Dry the roast thoroughly and season it liberally with kosher salt and black pepper. Let it chill on a plate in the refrigerator, uncovered, for up to 24 hours.

Remove the roast from the fridge about 30 minutes prior to cooking. In a large Dutch oven, heat 2 tablespoons of olive oil over medium-high heat. Preheat your oven to 325°F.

Coat the roast in flour using a pie dish, then sear it in the hot oil for roughly 3-4 minutes on each side. Transfer the seared roast to a clean plate.

In the same pot, add the remaining olive oil. Incorporate the onions, carrots, celery, and smashed garlic, season with salt and pepper, and sauté, stirring occasionally, for about 5 minutes until the onions are translucent.

Pour in all the other sauce ingredients, excluding the butter and flour for the gravy. Place the seared roast back into the pot, cover with a lid or aluminum foil, and cook in the oven for 2 hours. Afterward, reduce the heat to 250°F and continue cooking for another hour or two.

Once cooking is complete, remove the Dutch oven from the oven. Place the meat and carrots onto a serving platter, shred the meat, and keep it warm under foil.

Blend the tomatoes with half of the sauce until smooth, then add it back to the pot. In a separate bowl, combine the softened butter and flour, then stir this mixture into the sauce. Simmer for 2-5 minutes until slightly thickened.

Serve the gravy over the shredded meat and vegetables.