Ingredients

  • 3 quarts water
  • 2 tablespoons fennel seeds
  • 2 tablespoons black peppercorns
  • 2 tablespoons cumin seeds
  • 1 tablespoon anise seeds
  • 1 tablespoon red pepper flakes
  • 2 teaspoons salt
  • 5 bay leaves
  • 1 stalk celery, broken in half
  • 8 cloves garlic, peeled
  • 4 pounds frozen cleaned octopus, defrosted
  • 4 cloves garlic, crushed
  • 1/2 teaspoon red pepper flakes
  • 2 bay leaves, crushed
  • 1 tablespoon dried oregano
  • 1/3 cup olive oil
  • 1 lemon, zest removed with a vegetable peeler and coarsely chopped
  • 1/3 cup extra-virgin olive oil
  • Juice of 1 lemon
  • 1/4 cup white balsamic vinegar
  • 2 cloves garlic, minced
  • 1 tablespoon capers, rinsed and chopped
  • 10 Kalamata olives, pitted and coarsely chopped
  • 2 tablespoons golden raisins, plumped in hot water for 20 minutes and drained
  • Kosher salt and freshly ground black pepper
  • 3 cups arugula
  • 1 cup tom radicchio
  • 8 tom fresh basil leaves

Method

  • Combine the poaching liquid ingredients in a large stockpot and bring to a boil.
  • Add the octopus, reduce the heat to medium-low, and simmer until tender, 1 to 1 1/2 hours.
  • The meat is done when you can cut the thickest part of the tentacle with a butter knife.
  • Remove from the poaching liquid and let the octopus cool for 15 minutes.
  • Using your hands or a clean dishtowel, remove all the skin.
  • Combine the marinade ingredients in a medium bowl.
  • Add the octopus, tossing to coat.
  • Set aside at room temperature for 1 hour.
  • Combine the oil, lemon juice, vinegar, garlic, capers, olives, and raisins in a medium bowl.
  • Salt and pepper to taste.
  • Set aside.
  • Light a charcoal fire or preheat your gas grill on high.
  • Oil the grills cooking surface.
  • Remove the octopus from the marinade, letting the excess drain back into the bowl.
  • Discard the marinade.
  • Season the octopus with salt and pepper and place on the grill.
  • Cook for 5 to 7 minutes total, turning so that all the sides get slightly golden and crispy.
  • Remove to a cutting board, then cut the tentacles at an angle into 1/2-inch-thick pieces.
  • Toss with the salad dressing.
  • Add the arugula, radicchio, and basil, tossing well to combine.
  • Serve immediately.