In a large pot, cook mixture in 1 tbsp. olive oil until softened. Add 1 cup dry white wine, 1 cup water, 1 can (14 oz.) fire-roasted diced tomatoes, ¼ tsp. red chile flakes, and ½ tsp. each kosher salt and freshly ground black pepper. Cook, covered, for 10 minutes.
Add 2 cooked crabs (1½ lbs. each), cleaned, quartered, and cracked. Cook, covered, for 5 minutes. Transfer to a serving dish and sprinkle with chopped fresh oregano, flat-leaf parsley, and fennel fronds. Serve with warm, crusty bread.
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