In a medium skillet, cook the bacon over medium heat until cooked through but not crisp, about 6 minutes; drain on paper towels.
Cook the brussels sprouts in the bacon fat until golden brown and tender, about 10 minutes; discard the fat. Season with salt and pepper and drizzle with the maple syrup. Serve each brussels sprout on a toothpick with a piece of bacon and a cheddar cube.
