Writers commented on men dressing as women and doing “women's work.” Some reports assumed the practice was involved with religious functions; others used a tone of moral censure and claimed that young boys were “bred for this purpose.” Still others commented that persons engaging in such behavior were “persons of consequence” among their peers.

The tribes mentioned were the Miami and the Illinois. It's not clear if the Illinois were the Illini group that included the Peoria, Moingwena, Kaskaskia and others joined by the Algonquian languages or were a separate people like the Sauk, Fox, Winnebago and others who moved through what is now the state of Illinois ahead of encroaching settlement.

There is considerable evidence to support the fact that cross-dressing women fought in early American wars. Deborah Sampson fought alongside men in the Revolutionary War. Like Dr. Mary Walker in the Civil War, she cross-dressed, but unlike Walker, she attempted to hide her sex. Walker, a surgeon, was awarded the Congressional Medal of Honor as its only woman recipient, but it was later revoked along with some 900 others that had not been awarded for “actual combat with an enemy.” She continued to wear male clothing after the war and agitated for a woman's right to dress as she chose. Decades after her death, her medal was restored under President Jimmy Carter, on appeal from women's liberation groups.

Other women concealed their sex and continued to pass as men in their civilian lives—even marrying and successfully passing in all ways until accident or death revealed their secrets.

Of the 150-or-so recorded instances of “passing women” from the Civil War, one made the headlines in Chicago papers after the turn of the century. Jennie Hodgers, an Irish immigrant, had served honorably as Albert D. J. Cashier. When Cashier applied for a military pension, “he” was able to present a “bulging” file containing testimony from fellow comrades-in-arms. A 1910 accident eventually unmasked the former soldier's sex and led to the headline “A Woman in an Old Soldiers Home!” Hodgers/ Cashier, who served in an Illinois regiment, left behind a daguerreotype, which has been reprinted in several sources.

Another Chicago enlistee was Frank Miller (Frances Hook), who successfully masqueraded until wounded and captured by the Confederates. Hook's story was reported by the Chicago Tribune in 1909. And there is the case preserved for us by the historian Jonathan Ned Katz, of Nicholas de Raylan, who served as secretary to the Russian consul in Chicago. Twice married, he served as a soldier during the Spanish- American War, and was divorced by his first wife of 10 years for “misconduct with chorus girls.” His untimely death at 33 in 1906 revealed Nicholas to be a woman. In a will, “Nicholas” had made elaborate provisions to prevent detection. Neither wife would believe the truth, insisting “Nicholas” was a man. The reports say de Raylan wore “a very elaborately constructed artificial penis.”

Copyright 2008 by Marie J. Kuda

From Out and Proud in Chicago: An Overview of the City's Gay Community, edited by Tracy Baim, Surrey Books, 2008.