Patriotic Ladies in Drag

This Monday is Patriots' Day, which has been celebrated since 1969 in Massachusetts and Maine to commemorate the Battles of Lexington and Concord. I'm sure there will be a big crowd in those towns this weekend to watch the historical re-enactors do battle. It's a fun thing for tourists to do, and I'm sure the reenactors enjoy pretending to be someone else for a day. It's their day in the spotlight!

If we were able to travel back in time to the Revolutionary War, and if we looked closely, we'd see that some people in the American Continental army were also pretending to be something other than they really were.

I'm talking, of course, about women who disguised themselves as men to join the army.

I don't know how many there were across the thirteen colonies, but there were at least two cross-dressing patriots from New England. The first, Ann Bailey, was a Massachusetts native who enlisted in August of 1777. Ann served under Brigadier General John Patterson in the Boston Regiment under the name Samuel Gay. Her pseudonym seems very appropriate to a modern reader, but stop that giggling - gay didn't acquire it's current meaning until the 20th century.

Unfortunately, Ann's gay time in the army didn't last very long. Her femininity was discovered, and she was arrested. For attempting to serve the young nation she was sentenced to two months in jail and fined sixteen pounds plus court costs. (Interestingly, there is another more famous Anne Bailey from Virginia who wore men's clothing and joined the army.)

Deborah Sampson, 1760 - 1827

A different Massachusetts woman had a more successful military career. In 1782, Deborah Sampson joined the army under the name Robert Shurtleff. She fought admirably in several battles, and even treated her own wounds to avoid being discovered. Deborah eventually came down with a fever that she couldn't treat and was forced to seek help from a doctor. Surprisingly, he didn't reveal her secret and Deborah served until she was honorably discharged in 1787. Her true identity of course eventually came to light, but she still received pensions from the Commonwealth of Massachusetts and the United States, thanks to advocacy from Paul Revere.

What motivated these two ladies to cross-dress and join the army? Patriotism? Poverty? A need for adventure? And how do we fit them into modern categories like gay, straight, or transgendered?

Those are tough questions that I can't answer. Deborah Sampson did marry a man and have three children, but may have dallied with other women while she was disguised as a man. Herman Mann, the author of her 1797 biography, wrote the following:

To mention the intercourse of our Heroine with her sex, would, like others more dangerous, require an apology I know not how to make. It must be supposed, she acted more from necessity, than a voluntary impulse of passion.

I guess even then the official policy was don't ask, don't tell!

I got most of this information from the History Project's Improper Bostonians. Lesbian and Gay History from the Puritans to Playland. As always, the Web provides a wealth of information.