Heirloom Tomato Salad with Pickled Fennel

Pickled Fennel
1 whole star anise pod
1 tsp. aniseed
1 tsp coriander seeds
1 tsp fennel seeds
¼ tsp cumin seeds
¼ lemongrass stalk, tough outer layer removed, crushed
zest of ¼ orange, removed with vegetable peeler
1 medium fennel bulb, cored, thinly sliced
1 ½ cup unseasoned rice vinegar
½ cup sugar
2 Tbsp. kosher salt

Pickled fennel: Toast star anise, aniseed, coriander seeds, fennel seeds, and cumin seeds in a small skillet over medium heat, stirring often, 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 qt jar or bowl.

Bring vinegar, salt, sugar, and ½ cup water to 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.

Pickled fennel can be made 2 weeks ahead. Keep chilled.

2 lb large heirloom tomatoes (about 3), cut into wedges
1 cup cherry tomatoes, preferably heirloom, halved
1 Tbsp. white balsamic or sherry vinegar
7 Tbsp extra virgin olive oil, divided
kosher salt, black pepper
2 Cubanelle peppers or Anaheim chiles, sliced into ¾” rings, seeded fennel fronds(for serving)

Assembly: Combine large and cherry tomatoes, vinegar, and 6 Tbsp, Oil in a medium bowl; season with salt and pepper; season with salt and pepper. Let sit at room temperature 30 minutes.

Before serving, heat remaining 1 Tbsp. oil in a medium skillet over high heat. Cook peppers, tossing often, until charred in spots, about 4 minutes.

Serve tomato salad topped with peppers, pickled fennel, and fennel fronds.