Heat 2 tablespoons of olive oil in a Dutch oven over medium-high heat. Season the beef chuck roast with salt and pepper, then carefully place it in the pot. Sear the roast for about 4-5 minutes on each side until it's evenly browned.

Once the beef is browned, remove it from the pot and set it aside. In the same pot, add a chopped onion and 3 minced garlic cloves. Sauté for about 5 minutes until the onions become translucent.

Pour in 1 cup of red wine to deglaze the pot, stirring well for about 2-3 minutes. Allow the wine to simmer to enhance the depth of your pot roast.

Next, pour in 2 cups of beef broth, along with one 14-ounce can of diced tomatoes and 1 tablespoon of Italian seasoning. Stir well and return the seared beef to the pot. Cover and simmer for about 2 hours.

In a separate saucepan, melt 2 tablespoons of butter over medium heat. Add 1 cup of Arborio rice and stir continuously for 2-3 minutes.

Warm up about 4 cups of chicken broth. Gradually add it to the rice, one ladleful at a time, stirring continuously for around 20-30 minutes until creamy and al dente.

Once the risotto reaches the perfect creamy consistency, stir in 1 cup of grated Parmesan cheese.

Slice the fork-tender pot roast and plate it alongside the creamy Parmesan risotto. Garnish with freshly chopped parsley.