One glorious fall day last year, we visited the winemaker Vangelis Gerovassiliou in Epanomi, near the city of Thessaloniki. His mother, kyria (Mrs.) Marianthi, made this delicious local specialty for us. "Food needs olive oil," she said matter-of-factly when I remarked on the copious amount of olive oil in the dish. She also explained that she bakes the dish, rather than cooking it on the stovetop, to prevent the eggplant from disintegrating. Contrary to my own inclination, she also boils the octopus.
Fill a large bowl or basin with warm water, add the vinegar, and soak the octopus for a few minutes. Rinse well. Using a sharp knife, cut off the octopus's hood just below the eyes and discard. With a small paring knife, remove its beak and cartilaginous mouthpiece. Rinse and drain the octopus.
Put the octopus in a large pot with enough water to cover. Add the allspice and 3 of the bay leaves. Bring to a boil, reduce the heat, and simmer until the octopus is somewhat tender but still firm to the touch, for 40-50 minutes.
Remove from the heat, and remove the octopus from the pot. Reserve ½ cup of the cooking liquid and discard the rest. Cool the octopus slightly, and cut into 8 pieces along the tentacles. Set aside.
Preheat the oven to 350 degrees.
Meanwhile, heat the olive oil in a large, heavy frying pan over medium heat and sauté the eggplants for a few minutes, until al dente. Remove the eggplants from the frying pan with a slotted spoon and set aside.
Add the tomatoes to the pan and cook over medium heat until most of their liquid has cooked off and the tomatoes are thick. Remove from the heat. Put the eggplant in a large baking pan, add the octopus, tomato, and remaining bay leaves, and toss together. Season with salt and pepper, to taste, and add the reserved octopus cooking liquid. Drizzle with olive oil and bake, uncovered, for about 25 minutes. Remove the bay leaves and serve.