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Step 1
Preheat oven to 450°. Toss beets with 1 Tbsp. oil on a foil-lined rimmed baking sheet; season with kosher salt. Roast, tossing once, until skins are charred and beets are tender, 40–50 minutes. Let cool.
Step 2
Meanwhile, heat 2 Tbsp. oil in a large skillet over medium-high. Cook radicchio wedges on cut sides until browned, about 2 minutes per side. Transfer to a platter.
Step 3
Add pomegranate juice to skillet; bring to a boil and cook until thickened and syrupy, about 5 minutes. Stir in vinegar; season with kosher salt.
Step 4
Tear beets open and place around radicchio; spoon dressing over. Top salad with pomegranate seeds, sprinkle with sea salt, and drizzle with remaining 2 Tbsp. oil.