Prep the Fruit: Place the chopped apples, orange wheels, and lemon wheels into the bottom of a large glass pitcher.
Macerate: Sprinkle the sugar over the fruit. Use a long wooden spoon to gently muddle the fruit for about 30 seconds to release the natural oils and juices.
Combine Liquids: Pour in the brandy, fresh orange juice, and the entire bottle of red wine. Drop in the cinnamon stick if using.
Stir & Chill: Stir the mixture thoroughly until the sugar completely dissolves. Cover the pitcher and refrigerate for at least 4 hours, preferably overnight.
Serve: Give it a good stir, pour over glasses filled generously with ice, and spoon some of the wine-soaked fruit into each glass.