Directions

1. Bring a pot of salted water to a boil over high heat. Prepare an ice-water bath. Add broccoli rabe to boiling water and cook until tender, 3 to 5 minutes. Drain and immediately transfer to ice-water bath until cool. Drain and transfer to the bowl of a food processor along with, 2 cloves garlic and pine nuts. Season with salt and pepper and process pesto until smooth.
2. With the machine running, slowly add 3/4 cup olive oil. Transfer pesto to a medium bowl and stir in Parmesan.
3. Bring a large pot of salted water to a boil over high heat. Add pasta and cook, until al dente, according to package directions.
4. Meanwhile, heat remaining 3 tablespoons olive oil in a large skillet over medium-high heat. Slice remaining 2 garlic cloves and add to skillet along with pepper flakes; cook, stirring, for 1 minute. Add calamari and olives; cook, stirring, for 30 seconds. Add wine and cook until almost evaporated.
5. Drain pasta, reserving 1/2 cup cooking liquid; add pasta and reserved liquid to skillet. Add 1 cup pesto (reserving remaining pesto for another use) and toss until pasta is coated. Divide evenly between 4 bowls; serve immediately.