Ingredients

• 2 1/2 tablespoons (plus more for the pesto) olive oil
• 6 Italian fennel sausages, cut into 1/2-inch-thick slices
• 1 large onion, peeled and chopped
• 1 fennel bulb, trimmed and roughly chopped (reserve fronds to garnish)
• 1/2 teaspoon smoked paprika
• 1 garlic clove, peeled and sliced
• 2 teaspoons fennel seeds, lightly toasted and gently crushed
• 1/2 cup red wine
• 1 can (about 14 ounces) canned chopped tomatoes
• 1/2 teaspoon granulated sugar
• 1/3 cup pitted black olives, halved lengthwise
• 1 pound rigatoni
• 1 ounce (about 1/3 cup) pecorino, crumbled into small pieces
• 1 anchovy fillet, rinsed and patted dry
• 1 garlic clove, peeled and crushed
• 1/4 cup olive oil (for pesto)
• about 2 cups loosely packed fresh basil leaves, torn

Equipment

• Large saute pan with lid
• Large pot
• Small food processor
• Colander

Instructions

1. Heat 1 tablespoon of the olive oil in a large saute pan (one with a lid) over medium-high heat. Add the sausage slices and fry for about 10 minutes, stirring often, until they are golden-brown all over. This browning is where a lot of the sauce's flavor comes from, so do not rush it. Transfer the sausage to a plate.
2. Add the onion and chopped fennel to the hot pan and cook for about 15 minutes, stirring now and then, until soft and lightly caramelized. If the pan looks dry, add a teaspoon or so more oil. You want them sweet and golden, not raw and sharp.
3. Stir in the paprika, sliced garlic, and half the fennel seeds and cook for 2 minutes, until fragrant. Pour in the red wine and let it bubble for about 30 seconds to reduce by half, which cooks off the raw alcohol.
4. Add the tomatoes, sugar, 1/2 cup water, the browned sausage, and 1/2 teaspoon salt. Cover and simmer for 30 minutes, removing the lid after the first 10 minutes so the sauce can thicken. Cook until it is thick and rich.
5. Take the pan off the heat and stir in the olives and remaining fennel seeds. Set aside while you cook the pasta.
6. Bring a large pot of well-salted water to a boil, add the rigatoni, and cook for 12 to 14 minutes (or per the package), until al dente with a little bite. Reheat the sauce gently while the pasta cooks.
7. Make the pesto: put the pecorino, anchovy, crushed garlic, 1/4 cup olive oil, and 1 tablespoon water in a small food processor and blitz to a rough paste. Add the basil and pulse just until combined; overblending turns it dull, so keep it loose and textured.
8. Drain the pasta, return it to the pot, and toss with 1 tablespoon olive oil. Divide among bowls, spoon the sausage ragu over the top, and add a spoonful of pesto. Scatter with chopped fennel fronds if you saved any, and serve right away.