Place the bacon in the freezer for 5 minutes to make it easier to handle. Meanwhile, rinse sprouts, trim off the ends, and halve them through the root end. Toss with the oil, salt, and pepper in a medium bowl.
Separate the bacon slices and cut them in half lengthwise with a sharp paring knife. Cut each strip in half crosswise, making 4 pieces. Starting with the cut side of a sprout, wrap a piece of bacon around the sprout.
Ideally, the bacon will wrap all the way around the sprout and end on the cut side. Depending on the size of the spouts, the bacon may wrap around 1 1/2 times, that’s fine.
Place the sprouts cut side down on the baking sheet, arranging them with 1/2 inch space between them. The sprouts can be covered in foil and stored in the refrigerator for up to 3 days. Let stand at room temperature while the oven is preheating.
Transfer the sprouts to the oven and bake on the center rack for 20 minutes. Remove the baking sheet from the oven and brush the sprouts lightly with maple syrup.
Return to the oven, increase heat to 425°F, and cook until the bottoms are deeply browned and the bacon is crispy, 8 to 10 minutes more.
Carefully transfer the sprouts to a small serving plate or bowl with a small spatula (I use an offset frosting spatula) and serve with cocktail forks or picks for picking up the hot sprouts.
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