Jolly Roger is (very) loosely based on the true adventures of 18th century gentleman pirate Stede Bonnet. After trading his seemingly wonderful life as a gentleman for the thrilling life of a pirate, Stede becomes captain of the pirate ship The Revenge. Stede struggles to earn the respect of his would-be mutinous crew, and after a fateful clash with the infamous Captain Blackbeard, his fortunes change. To their surprise, the very different Stede and Blackbeard find more than friendship on the high seas...they find love. Now, the two must survive it all.