Jessamine Flanagan is the widow of Commodore Doyle "Deadeye" Flanagan, mother of his five sons and Dinah, who is rumoured wildly to be the result of an affair with Prince Caine while Doyle was at sea for an extended amount of time.
She is a songstress, the beauty of her voice something spoken of often in Manzanil, and in her younger days she frequently performed at one bar or another, and even during ceremonies such as weddings and many a funeral. It's said that her voice is what lured Doyle to her, like a siren of lore, and got him to settle down enough to both take a wife, have children, and gain the ambition to become the Commodore of Manzanil.
While she is not the cruelest woman on the island, she is certainly one of the most well-respected, and that only partially has to do with whom her husband was and the children that are fiercely loyal to the woman. She runs a very tight network of spies, spreading throughout the five ports of Minos.
