How to Make It
Preheat the oven to 450°. In a medium bowl, toss the calamari with 2 tablespoons of the olive oil and the crushed red pepper; season the calamari with salt and black pepper.
On a large, rimmed baking sheet, toss the garlic with the remaining 2 tablespoons of olive oil. Roast the garlic on the top shelf of the oven for about 4 minutes, or until lightly golden. Toss the calamari with the garlic and roast for about 3 minutes, until opaque and firm. Strain the calamari juices into a small bowl and whisk in the vinegar.
In a medium bowl, toss the greens with the dressing and season with salt and pepper. Mound the greens on plates, top with the calamari and serve.