Heat a large skillet over medium heat and add the chopped bacon. Cook until the pieces turn crispy and release their fat, about 6 to 8 minutes.
Remove the bacon with a slotted spoon and set it aside on a plate, leaving the rendered fat in the skillet.
Add the olive oil to the skillet if needed, then place the halved Brussels sprouts cut side down in a single layer. Sprinkle with salt and pepper. Let them cook undisturbed for 4 to 5 minutes so the bottoms brown.
Stir the sprouts and continue cooking for another 5 to 6 minutes until they soften but still hold their shape.
Return the cooked bacon to the skillet and pour in the maple syrup. Stir everything together and cook for 1 to 2 minutes more until the syrup thickens slightly and coats the ingredients evenly.
Remove from heat and transfer to a serving bowl.