Preheat your oven to 325°F. In a large Dutch oven, 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. Stir in the garlic and cook for an additional minute.

Pour in the red wine, scraping up any browned bits from the bottom of the pot. Let it simmer for about 2 minutes. Add the diced tomatoes, beef broth, oregano, basil, bay leaf, and the seared roast back into the pot.

Cover the pot and transfer it to the preheated oven. Cook for 3 to 4 hours, or until the meat is tender and easily shredded with a fork.

While the roast is cooking, prepare the polenta. In a medium saucepan, bring 4 cups of water to a boil. Slowly whisk in the polenta, stirring constantly to prevent lumps. Reduce heat to low and cook for about 20-25 minutes, stirring frequently until thickened.

Once the polenta is cooked, remove it from heat and stir in the Gorgonzola cheese, Parmesan cheese, and butter until melted and creamy. Season with salt and pepper to taste.

When the roast is done, remove it from the oven and let it rest for a few minutes. Shred the meat with two forks and return it to the pot, mixing it with the sauce.

Serve the shredded pot roast over a generous scoop of Gorgonzola polenta. Garnish with fresh parsley.