Squid Ink Pasta with Octopus & Tomato Sauce

• 1 ½-2 pounds octopus tentacles
• 2 cups white wine
• 4 garlic cloves
• 1 teaspoon dried basil
• 1 bay leaf
• 1 wine bottle cork
• 12 ounces Carbe Diem angel hair pasta
• 2 ounces squid ink
• Olive oil, for brushing

Tomato Sauce: 

• ¼ cup olive oil
• 1 small yellow onion, chopped
• 4 garlic cloves, minced
• 2 pounds fresh tomatoes, chopped
• ¼ cup fresh basil leaves
• 2 teaspoons red pepper flakes (optional)
• 1 teaspoon kosher salt
• ½ teaspoon ground pepper

1. If needed, tenderize your octopus: freeze until firm, then thaw. Check with your fishmonger if this has already been done. 
2. Cook the octopus: Place white wine, garlic, basil, bay leaf and wine cork (this helps tenderize the octopus) in a large skillet over medium-high heat. Add octopus tentacles and enough water to cover them. Bring to a boil, then reduce heat to medium-low and simmer for 30-40 minutes, until tentacles are tender when pierced with a knife. Let octopus cool completely in liquid, about 1 hour. 
3. While the octopus is cooking, make the tomato sauce: Heat olive oil in a saucepan over medium heat. Add onion and cook until softened and golden brown, 8 to 10 minutes. Add garlic and cook for 1 minute more. Add tomatoes, basil and red pepper flakes, if using, and stir until combined. Decrease heat to medium low and cook until tomatoes have broken down and sauce is simmering, about 30 minutes. Season with salt and pepper. If desired, blend or pulse in a food processor until smooth.
4. When ready to serve, bring a large pot of salted water to boil. Cook angel hair pasta until al dente according to package directions, 13 to 15 minutes. Drain, then return pasta to pot and toss immediately with squid ink.
5. If desired, brush octopus with olive oil and grill or brown in a cast iron skillet over medium-high heat until lightly charred, about 6 minutes per side. 
6. Divide pasta among serving bowls. Top with octopus and tomato sauce.