Melt the olive oil and butter in a Dutch oven set over medium-high heat. Generously season the pork shoulder with salt and pepper and place it in the pot, browning the meat on all sides, about 8–10 minutes in total.
While the meat cooks, set up the slow cooker. Remove the lid and place the chopped carrots, celery, onion and garlic on the bottom of the dish. Stir to combine. Lay the herbs on the vegetables and set the browned pork shoulder on top.
In a medium bowl whisk together the Hunt's Heirloom Crushed Tomatoes, red wine, Worcestershire sauce and fennel seeds. Pour the mixture over the pork and cover with a lid. Cook on high for 6–7 hours.
When the meat is cooked through and easily pulls away from the bone, it’s done. Transfer the pork to a plate, remove the herbs’ stems from the cooker, and pour the liquid and vegetables into the pot you used to brown the meat. Bring the sauce to a boil, lower the heat to medium and cook until the sauce is thick and reduced by about 1/3. While the sauce is cooking, remove the bone and excess fat from the pork and shred it using two forks. Put the meat back in the slow cooker and add the reduced sauce; stir to combine and cover.
Cook the pasta according to the package directions. Serve the pasta topped with the pork ragu and fresh grated Parmesan.