The Gilded Age certainly saw some high-stakes wagers. Twelve years before Harry Bensley settled one bet by pushing a pram around the world, Annie “Londonderry” Kopchovsky settled another by circling the earth on a bicycle.

Annie’s task, proposed by two wealthy Boston clubmen, was to ride around the world in 15 months, earning $5,000 en route. She saw it as a challenge to make her way in a man’s world, and in 1895 the doughty 23-year-old, who had never ridden a bicycle before, pedaled out of Boston, leaving behind a husband and three children.

She brought only a change of clothes and a pearl-handled revolver, but she steadily earned money by carrying advertising banners and ribbons through cities around the world, starting with the Londonderry Lithia Spring Water Company, which paid her to carry its placard on her bike and to adopt her nickname.

That spirit carried her through. On returning home, the victorious Annie wrote a series of sensational features for the New York World, beginning with her cycling adventure. “I am a journalist and ‘a new woman,'” she wrote, “if that term means that I believe I can do anything that any man can do.”

The Chevalier d’Eon (1728-1810) lived the first half of his life as a man and the second as a woman. Until age 49 d’Eon served as a diplomat and soldier in Louis XV’s France, fighting in the Seven Years’ War and spying in London for the king.

But in 1771 he claimed he was physically a woman and asked to be recognized as such. The government agreed, even financing a new wardrobe, and the chevalier spent his remaining 33 years as a woman, participating in fencing tournaments and even offering to lead a division of women soldiers against the Habsburgs.

Doctors who examined him after death discovered that his body was anatomically male.