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Bring a large pot of equal parts salted and sugared water to a boil. Once at a boil, add the rapini and blanch until bright green but still firm, 3 to 5 minutes. Add to an ice bath until cool, then allow to thoroughly dry on a kitchen towel-lined sheet tray.
Mix together the anchovies, finishing olive oil, red wine vinegar, basil, parsley, black olives and Fresno in a small bowl. Set aside.
Heat a 12-inch cast-iron skillet over medium-high heat and add the cooking olive oil. Once the oil is heated, add the rapini, in batches if needed, and allow to slightly char, about 3 minutes. Add the chopped garlic and stir to combine, allowing the garlic to soften and bloom, about 1 minute. Transfer to a platter. Drizzle with the anchovy vinaigrette.
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