Pat the pork shoulder with paper towel to remove excess liquid. Season with salt and pepper.
Add olive oil to a large oven-proof Dutch oven over medium-high heat.
Once the oil is hot, add the pork shoulder and brown on each side for 3-4 minutes each.
Remove the pork from the Dutch oven.
Add the onion, carrots, garlic, and Italian seasoning, and season with salt and pepper, to taste.
Cook the vegetables until softened, about 5-7 minutes.
Add the wine and cook for another 5 minutes, until slightly reduced.
Add the crushed tomatoes and diced tomatoes, and stir well to combine.
Return the pork to the Dutch oven, tucking it into the sauce.
Bring the mixture to a boil, reduce heat to low, and cover.
Let the mixture simmer for 3 ½-4 hours, until the pork is fork tender and easily shreddable.
Note: make sure the mixture is lightly simmering the entire time. If the heat is too low and the mixture isn't hot enough, the pork will likely not be done in 4 hours.
Once the pork is finished, shred the pork with two forks.
Serve rage with pasta, polenta, or gnocchi.
Top with shredded or grated Parmesan cheese and fresh parsley.
Enjoy!