HEIRLOOM TOMATO SALAD WITH PICKLED FENNEL

Heirloom Tomato Salad with Pickled Fennel image

Provided by Michael Anthony

Yield Makes 6 servings

Number Of Ingredients 22

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Pickled fennel:
1 whole star anise pod
1 teaspoon aniseed
1 teaspoon coriander seeds
1 teaspoon fennel seeds
1/4 teaspoon cumin seeds
1/4 lemongrass stalk, tough outer layer removed, crushed
Zest of 1/4 orange, removed with a vegetable peeler
1 medium fennel bulb, cored, thinly sliced
1 1/2 cups unseasoned rice vinegar
1/2 cup sugar
2 tablespoons kosher salt
Assembly:
2 pounds large heirloom tomatoes (about 3), cut into wedges
1 cup cherry tomatoes, preferably heirloom, halved
2 tablespoons white balsamic or Sherry vinegar
7 tablespoons extra-virgin olive oil, divided
Kosher salt, freshly ground pepper
2 Cubanelle peppers or Anaheim chiles, sliced into 3/4" rings, seeded
Fennel fronds (for serving)
Special Equipment
Cheesecloth

Steps:

For pickled fennel:
Toast star anise, aniseed, coriander seeds, fennel seeds, and cumin seeds in a small skillet over medium-low heat, stirring often, until fragrant, about 3 minutes. Bundle toasted spices, lemongrass, and orange zest in a piece of cheesecloth and tie with kitchen twine to make a sachet. Place sachet and fennel in a 1-quart jar or bowl.
Bring vinegar, sugar, salt, and 1/2 cup water to a boil in a medium saucepan, stirring to dissolve sugar and salt. Pour vinegar mixture over sachet and fennel and let cool; discard sachet. Cover fennel and chill at least 12 hours.
DO AHEAD: Pickled fennel can be made 2 weeks ahead. Keep chilled.
For assembly:
Combine large and cherry tomatoes, vinegar, and 6 tablespoons oil in a medium bowl; season with salt and pepper. Let sit at room temperature 30 minutes.
Before serving, heat remaining 1 tablespoon oil in a medium skillet over high heat. Cook Cubanelle peppers, tossing often, until charred in spots, about 4 minutes.
Serve tomato salad topped with peppers, pickled fennel, and fennel fronds.