If you can't find fresh octopus, frozen octopus works perfectly well for this dish. Some cooks even prefer it, because freezing tenderizes it.
1 medium octopus, about 2 1/2 lbs.
1 cup extra-virgin olive oil
1 1/2 cups Cretan red wine, or other dry red wine
8 oz. wild fennel, cut into 2'' pieces (or substitute 1 large
bulb regular fennel, trimmed and coarsely sliced, along
with some of its tender green fronds)
1 tsp. toasted ground fennel seeds
1 small bunch coarsely chopped fresh dill
8 oz. cracked green olives, or other small whole green olives
1. Ask your fishmonger to clean octopus for you, or follow these instructions: Rinse octopus, then cut off its head (which is also its body) and carefully remove and discard ink sac and innards. Use a small paring knife to cut out eyes, then discard. Turn the cluster of tentacles over and, squeezing the center, push out the beak, then carefully cut it away and discard it. Use kitchen shears to cut apart tentacles. Rinse octopus, then blot dry with paper towels and set aside.
2. Heat 1/4 cup of the oil in a large, heavy-bottomed pot over medium-high heat, add octopus, and cook, turning occasionally, until it releases its juices. Continue cooking until juices have reduced by two-thirds and have thickened to a rich purple syrup, about 30 minutes. Add wine, and bring to a boil. Cover, and reduce heat to medium-low. Simmer until tender, about 1 hour.
3. Heat remaining 3/4 cup of the oil in a large pot over high heat. Add wild fennel and sauté for 5 minutes, stirring occasionally. Lower heat to medium and add 1 cup water. Cover and simmer until fennel is just tender, about 20 minutes, adding more water if needed. (If using fennel, fennel seeds, and dill add only 1/2 cup water and cook until fennel is just tender, about 8-10 minutes). Add octopus and all the liquid to the fennel, return to a simmer over medium heat, and cook for 15 minutes more. Add olives and cook for 5 minutes more.