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Seared Radicchio and Roasted Beets

['6 medium beets, scrubbed', '5 tablespoons extra-virgin olive oil, divided', 'Kosher salt', '2 small heads of radicchio, cut into large wedges through root end', '1 cup pomegranate juice', '2 tablespoons red wine vinegar', '1/2 cup pomegranate seeds', 'Flaky sea salt (for serving)']

Preheat oven to 450°F. 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.
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.
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.
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.

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