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Season the pork shoulder with salt and pepper. Place a cast iron dutch oven (or heavy bottomed pot) over medium-high heat and add oil to cover the bottom. When hot, add the pork to the pot and brown on all sides, about 5 minutes per side. Remove the pork from the pot and reserve.
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Reduce the heat to medium and crumble the sausage into the pot. Sauté for about 6 minutes, breaking up any large chunks, until there is no more pink remaining. Remove the sausage from the pot and set aside.
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Reduce heat to medium-low and add onion, carrot, celery, garlic, rosemary, thyme, sage, bay leaves, and chili to the pot. Sauté the vegetables for about 10 minutes. Add tomato paste and stir. Pour in the wine and simmer until reduced by half. Place the pork and sausage back into the pot and pour in the can of tomatoes.
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Reduce the heat to low, cover and let simmer for 4 hours, turning every hour or so.
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Carefully remove the pork from the pot and place on a cutting board. Using two forks, shred the pork into bite size pieces (discard the fat and bones). Return the shredded pork into the pot and taste for seasoning (add salt and pepper if needed).
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Bring a large pot of water to boil and add salt. Add the pasta and cook until al dente. Drain and reserve.
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Transfer the ragu into a large skillet over medium heat. Add the pasta and toss to coat. (Note: Add a little bit of pasta water if the sauce seems too dry.)
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Transfer the pasta to plates, top with additional ragu, grated parmesan, and freshly cracked black pepper.
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Enjoy!