Tagliata comes from the Italian word for “to cut,” referring to the fact that this steak is always served sliced. In fact, legend has it the dish originated with a particularly persnickety noblewoman who demanded that her servants do the carving for her. We’re honoring her request by carving up sirloin before serving and drizzling it with a balsamic sauce, which dribbles onto the sweet potato wedges, soaking them in tangy juices.
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Wash and dry all produce. Preheat oven to 450 degrees. Halve tomatoes lengthwise. Cut sweet potato into wedges. Strip rosemary from stems. Discard stems and roughly chop leaves until you have 1 tsp. Smash garlic with the back of a chef’s knife
Toss sweet potato on a baking sheet with garlic, chopped rosemary, a drizzle of olive oil, and a pinch of salt and pepper. Roast in oven until lightly browned and tender, about 20 minutes, flipping halfway through.
Meanwhile, in a small bowl, whisk together balsamic vinegar, 2 TBSP olive oil, and ½ tsp oregano (we sent more). Season with salt and pepper. Set aside.
Heat a drizzle of olive oil in a large pan over medium-high heat. Season steak all over with salt and pepper. Add to pan and cook until browned, 2-3 minutes per side. Transfer to a second baking sheet, then roast in oven until cooked to desired doneness, 5-7 minutes. Let rest 5 minutes after removing from oven.
While steak roasts, add vinaigrette and tomatoes to same pan used for steak. Allow to warm through using residual heat from pan.
Slice steak thinly against the grain. Divide arugula between plates and lay steak on top. Drizzle with tomatoes and vinaigrette. Serve with sweet potato wedges on the side.