In a large bowl, combine bourbon, brown sugar, salt, black pepper, and chopped apples. Mix well until sugar and salt dissolve. Submerge the pork shank in the brine, cover, and refrigerate for at least 12 hours, or overnight.

Cook the Pork Shank

Preheat the oven to 300°F (150°C). Remove the pork shank from the brine and pat dry. In a large oven-safe pot, heat olive oil over medium-high heat. Sear the pork shank on all sides until browned. Add 1 cup of water, cover, and place in the oven. Cook for 3 hours, or until tender.

Prepare the Whipped Potatoes

While the pork is cooking, boil the cubed potatoes in salted water until tender. Drain and return to the pot. Add butter and milk, and whip until smooth and creamy. Season with salt and pepper to taste.

Braised Cabbage

In a large skillet, heat olive oil over medium heat. Add shredded cabbage, apple cider vinegar, caraway seeds, salt, and pepper. Sauté for about 10-15 minutes until the cabbage is tender and caramelized.

Serve

Once the pork shank is tender, remove it from the oven and let it rest for 10 minutes. Slice and serve alongside whipped potatoes and braised cabbage.