Put the bacon in a small skillet and cook over medium heat, stirring often, until brown and crisp, about 10 minutes. Stir in 1 tablespoon of the sugar. Cook, stirring, until dissolved, about 1 minute. Remove the bacon with a slotted spoon to a plate.
Whisk together the flour, cocoa powder, baking powder, baking soda, salt and remaining 1/3 cup sugar in a large bowl. Add the butter and use a pastry cutter or your fingers to cut the butter into the flour mixture until it resembles a coarse meal with some pea-sized lumps. Make a well in the center of the mixture, then gradually add the half-and-half, stirring to incorporate it into the mix.
Set aside about 2 tablespoons of the bacon. Knead the rest of the bacon into the dough a few times, then turn the dough out onto a lightly floured surface and pat it out to a 3/4-inch-thick circle. Cut out biscuits with a 2-inch round cutter, transferring them to an ungreased baking sheet. Gather the scraps, reshape and cut out more biscuits (discard any remaining scraps). Brush the biscuits with a little half and half and sprinkle each with a bit of the reserved bacon. Bake the biscuits until puffed and set, 10 to 12 minutes.
Meanwhile beat the cream and maple syrup together until it holds stiff peaks; beat in the whiskey. Serve the warm biscuits with the whipped cream.