Roasted Beets with Fennel and Bonito Dressing
['2 pounds small or medium red beets, scrubbed', '1/2 cup olive oil, divided', '2 teaspoons kosher salt, plus more', '1 teaspoon aniseed or fennel seeds', '1/2 cup white wine vinegar', '1 tablespoon sugar', '1 small fennel bulb, halved lengthwise, very thinly sliced crosswise', '2 garlic cloves, smashed', '2 tablespoons unsalted butter', '1/3 cup bonito flakes', '2 teaspoons fresh lemon juice', '1 cup trimmed mature arugula']
Preheat oven to 425°F. Toss beets with 1 Tbsp. oil in an 8x8" baking dish; season with salt. Add 1/4 cup water and cover tightly with foil. Roast beets, shaking once, until a knife slips easily through flesh, 60–75 minutes. Let cool slightly, then rub off skins with paper towels. Using 2 forks, tear beets into large pieces; toss in a large bowl with 2 Tbsp. oil.
Meanwhile, toast aniseed in a small saucepan over medium heat, tossing often until fragrant, about 3 minutes. Add vinegar, sugar, 2 tsp. salt, and 1 cup water. Increase heat to medium-high and bring to a simmer, stirring to dissolve sugar and salt, about 4 minutes. Remove from heat and let steep 20 minutes. Place fennel in a small bowl and strain brine over. Cover and chill until cold, about 2 hours.
Cook garlic, butter, and 1/4 cup oil in a small saucepan over medium, stirring occasionally, until garlic is soft but not brown, about 2 minutes. Stir in bonito flakes and transfer to a blender. Purée until only a few flecks of bonito remain.
Prepare a grill for medium heat. Grill beets, turning occasionally, until lightly charred, about 5 minutes. Transfer back to bowl; toss with bonito dressing and lemon juice and season with salt.
Toss arugula and remaining 1 Tbsp. oil in a medium bowl; season with salt. Grill until lightly charred in spots, about 30 seconds. Transfer back to bowl.
Arrange beets on a platter and top with arugula and drained pickled fennel.
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