There's nothing that compares to country ham, but prosciutto or ibérico would be the best options for subs—though I would love to have more people calling Nancy Newsom Mahaffey for the real deal. —George Weld
Cut the stems off of the figs and discard. Combine figs and all other ingredients in a saucepan, and stir well. Add water just to cover.
Bring pot to a simmer over medium heat, then lower heat and cook slowly, stirring regularly to prevent sticking. Add water as necessary to keep the jam from sticking or burning. Cook until figs have broken down somewhat (an hour or so). Purée gently with immersion blender or in a food processor, so that jam has a sticky but spreadable consistency.
For the biscuits and assembly:
Important note! Keep all ingredients for the biscuits cold throughout the process.
Heat the oven to 500° F. In a large bowl, combine the flours, baking powder, salt, and sugar and blend well.
Toss the 12 tablespoons of butter pieces into the flour and blend well with your fingers—you’ll squeeze and pinch the butter into the flour until it’s well-mixed and no piece of butter is larger than the fingernail on your smallest finger. The flour should resemble cornmeal. You want to do this step as quickly as possible so the butter does not begin to melt, but be thorough: getting the butter right is your best hedge against tough biscuits.
Add milk to the flour and butter. Working quickly, mix the milk in with a rubber spatula, mixing only until the dough begins to hold together.
Dump the dough onto floured work surface. Gather it together and pat briefly to flatten. Fold the dough over on itself 3 or 4 times, then pat into a rough rectangle about 3/4- to 1-inch thick. Use a bench scraper to ensure dough isn’t sticking to table.
Use 2 1/2-inch biscuit cutter to cut biscuits from dough. Do not twist cutter as you cut the biscuits. If the biscuits stick to the cutter, dip it in a little flour before cutting. Place the biscuits onto a well-buttered baking sheet. They should be almost touching. Brush tops lightly with buttermilk.
Bake for 15 to 20 minutes, until the biscuits are golden, well-risen and light; if they feel wet or heavy, bake them longer.
Lower the oven to 450° F. Split 4 of the biscuits (save the rest for another use!) and place on a baking sheet. Put a piece of the remaining 2 tablespoons butter on each side of each biscuit.
Next to the biscuits on the same baking sheet, divide the ham into 4 piles and cover with cheddar. Put the biscuits and ham into the oven and cook until the cheese and butter have melted.
To assemble, put a pile of cheese and ham on the bottom half of each biscuit. Add 2 teaspoons of fig jam to the top half, close, and serve.