For the Garlic Aïoli: In a mixing bowl, combine mayonnaise, lemon, and garlic. Taste and adjust seasoning with salt. Transfer to an airtight container and refrigerate.
For the Raisin Salmoriglio: In a food processor, pulse to combine raisins, vinegar, shallots, and olives until finely minced. Transfer mixture to a mixing bowl and stir in remaining ingredients. Taste and adjust seasoning with salt and fennel pollen. Transfer to an airtight container and refrigerate.
For the Guanciale Vinaigrette: In a large sauté pan over medium heat, render guanciale and prosciutto skin until crispy. Stir in tomato paste and cook 5 minutes. Add onion and garlic and cook until alliums are soft and translucent. Season with oregano, chile powder, sugar, pepper, and a pinch of salt. Deglaze pan with wine and cook until au sec. Transfer mixture to a mixing bowl and stir in remaining ingredients and 150 grams water. Taste and adjust seasoning with Chianti seasoning and salt. Transfer to an airtight container and refrigerate.
For the Octopus: Bring a large pot of water to a boil. Add octopus and cook until fork-tender. Transfer to a parchment paper-lined sheet tray and let cool. On a work surface, portion octopus into 1-inch pieces. Set aside.
To Assemble and Serve: In a fryer, heat oil to 385°F. Add Octopus and fry 1 minute, or until crispy on the outside and tender on the inside. Transfer to a mixing bowl and toss to coat in Raisin Salmoriglio. Set aside. Spread 1 dollop Garlic Aïoli in the middle of a serving plate. Top with fried Octopus. Drizzle with Raisin Salmoriglio and Guanciale Vinaigrette. Garnish with grilled cucumber, black lime, espelette pepper, and basil.
