Kitty was born in the slums of London around 1652. Daughter of a harlot and unknown father(s), she graduated from petty crime in the streets to the stage of the Drury Lane theatre. She dreamt of catching the eye of some nobleman theatregoer and becoming a wealthy kept woman like her colleague Nell Gwyn, but her hopes were soon to be slashed when Gwyn had her framed and sentenced to transportation to America.

Her contract of indentured work was bought by Marmaduke Roydown, an ‘entrepreneur’ from Barbados. Kitty discovered there were no theatres in Bridgetown, and it wasn’t her services as an actress that Roydon was buying; instead he was running a brothel, a profitable business in the women-deprived colony. But Kitty was always a survivor, so she managed to convince one of her clients to buy her out, an old French merchant captain called Jérémie Chatelain. Chatelain paid half of the sizeable price for Kitty and promptly married her.

Madamme Chatelain spent her honeymoon aboard her husband's ship, the flute Alizé. She learned the rudiments of seamanship there, as well as the intricacies of commerce in the Caribbean. Chatelain’s first mate was Felipe Acero, a renegade Spaniard who insisted much more money could be made by smuggling and piracy, to which old Chatelain never wanted to commit. Felipe was also a dashing young man, and Kitty had never met a man she couldn’t seduce.

One dark night in late 1671, captain Chatelain fell overboard while drunk as a skunk. The (not extremely) dejected Kitty inherited the ship, which she renamed as Merry Widow.

After some risky investments and shrewd commercial operations, Kitty sold the Merry Widow and bought the galleon Sirensong at Port Goave.