Preheat your oven to 325°F (163°C).
In a large Dutch oven or heavy pot, heat the olive oil over medium-high heat. Season the beef chuck roast with salt and pepper, then sear it in the hot oil for about 4-5 minutes on each side until browned. Remove the roast and set it aside.
In the same pot, add the chopped onion, garlic, carrots, and celery. Sauté for about 5-7 minutes until the vegetables are softened.
Stir in the diced tomatoes, beef broth, red wine (if using), tomato paste, oregano, basil, and bay leaves. Bring the mixture to a simmer.
Return the seared roast to the pot, ensuring it is submerged in the liquid. Cover the pot with a lid and transfer it to the preheated oven.
Cook for 3-4 hours, or until the beef is tender and easily shreds with a fork.
Once cooked, remove the pot from the oven. Take out the roast and let it rest for a few minutes before shredding it with two forks.
Discard the bay leaves and return the shredded beef to the pot, stirring to combine with the sauce.
Serve hot, garnished with fresh parsley.