Jack McConnell (1900 - ?) crane operator, driver, pugilist

In January 1922, in Philadelphia, a young man, Jack McConnell, was arrested after a fracas with his girlfriend. 

McConnell was a remarkable 22-year-old. His grandfather was James Gray, a retired member of the New York and Virginia bar, who had raised the child alone after the deaths of his daughter and then of his wife. They had travelled much across the mid-west, and from mid-teens, Jack had thrived in the more masculine trades. He had worked with machines, as a crane operator, and driven both four-horse teams, five-ton trucks and ambulances. 

He also joined juvenile gangs, usually after demonstrating his ability as a fighter. In Philadelphia it was the Iron Gang. He beat their best swimmers by swimming three and a half miles across the Delaware River, and became the leader of the gang. 

But the remarkable thing about young Jack was that when he was stripped and bathed after arrest, it was discovered that he had a female body. He admitted to another name: Florence Gray. 

The judge granted a suspension of sentence on parole but only on the condition that Jack live exclusively as Florence. She was supplied with a blouse, a skirt, silk stockings and the rest. Her major problem was finding work. Despite her driving experience, no one would employ a woman to drive. 

The transformation of Jack into Florence was kept quiet until August 1922 when the new leader of the Iron Gang entered a soda shop and recognized Jack. He made queer-phobic comments about Jack being in female clothing, a fight ensued but Florence fell over her skirts and came off worse. The man was arrested and sent up for a year. 

But the story was now out. Several newspapers - especially the Washington Times - ran the story in detail for a few weeks, and then, as newspapers do, they lost interest. Florence had spoken at length about getting into the girl-thing, dresses, heels, make-up and so on - as she was expected to do. 

It is not known what Jack/Florence did after the period of parole was up, and the newspapers were no longer paying attention.

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Men’s swimming togs in the 1920s included chest covering, which would not automatically have outed Jack.

Yes, silk stockings, not the cotton stocking that most women wore.

The Washington Times was published 1893-1939. The publication currently using the same title is a different publication.

Nowadays, in some jurisdiction Jack could be charged with rape for obtaining sexual services by deceit.  And in others James Gray could be charged with child abuse for allowing his grand-daughter to be a trans-boy.

There is currently (March 2022) a play being performed in Philadelphia that takes the basics of Jack's story, and adds extra.  

• “Fighting ‘Iron Gang’ Leader, Whipped, Turns Out to be a Girl”. The Evening World, August 9, 1922:8.
• Florence Gray. “Girl who led Iron Gang, posing as Boy, Seeks Movie Job: Now like Feminine Trinkets”. The Washington Times, August 12, 1922: 2.
• “’Truck Driver’ proves to be girl”. Calexio Chronicle, August 14, 1922.
• “Girl Pretender tells about her ‘Gang’ “. The Union Times, August 18, 1922.
• “Girl Adventurer lived for sixteen years as a boy; ‘Whistling Jack McConnell revealed as Florence Gray”. The Washington Times, September 3, 1922: 3,7.
• “How they found out Florence was a Girl”. The Washington Times, September 24, 1922: 7.
• Toby Zinman. “Florence becomes Jack - and famous”. Philadelphia Inquirer, March 7, 2022. Online.