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1
In a large enameled cast-iron casserole, heat 2 tablespoons of the olive oil.
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2
Add the octopus and cook over moderately high heat, turning, until lightly browned all over, 2 to 3 minutes.
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3
Transfer the octopus to a plate.
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4
Add the garlic cloves to the casserole and cook over moderate heat, stirring, until lightly browned, about 2 minutes.
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5
Add the crushed red pepper and cook, stirring, until fragrant, about 20 seconds.
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6
Carefully add the white wine and bring to a boil.
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7
Return the octopus to the casserole; if necessary, add up to 1 cup of water to cover the octopus.
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8
Cover the casserole and braise over moderately low heat until very tender, about 1 hour and 30 minutes.
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9
Transfer the octopus to a plate and let cool completely.
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10
Meanwhile, in a large bowl, whisk the red wine vinegar with the lemon juice, oregano and 2 tablespoons of the olive oil.
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11
Add the fennel, carrot, onion, scallions, chickpeas and a generous pinch of salt and mix well.
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12
Let stand for 30 minutes or up to 4 hours, stirring occasionally.
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13
Stir in the parsley and season the salad with salt.
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14
Using a paper towel, wipe the purple skin off the octopus tentacles, leaving the suckers intact.
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15
Cut the tentacles in half lengthwise, then cut them into 3-inch lengths.
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16
Cut the head into 1 1/2-inch pieces.
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17
In a large skillet, heat the remaining 2 tablespoons of olive oil.
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18
Add the octopus cut side down and cook over moderately high heat until well-browned on the bottom, about 1 minute.
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19
Turn the octopus and cook for 20 seconds longer.
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20
Transfer the seared octopus to a paper towellined plate to blot any excess oil and season lightly with salt.
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21
Transfer the octopus to plates.
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22
Fill the radicchio leaves with the Italian salad and set beside the octopus.
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23
Garnish with fennel fronds and serve.