Season the boneless beef chuck roast generously with salt and black pepper. In a Dutch oven, heat 2 tablespoons of olive oil over medium-high heat, and sear the roast for 3–5 minutes on each side until it develops a deep brown crust. Once browned, remove the roast from the pot and set aside while you prepare the vegetables.

In the same pot, add chopped onion, carrots, and celery. Sauté the aromatic mix, stirring frequently, for about 5–7 minutes until they turn soft and translucent. Then, add minced garlic, letting it cook for an additional minute until fragrant.

Stir in the crushed tomatoes, beef broth, tomato paste, dried oregano, and basil, along with a pinch of salt and black pepper. Bring this mixture to a gentle simmer, allowing all the ingredients to meld together beautifully.

Carefully return the seared roast to the pot, ensuring it's surrounded by the rich sauce. Cover the Dutch oven and place it in a preheated oven set to 325°F. Let it braise for 2½–3 hours, until the meat is fork-tender and easy to shred.

While the roast is braising, heat another tablespoon of olive oil in a separate saucepan over medium heat. Sauté the shallot until it becomes translucent, about 3–5 minutes. Next, add Arborio rice to the pan, toasting it for 2–3 minutes while stirring constantly.

Gradually add hot chicken broth to the rice, one cup at a time, stirring frequently until almost absorbed. Continue this process for about 20–25 minutes, ensuring the risotto becomes creamy. Stir in grated Parmesan cheese and butter, seasoning with salt and pepper to taste.

Plate the tender pieces of pot roast over a generous serving of creamy Parmesan risotto, allowing some of that rich tomato sauce to cascade over the top.