Allen Roan and Tom Cooper killed a Union man in August 1861 that was part of the series of events that resulted in the Hildebrand family being targeted by the Federals.

A month later Tom Cooper and William Hildebrand, Sam's brother, were tried and convicted of treason.

And in the summer of 1869, in the biggest manhunt ever targeting Sam Hildebrand, law enforcement authorities arrested Sam's brother-in-law, William Harris, along with associates named Cash and Dunham, and tortured them to obtain information on the cave hideout of Sam. Harris was likely husband of one of Sam's sisters. After obtaining the information, the posse went to the cave, and shot it out with Sam. He escaped and promptly headed for the home of another sister, a Mrs. Adams.

So there we have Cooper, Cash and Adams--all names that connect into your family.

Based upon the basic genealogical sketch you have provided, here are my thoughts on the matter, for whatever they are worth.

Facts: The Roans, Coopers, Cashes, and Adamses were all inter-related through marriage. Fact: Sam's sister married into the Adams family (she is referred to as such by 1869 newspaper reports, as well as by Sam himself). Anyway, this extended family situation is is the classic definition of "shirttail relatives."

Theory: John Roan Sr. was referred to as an uncle, which may have been more of a title of respect as a patriarch of that particular extended clan. Sam himself may not have known how all of the pieces of the puzzle fit together, only that John was known as Uncle John. This is not unlike my own extended family on my maternal grandfather's side. From the 1870s through the 1890s they emigrated from Missouri to western Kansas, cleared out the Indians, built their soddies and raised their families. In this migration there were maybe nine or ten distinct families that were all inter-related in the same way as your family. My grandmother, who was 17 when she married my 30-year-old grandfather, came to know a large number of those Missouri emigrants who were getting up there in years as she met them. Family get-togethers were massive. In telling family stories toward the end of her life a few years back, my grandmother would refer to this man or that man as uncle this or uncle that. "I have no idea how they was all related, only that they said they was all related." In sorting out the genealogy, the people she referred to as uncles weren't uncles at all.

Anyway, your husband talking about being related to Sam Hildebrand isn't surprising--Sam said so in his autobiography. But, as theorized, perhaps Sam himself didn't even know exactly how it all fit together, only that maybe "Uncle John Roan" could put on a great feed with a hog on the spit on a Saturday night, crack open the white mule and fire up the fiddle and hoe down the row afterward, while his wife would cook up her famed possum and baked apple recipe for Sunday dinner as everybody was recovering from the night before. Anyway, according to my grandmother that's what Aunt Lyzie, Daddy Claggett, and Uncles Toot, Tat and Doc and the other Missouri transplants would do down on Medicine Creek back when she was a child bride in the first part of the 20th century.