For the pork: In a small bowl, combine the garlic, rosemary, sage and crushed red pepper with 1/2 cup olive oil. Sprinkle the pork generously with salt and brush both sides with the olive oil herb paste.
Stand the pork rack up and curl it around so that the two ends meet; be sure that the thick meaty part of the pork is on the inside. Secure the roast by tying it twice around the outside of the roast with twine.
Place the pork in a large roasting pan fitted with a pizza pan tray and stuff the center of the pork with the Pear and Chestnut Stuffing. (There will be leftover stuffing. Place the leftover stuffing in a baking dish and cook for 35 minutes at 350 degrees F.)
For the pan sauce: Place the garlic and diced veggies around the pork. Add half the chicken stock, the wine and bay leaves to the pan. Sprinkle everything with salt.
Cover the pork bones with aluminum foil to prevent the bones from burning. Place the pork in the oven. Roast until the pork is starting to brown, about 30 minutes.
Turn the oven down to 325 degrees F.
Roast the pork for 2 1/2 more hours, basting the pork occasionally. Rotate the pork a couple of times during the cooking time. If the liquid level reduces, replace it with the remaining stock.
When the pork is cooked to the proper doneness - an instant-read thermometer should read 140 to 145 degrees F - remove it from the oven. Carefully transfer the pork to a serving platter and cover it loosely with aluminum foil. Let the pork rest for 20 to 25 minutes.
Bring the pan juices to a boil. Taste and re-season if needed. Blend the veggies if desired to create a smoother sauce. I also like to leave them in.
To serve: Remove the twine. Scoop out the stuffing and cut the pork in between the bones to create chops. Top with pan sauce.
Chestnut and Pear Stuffing:
Coat a wide, straight-sided pan with olive oil and add the bacon. Bring the pan to a medium heat and let the bacon get brown and crispy.
Add the celery, onions and fennel and season with salt. Cook the veggies until they get soft and very aromatic, 8 to10 minutes. Add the rosemary and garlic and cook for 1 to 2 minutes more.
Toss in the chestnuts, cranberries and pears, and stir to combine. Add the wine and let it reduce by half.
Put the bread in a large mixing bowl and add the cooked veggie mixture to the bread. Stir to combine and douse the bread with half the stock. Use your hands to combine the bread, veggies and stock. Add more stock when/if needed to really saturate the bread. Season with salt and taste it to make sure it is delicious.