Preheat the grill to medium-high.
Drizzle each fig half with vinegar and fill each fig center with 1 tablespoon of the cheese. Sprinkle a couple flakes of crushed red pepper on top of the cheese and wrap each fig with a slice of prosciutto. Paint the outside of each fig very lightly with olive oil.
Put the figs on the grill. The idea here is that we want to grill the figs gently to cook the fig all the way through but to still get the char on the outside. Grill the figs on all sides so the prosciutto is starting to become crispy and the fig feels soft when squeezed, 5 to 6 minutes.
Drizzle a couple of drops of balsamic on each and serve. It's figgy delicious!