Season the roast generously with salt and pepper. Heat olive oil in a Dutch oven over medium-high heat and sear the roast on all sides for about 3–5 minutes each side.
Add the chopped onion, carrots, and celery to the pot. Cook until softened for about 5–7 minutes before adding minced garlic.
Stir in crushed tomatoes, beef broth, apple vinegar, tomato paste, oregano, basil, salt, and black pepper. Bring this mixture to a gentle simmer.
Return the seared roast to the pot. Cover it up tightly and place it in a preheated oven at 325°F (163°C). Let it cook for about 2½–3 hours until fork-tender.
Let the roast rest for about ten minutes after removing it from the oven before shredding it with two forks.
In a separate saucepan over medium heat, heat olive oil again and sauté finely chopped shallot until softened (about 3–5 minutes).
Add Arborio rice to your saucepan; toast it by stirring constantly for about 2–3 minutes.
Pour in dry white grape juice; stir until completely absorbed by the rice.
Start adding hot chicken broth one cup at a time to your rice mixture. Stir continuously until each addition is absorbed before adding more.
Once you've reached your desired consistency with risotto, stir in grated Parmesan cheese along with butter. Season with salt and pepper according to taste.