The starting point for this cocktail was the classic tropical drink the Mr. Bali Hai. That cocktail's combination of pineapple and coffee was so interesting and so unexpected It begged to be explored further. I decided to simplify it into an old fashioned style drink built in the glass. The pineapple bitters and lemon bitters do a lot of heavy lifting here, flavor wise. The pineapple bitters in particular marry well with the Mr. Black and provide the unique flavor combination that is the hallmark of the original cocktail. The Appleton 8 year gives you the big bold punch you expect from a Jamaican rum with enough vanilla and baking spice from the aging to play nice with the deep roasted flavors of Mr. Black. All the flavors a classic tropical drink in half the time!
Add the bitters, demerara syrup, Mr. Black, and rum to an old fashioned glass.
Add a big rock of tempered ice to the glass and stir until chilled and diluted.
Twist the lemon over the top and then put it on a pick with a chunk of pineapple.