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Citrus-Pomegranate Relish

['1/2 cup sugar', '1/3 cup sherry vinegar', 'Kosher salt, freshly ground pepper', '4 small oranges (such as blood or Cara Cara) or tangelos', '1/2 cup pomegranate seeds']

Cook sugar undisturbed in a dry medium saucepan over medium-high until a ring around the edges is melted, about 5 minutes. Using a heatproof spatula, pull melted sugar in toward the center of saucepan. Continue to cook, pulling melted sugar into the center and reducing heat if sugar begins to smoke, until all sugar is melted and a deep caramel color, 6–8 minutes. Remove from heat and carefully add vinegar (it will spatter and caramel will seize). Cook sauce over medium heat, stirring, until caramel dissolves; season generously with salt and pepper. If sauce tastes too tart, add more salt a pinch at a time to balance out. Let cool.
Slice off ends from oranges; set on ends and remove skins and white pith. Slice oranges crosswise into 1/4"-thick rounds. Place in a large bowl; add pomegranate seeds and sauce and toss to coat.
Relish can be made 1 week ahead. Cover and chill. Let sit at room temperature 2 hours before serving.

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