Preheat oven to 350°F. Line a standard muffin tin with paper liners.
In a small saucepan, stir together ½ cup granulated sugar and ½ cup water. Bring to a boil over medium high heat. Boil for 1 minute. Take off the heat and whisk in 1 tablespoon of instant espresso powder. Stir in the whiskey and let cool. Set aside.
In a large mixing bowl whisk together the flour, baking powder, salt, and remaining 1 tablespoon instant espresso powder.
Cream the butter and brown sugar together on medium high speed until fluffy (2 to 3 minutes). Add the eggs one at a time, mixing well and scraping the sides of the bowl after each addition. Turn the mixer to low and gradually add half the flour mixture, then the half-and-half and finally the rest of the flour mixture. Blend until almost all the flour is mixed in. Add the vanilla and mix. With a large spatula, finish mixing the batter.
Divide the batter evenly between the prepared muffin cups. Bake for 25 minutes or until a toothpick inserted in the center comes out clean. Let cool in the pan for 5 minutes and then spoon the coffee whiskey mixture evenly and slowly over the cupcakes. Let cool for 30 minutes in the pan then remove to a wire rack to finish cooling.
When the cupcakes are cool, whip the cream with the 2 teaspoons of sugar and swirl on top of the cupcakes.