It should surprise no one that Wild Bill Hickok was a ladies' man. As detailed in my book Wild Bill there were quite a few romances during his too-short life, some with local ladies referred to as “Indian Annies” in the towns he passed through. Some affairs, however, were more serious than others.
The first serious one that actually had James Butler Hickok—as he was known then—occurred when he was not yet 20 years old and new to Kansas, where he had moved from Illinois to establish a new family farms. Her name was Mary Jane Owen. Her parents were Patinux, a Shawnee Indian, and John Owen, who had taken a liking to the young newcomer. The older Owen would have been delighted to have the handsome James Hickok as a son-in-law, but it was not to be. Polly Hickok, the matriarch of the family, was appalled at the prospect of having grandchildren with Indian blood. In a letter to his family, signed James Hickok, he refers to Mary as “my gall,” and in another, signed James Butler Hickok: “I went to see my gall yesterday and eat 25 ears of Corn to fill up with. You ought to be here and eat some of hur buiskits. She is the only one I ever Saw that could beat mother making buiskits.” And in a letter dated August 23, 1858, he reports that Mary had cut off a lock of his hair and that he should send it to his mother and sisters.
How would she explain that to her neighbors in Illinois? And that her half-Indian daughter-in-law made better biscuits? Polly dispatches one of James’s brothers, Lorenzo, to Kansas to separate James from Mary Jane. Bidding a reluctant farewell to his former fiancé, James and his brother head west to new adventures.
One of those adventures involved spying behind enemy lines during the Civil War and Wild Bill finding his next love while doing it. When the war began, James Hickok, from an abolitionist family, joined the Union Army in the fight to free the slaves. At first, he was a scout and sharpshooter. Then, he became a spy, using disguises and Confederate clothing to infiltrate enemy lines and gather information.
The first major mission brought him into contact with Susannah Moore, another of his romantic partners. Hickok was a member of a party of men who had gathered information and ridden back roads looking for the Union line. They came upon a cabin in a clearing, and a black man working outside told them there were four guerrillas inside holding two women. Guns drawn, Hickok entered the cabin. The men inside must have been thoroughly surprised, hungover, or just unaccustomed to facing a man with pistols because Hickok was able to disarm all four. One of the two women was Moore, who “seemed much impressed by Hickok’s appearance and by his early mastery of the four guerillas,” according to one account.