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Black Barley, Fennel, and Radish Salad

['2 cups black or pearl barley, rinsed', 'Kosher salt', '1 large fennel bulb (about 10 ounces), 2 tablespoons fronds set aside, bulb cut lengthwise into 1/4" slices', '2 tablespoons plus 1/2 cup olive oil', 'Freshly ground black pepper', '1/3 cup fresh orange juice', '1/4 cup fresh lime juice', '1 small shallot, minced', '2 tablespoons chopped fresh dill plus 1/2 cup dill sprigs, divided', '1 teaspoon finely grated orange zest', '4 large radishes, thinly sliced, divided', '1/4 cup oil-cured olives', 'pitted', 'halved lengthwise']

Preheat oven to 425°F. Place barley in a medium pot and add water to cover by 1 1/2". Season with salt. Bring to a boil; reduce heat and simmer uncovered until barley is tender and water is absorbed, 40-45 minutes. Spread out barley on a large rimmed baking sheet; let cool.
While barley is cooking, toss fennel slices and 2 tablespoons oil in a medium bowl to coat. Season with salt and pepper. Spread fennel slices out in a single layer on another rimmed baking sheet. Roast until fennel is crisp-tender and beginning to brown in spots, about 18 minutes. Let fennel cool on baking sheet. DO AHEAD: Barley and fennel can be prepared 1 day ahead. Cover separately and refrigerate.
Whisk orange juice, lime juice, shallot, 2 tablespoons dill, and zest in a medium bowl. Gradually whisk in remaining 1/2 cup oil; season orange vinaigrette with salt and pepper.
Transfer barley to a large bowl; add roasted fennel, along with any accumulated juices on baking sheet. Add half of radishes, olives, and 1/4 cup dill sprigs. Drizzle 1/2 cup orange vinaigrette over and toss to coat; season with salt and pepper. Arrange salad on a large platter.
Scatter remaining radishes, reserved fennel fronds, and remaining 1/4 cup dill sprigs over salad. Pass remaining orange vinaigrette alongside for drizzling over.

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