Preheat your oven to 325 degrees.
Liberally sprinkle salt and pepper on the brisket.
In a large pan, heat the oil to medium-high heat. Add the brisket, fat side down, and cook until browned. About 5 minutes. Turn the brisket and cook the other side for another 5 minutes. Remove from heat and transfer the brisket, fat side up, to a roasting pan.
Add the garlic, onions, carrots and celery to the skillet and cook over medium heat until the onions turn translucent, about 10 minutes. Add the bay leaves and rosemary, and cook for one minute. Add the wine and broth, and bring to a boil. Cook until the liquid reduces by 25%, about 3 minutes. Add the tomatoes and turn down the heat until the liquids begin a slow simmer. Cook for 10 minutes and then pour over the brisket.
Cover the roasting pan with foil and place in the oven until the brisket is tender and the meat comes apart when poked with a fork, about 3 hours. Remove the pan from the oven. Transfer the brisket to a plate and cover with foil. Let sit for at least 30 minutes.
Remove the solids from the brisket cooking liquid. Taste the liquid and add salt and pepper if you like.
Carve the brisket into thin slices. Pour the sauce over the brisket to keep moist and juicy while it’s being served.