Make 4 cuts into each potato without going all of the way through so that each potato has been cut into 5 thick slices. Place potatoes onto squares of aluminum foil. Sprinkle 1/4 teaspoon of salt inside each potato, then wrap with 3 slices of bacon and secure with toothpicks if needed. Brush the potatoes with olive oil, then sprinkle with brown sugar and black pepper. Wrap the potatoes loosely in the aluminum foil.
Grill potatoes until the bacon has crisped, and the potato is soft in the center, about 45 minutes depending on grill temperature.
