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 until browned on all sides, about 4-5 minutes per side. Remove the roast and set aside.

In the same pot, add the chopped onion, carrots, and celery. Sauté for about 5 minutes until the vegetables are softened. Add the minced garlic and cook for an additional minute.

Pour in the red wine, scraping the bottom of the pot to deglaze and lift any browned bits. Allow the wine to simmer for 2-3 minutes.

Return the beef roast to the pot. Add the beef broth, diced tomatoes, oregano, basil, and bay leaves. Bring the mixture to a simmer.

Cover the pot with a lid and reduce the heat to low. Let it cook for 3 to 4 hours, or until the meat is tender and easily shreds with a fork.

Once cooked, remove the roast from the pot and let it rest for a few minutes before slicing or shredding. Discard the bay leaves.

Serve the pot roast with the vegetables and sauce, garnished with chopped parsley.