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Big Beans and Tomato Vinaigrette

['Handful of oregano sprigs', 'Handful of thyme sprigs', '2 bay leaves', '8 oz. dried butter beans, rinsed, soaked overnight if possible', '1 medium onion, halved', '1 large carrot, scrubbed, coarsely chopped', 'Kosher salt', '1/4 cup extra-virgin olive oil', '10 oz. cherry tomatoes or 1 1/2 cups chopped heirloom or beefsteak tomatoes', '1 garlic clove, smashed', '3 Tbsp. red wine vinegar', '1/3 cup extra-virgin olive oil, plus more for drizzling', 'Kosher salt', '2 lb. assorted heirloom, beefsteak and/or cherry tomatoes', 'Freshly ground black pepper', 'Handful of basil leaves', 'Mild red pepper flakes (such as Aleppo-style or Maras)']

Tie together oregano, thyme, and bay leaves with kitchen twine. Combine beans, onion, carrot, and herbs in a medium pot. Pour in water to cover beans by about 4" and bring to a very gentle simmer over medium-high heat. Immediately reduce heat and cook at the barest of simmers, stirring hardly at all, until beans are creamy and tender at the center but not falling apart or mushy, about 1 1/2 hours (this could take longer, depending on the beans). The key is to not agitate, which will help the beans maintain their shape. Remove pot from heat; season beans aggressively with salt. Gently stir in oil. Let cool. Drain beans; discard onion, carrot, and herbs.
Do Ahead: Beans can be made 2 days ahead. Keep in liquid; cover and chill.
Purée cherry tomatoes in a blender. Transfer to a small bowl and stir in garlic, vinegar, and 1/3 cup oil; season with salt. Let sit 15–20 minutes, then pluck out garlic.
Transfer drained beans to a medium bowl and add vinaigrette; toss gently to coat. Taste and add more salt if needed.
Slice, halve, or quarter heirloom tomatoes and arrange on a platter or divide among individual plates. Season with salt and pepper and drizzle with oil. Spoon beans along with plenty of vinaigrette over; top with basil and a few pinches of red pepper flakes.

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