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Cook the kale in the boiling water for 4 to 5 minutes. Drain and rinse under cold running water, then squeeze dry and set aside.
Add 5 tablespoons olive oil to a large saute pan over medium-high heat. Once hot, add the guanciale and cook until it beings to crisp up. Then toss in the garlic, and continue to cook until it starts to turn golden. Add the red pepper flakes and saute for just 1 minute. Add the kale and toss for 2 minutes. Remove the pan from the heat and set aside.
Sprinkle the pork chops on both sides with salt and pepper. Heat a large saute pan over medium-high heat. Add the remaining 2 tablespoons olive oil and once hot, add the pork chops. Cook for 4 minutes, then flip and cook another 4 minutes. Remove the pork chops from the pan and reserve on a plate. Then add the wine to the hot pan and scrape the bottom with a wooden spoon to release any of the browned bits. Cook for 2 minutes, then add the pork chops back to the pan and cook for 1 more minute.