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Tomato Squash Salad

maddie July 16, 2020 0 Comments


YIELD: Serves 2-3

TIME: 30 minutes

From sprinkling flaky salt on a thick-cut heirloom, to snacking on little sungolds like we’re snacking on popcorn, we believe there is no wrong way to eat a tomato. But there are many ways to eat them right. When combined with at least one (if not all) of the following — salt, olive oil, fresh basil, garlic, Duke’s mayonnaise, lemon or cheese — tomatoes can never lose. Which makes salad a real winner: it hits each and every one of those ace tomato accompaniments, making it possibly the best tomato salad on planet earth. This salad goes beautifully with a simply seasoned and beautifully grilled steak, a fresh baguette from your favorite local baker, and a chillable red wine.


1 medium-large tomato, any variety
2 squash (yellow, striped, or whatever you like best)
Kosher salt
Freshly ground black pepper
1 garlic clove, microplaned or grated
2 tablespoons Duke’s mayonnaise
1 – 2 teaspoon lemon juice
2 – 3 tablespoons of your favorite soft herbs, rough chopped or torn (basil, parsley, chives, oregano, dill, or cilantro)
½ fennel bulb
2 – 4 tablespoons fat (butter, olive oil, avocado oil, bacon fat, or whatever you have on hand)
¼ cup castelvestrano olives, pitted and sliced or rough-chopped
Freshly grated Pecorino or Parmesan cheese

Tomato Squash Salad
  1. Slice the squashes in half, lengthwise. Season the cut side with salt and pepper and set aside.

  2. Using the tip of your serrated tomato knife, carefully remove the core. Slice the tomato in half, and then slice each half into thin ¼” wedges. Carefully transfer to a bowl and season with salt and pepper. Add grated garlic, mayonnaise, lemon juice, and soft herbs. Gently mix to combine and set aside.

  3. Heat a cast iron skillet to medium heat. While it’s heating up, prepare the fennel: face it cut-side down and, leaving a bit of the core in-tact to keep it from falling apart, slice fennel into ¼” slices. Season with salt.

  4. Once the cast-iron is hot, melt 2 tablespoons of fat in the pan and spread fennel out in an even layer so that every piece is touching the surface of the pan. Lay another cast-iron skillet on top to press the fennel down, ensuring a hard sear. Cook for 5 – 8 minutes, or until golden brown. Once golden and beautiful, remove from pan and set aside to cool. Leave fennel pieces as-is with the root piece in-tact, or feel free to chop the root off, creating smaller fennel pieces. Add fennel to tomato; stir gently to combine.

  5. Increase heat on cast iron to medium-high. Use a paper towel to pat the squash dry, removing any excess moisture the salt may have drawn out. Once skillet is hot, add another tablespoon of fat to the pan if necessary, and then lay the squash cut side down onto the pan. Just like the fennel, set secondary cast iron and set on top to get a sear across the entire surface. Cook until color is golden brown, 5 – 10 minutes. Once golden color is reached, turn heat down to medium-low and let squashes finish cooking until tender but not falling apart; about 4-5 minutes more. Remove from heat and cool. Once squash has cooled enough to touch with your fingers, slice each half into half-inch moons.

  6. Use a slotted spoon to strain tomato-fennel mixture from their juices, reserving the liquid for later. In your favorite serving bowl, create a long mound of tomato-fennel mixture on one side, and do the same with the squash on the other side.

  7. Scatter olives on top and use a micro-plane to shave Pecorino or Parmesan cheese across the surface of the salad. Feel free to drizzle reserved tomato-fennel liquid on top for additional dressing, or reserve for another use.

Tomato Squash Salad
AboutMaddie Adams

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