Preheat your oven to 300°F (150°C).

Pat the brisket dry with paper towels. Season generously with salt and freshly ground black pepper on both sides.

In a large Dutch oven, heat the olive oil over medium-high heat. Once hot, add the brisket and sear for about 4-5 minutes on each side until browned. Remove brisket from the pot and set aside.

In the same pot, add the diced onion and crushed garlic. Sauté for about 3-4 minutes until the onion is translucent. Stir in the chopped rosemary and smoked paprika, cooking for an additional minute until fragrant.

Pour in the beef broth and canned crushed tomatoes. Stir well to combine. Add the bay leaf and brown sugar.

Place the seared brisket back into the pot, ensuring it is submerged in the liquid. Drizzle the red wine vinegar over the top.

Cover the Dutch oven with a lid and transfer it to the preheated oven. Braise for 3-4 hours, or until the brisket is fork-tender.

Once the brisket is done, remove it from the pot and let it rest. Strain the cooking liquid into a saucepan, discarding the solids. Bring to a simmer over medium heat and cook until slightly thickened, about 10-15 minutes.

Slice the brisket against the grain and serve it with the velvety smoked tomato gravy drizzled over the top.