Grilled Octopus with Ancho Chile Sauce

In this dish, the octopus is first braised in sherry and then the skin is removed to make it extra-tender before it’s finished on the grill and glazed with a tangy ancho chile sauce.

Octopus:
2 Tbsp. extra-virgin olive oil
1 octopus, head and tentacles separated, cleaned
3 shallots, thinly sliced
3 cloves garlic, thinly sliced
1 Tbsp. sweet pimentón de la Vera (smoked paprika)
2 cups dry sherry

Ancho Chile Sauce:
3 ancho chiles, stemmed and seeded
1 small dried chipotle chile, stemmed and seeded
¾ cup apple cider vinegar
3 Tbsp. honey
1 clove garlic
¼ cup + 2 Tbsp. grapeseed or canola oil
sea salt
Canola oil, for brushing
Jicama Salad, for serving

Preheat the oven to 300°F.

In a large enameled cast-iron casserole, heat the olive oil. Add half of the octopus and cook over moderately high heat, turning, until lightly browned all over, 3 to 5 minutes. Transfer to a plate. Repeat with the remaining octopus.

Add the shallots and garlic to the casserole and cook over moderate heat, stirring, until lightly browned, about 2 minutes. Add the pimentón and cook, stirring, until fragrant, about 20 seconds. Carefully add the sherry and bring to a boil. Return the octopus to the casserole, cover and braise in the oven until very tender, about 1 hour and 30 minutes. Let the octopus cool completely in the liquid.

Make the sauce: In a medium saucepan, toast the chiles over moderate heat, turning, until fragrant and pliable, 2 to 3 minutes. Add the vinegar, honey and garlic and bring just to a simmer. Remove from the heat and let stand until the chiles are softened, about 20 minutes. Transfer to 
a blender and puree until smooth. With the machine on, gradually add the grapeseed oil until incorporated. Season the ancho chile sauce with salt.

Remove the octopus from the liquid. Using a paper towel, wipe the purple skin off the 
tentacles, leaving the suckers intact. Cut the head in half. 
Discard the braising liquid.

Light a grill or preheat a grill pan and brush with canola oil. Grill the octopus over high heat, turning, until lightly charred all over, about 4 minutes. Transfer to a baking sheet and immediately brush with some of the ancho chile sauce. Serve with the jicama salad, passing the remaining sauce at the table.

Make Ahead: The recipe can be prepared through Step 4; refrigerate the octopus and ancho chile sauce separately for up to 3 days.

Suggested Pairing: Dry, fruit-forward rosés can help cut the heat in spicy dishes like this octopus.

Makes 6 servings.