Preheat your oven to 375°F (190°C). Season the chuck roast generously with salt and pepper. In a large, oven-safe pot, heat up some neutral cooking oil over medium-high heat. Sear the roast for 4-5 minutes on each side until a rich, brown crust develops.

Remove the beef from the pot and set aside. Melt 2 tablespoons of butter in the same pot. Add finely chopped yellow onions and sauté for 5-7 minutes until caramelized. Toss in the whole garlic bulb, cooking for another 1-2 minutes until fragrant.

Pour in 1 cup of red wine to deglaze the pot, bringing it to a boil for about 2 minutes. Add whole peeled tomatoes and 1 ½ cups of beef stock, seasoning with salt, pepper, and crushed red pepper to taste.

Place the browned chuck roast back into the pot, ensuring garlic is on top of the beef. Cover and transfer to the oven. Braise for 3 hours.

After cooking, remove from the oven and take out the garlic bulb, squeezing in the roasted garlic into the sauce. Shred the beef into bite-sized pieces and mix back into the sauce. Simmer on low heat for another 30 minutes.

Bring 4 cups of water to a boil in a separate saucepan. Gradually whisk in 1 cup of yellow grits and reduce heat. Stir for 5-7 minutes until thick, add 1 cup of whole milk, and cook for another 5 minutes. Mix in shredded cheese, cayenne, and paprika.

Ladle cheesy grits into bowls, topping with the rich, shredded beef mixture. Enjoy warm for a cozy meal!