Step 1

Heat a large frying pan over medium heat. Meanwhile, place 3 tablespoons of the olive oil, 2 tablespoons packed brown sugar, 1/2 teaspoon kosher salt, and 1/2 teaspoon black pepper in a large bowl and stir to combine. Trim and halve 1 pound Brussels sprouts. Add the sprouts to the bowl and toss to combine. Dice 3 thick-cut bacon slices.

Step 2

Add the bacon and remaining 2 tablespoons olive oil to the pan. Cook, stirring occasionally, until the bacon is golden brown and crisp, 5 to 7 minutes. Using a slotted spoon, transfer the bacon to a paper towel-lined plate.

Step 3

Add the Brussels sprouts to the pan and arrange cut-side down in a single layer. Cook undisturbed until the cut-sides are dark golden brown, about 4 minutes. Return the bacon to the pan and toss to combine. Cook, stirring occasionally, until the sprouts are crisp tender, 3 to 4 minutes more.