Preheat the oven to 400°F. Line a rimmed baking sheet with foil and place a wire rack inside.
Working with one strip of bacon at a time, roll the bacon tightly to form a rosette. (Feel free to stack two strips prior to rolling for an even more robust-looking rose.) Secure the bacon rose with two toothpicks, forming a cross through the spiral as close to the bottom of one end as you can.
Space the bacon roses out on the wire rack. Brush bacon roses with maple syrup, then sprinkle with brown sugar and cracked black pepper.
Bake until the bacon is cooked through and crispy, 20 to 30 minutes. (If you double-layered the bacon, bake for 40 minutes.) Let cool slightly.
Carefully remove toothpicks, making sure the roses maintain their form. Place two basil leaves on a plate for each bacon rose, then place a bacon rose on top of each set of basil leaves.