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Add the bacon and 1 teaspoon oil to a saute pan and place over medium-high heat. Once the bacon starts to render, add the grapes. Allow the bacon to render and get crispy and the grapes to split open and release their juices. Remove half of the grapes and bacon and set aside. Add the port wine and red wine vinegar and reduce by half. Add the chicken stock and reduce by half.
To a cast-iron pan, add 2 tablespoons olive oil and heat over medium-high heat. Add the seasoned pork chops to the pan and sear. Cook the pork for 6 to 7 minutes on the first side. Flip over and reduce the heat. Cook for another 6 to 7 minutes until cooked through. Flip and cook the pork on the remaining sides for another 2 to 3 minutes each side. Remove the pork from the pan and allow it to rest for about 5 minutes prior to serving.