Preheat a grill to high. Make the dressing: In a small sauté pan, warm 2 tablespoons olive oil over medium heat and add the fresh oregano. Cook until the green color fades and the leaves crisp up, 2 to 3 minutes. Pour the oil and oregano into a medium bowl. Add the remaining 2 tablespoons olive oil and the dried oregano to the bowl. Cut the limes in half and squeeze all the juice into the bowl. Use a citrus reamer or a spoon to scrape the pulp from the limes and add the pulp to the bowl as well. Whisk together. Taste for seasoning.
Grill the heirloom tomatoes: Oil the grill grates. Arrange the heirloom tomato slices in a single layer on 2 baking sheets. Season them on both sides with salt, pepper and some of the sugar. Put the cherry tomatoes on a separate baking sheet and season them with more salt, pepper and sugar. Use a pair of tongs to transfer the heirloom tomato slices to the grill, arranging them in a single layer. Let them sit until they get nice grill marks on the bottom (and a great charred flavor), 2 to 3 minutes. Turn them over and let them cook for a few minutes longer. Transfer the grilled tomatoes to a serving platter. Top with the cherry tomato halves.
Finish the salad: Drizzle the tomatoes with the dressing and sprinkle with salt. Taste a piece of tomato to check the seasoning. If it lacks sweetness, a sprinkle of sugar on the tomatoes can make all the difference. Serve immediately.
Cook’s Note
Cut tomatoes into thick slices for grilling — otherwise they’ll be hard to flip and may fall apart.
Tools You May Need
Photograph by Johnny Miller
Tools You May Need
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