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Remove the leaves and outer stems from the cauliflower, then slice the head into three cross sections, keeping the core of each section intact. Drizzle both sides of each piece with olive oil and season all over with salt and black pepper.
Prepare a grill for medium-high heat. Grill the cauliflower until each side has begun to brown and the core can be easily pierced with a small knife, about 5 minutes per side. (The cauliflower should be al dente, not soft.)
While the cauliflower is cooking, place the kale in a large bowl and toss with the kumquats and red onions. Once the cauliflower has reach the desired doneness, cut the florets from the cores. Add the florets to kale mixture (reserve the cores for another use).
Drizzle the kale mixture with half the vinaigrette and toss well. Season with salt and black pepper and allow to rest for 10 minutes. After 10 minutes, adjust the seasoning as needed and add more vinaigrette if desired.