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Blacken tomatoes on a piping hot outdoor grill, chop and combine with red onions and basil oil to make a salad. After you grill the steaks, top with the tangy salad and serve. The oil can be made a day in advance but the steaks and tomatoes must be cooked at the last moment.
8 medium ripe red tomatoes, about 3 pounds ½ cup fresh chopped basil 1/3 cup extra virgin olive oil 1 small red onion, thinly sliced 3 tablespoons red wine vinegar 20 basil leaves, thinly sliced Coarse salt and freshly ground black pepper 6 small market, porterhouse or strip steaks, 6 to 8 ounces each
Cut the tomatoes in half crosswise and scoop out all of the seeds. Place the tomatoes, cut side down on paper towels and let drain, 1 hour. In a small saucepan, combine the chopped basil and 1/4 cup olive oil. Heat over low heat just until the oil sizzles. Remove from the heat and let sit until cool, 1 hour. Strain and discard the basil.
Heat a charcoal grill. Brush the cut side of the tomatoes with 2 tablespoons basil oil. Place on the grill, 3" from the heat source and grill until the flesh blackens, 4 to 5 minutes. Turn the tomatoes and char on the other side, 1 minute. Remove . Cut the tomatoes into 1" chunks and place in a bowl. Add the basil oil, red onion, vinegar, and thinly sliced basil. Season to taste with salt and pepper.
Oil the steaks and grill on one side until golden brown, 4 to 5 minutes. Turn the steaks, season with salt and pepper and continue to cook until medium rare, 4 to 5 minutes. Remove from the grill and place on individual plates. To serve, top with the charred tomato salad and serve immediately.
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