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Preheat the oven to 400 degrees F.
Toss the broccoli together with the oil and sprinkle generously with salt and pepper. Spread the broccoli in an evenly spaced single layer onto a baking sheet. Roast until the florets just begin to char and the stems have softened slightly, 15 to 20 minutes.
In the meantime, add the bacon to a small skillet over medium heat. Cook, stirring occasionally until the fat has rendered and the bacon is almost crispy, about 5 minutes. Add the onion to the skillet and cook until slightly softened, 2 to 3 minutes. Add the vinegar and sugar and stir until the sugar has dissolved, about 1 minute.
Add the roasted broccoli to a large bowl and pour the bacon dressing over the top along with the walnuts, tossing to coat. Serve warm or at room temperature.