heat broiler with a rack 6 inches from heating element and another rack below. Season pork with salt and pepper. Wrap bacon around pork in a single layer, stretching slices so ends overlap on bottom. Transfer to a rimmed baking sheet, seam side down. Lightly drizzle oil all over sheet around pork. Add polenta to sheet in a single layer, turn to coat with oil. Season with salt and pepper. Broil 5 minutes. Flip pork; broil 5 minutes more.
Meanwhile place asparagus on another rimmed baking sheet drizzle with oil and season with salt and pepper.
Reduce oven to 375. Flip pork Sean side down again. Place sheet with asparagus on lower rack. Roast until asparagus is crisp-tender and 140 degrees, about 12 minutes. Generously drizzle asparagus with vinegar. Let pork rest 10 minutes before carving and serving.
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