Officers McGraw and Bolan arrested Kate and Maggie and threw them in jail, charging them with cutting with intent to kill. They also arrested William Seton for possession of the weapon. Winnie held on, and four days later, Dr. Temple said she’d recover. 

The trial had taken over two months, and, ultimately, Kate was found guilty but without intent to kill and sentenced to 62.5 days in the county jail, or until she could pay the fine of $125. Apparently, she had come up with the money and was back in jail seven days later for a breach of peace. Three weeks later, Winnie was arrested and charged with being drunk and disorderly and fined $5. When John Landrum died nearly three months later, Winnie was forced to move, and she went to the other side of the Ohio to find opportunity in Cincinnati, where her mother also worked at the Emery Arcade for E. L. Dyer Hair Goods. She found employment as a chambermaid for Kate Dugan. But trouble followed her.

On 19 November 1878, Winnie cut someone in the head with a pen-knife and was sent to the workhouse for ten days. But her sentence would be stalled because she was to give testimony to the murder of Andy Colter. Not five months later, on 6 March 1879, Winnie, along with six other women residents physically fought in the streets of Bucktown and were arrested for disorderly conduct. Ultimately, she was fined $3 and costs. Later that month, she was again arrested, this time for grand larceny, but the case was dismissed. On 22 April, Winnie was arrested for disorderly conduct as a result of an altercation with her “old enemy” Kate and fined $13. 

1879 was not through with her yet. She ended up arrested yet again in November with Joshua Liverpool, a Black boy of 13. They were picked up for fighting on 6th St. between Main and Walnut. Winnie was sentenced to the workhouse for three months and Joshua to the House of Refuge until he came of age. When she returned from the workhouse, she moved into 54 George St. 

For three years, Winnie disappeared from the news. Not one report about run-ins with Kate. Not about her getting into fights. Not about her stealing. Until 31 December 1883, the day she died in Chicago from tuberculosis. She was 22.

Winnie’s short life isn’t meant to amuse, and it hurts to tell. It wasn’t uncommon to arrest and fine the lower class for the exact same thing the Cincinnati-, German-, and English-born citizens did on the regular. And how could you break out of a cycle meant to keep you in it, especially with no support system? The newspapers profited off exploiting the lower class, in particular the Irish and Black communities, writing about their arrests with amusement. Their sensationalized coverage of Winnie would always tie Kate Sherman into it as her archnemesis. It was entertainment for the established white residents of Cincinnati to see Black pain. I do hope Winnie experienced joy. I imagine her finding happiness in Chicago – for what little time she had there – away from prying eyes.

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