Heat oil in the bottom of a heavy Dutch oven until it almost smokes. Season the brisket with salt and pepper. Carefully lay brisket in pot, fat side down. When browned, flip over.
Cut garlic head in half across the cloves. Chop onion, celery and carrots into 2" pieces. Tie thyme, rosemary, parsley and bay leaf together with cotton twine to form a bouquet garni.
When browned, remove meat to a plate. Put the onion, garlic, celery, carrot and bouquet garni into the pot and allow to caramelize and cook down, 10-15 minutes.
Add tomatoes, beef broth and red wine to pot. Stir well, scraping up any browned bits (fond) at the bottom of the pot. Return meat (and any accumulated juices) to the pot. Cover tightly and bake in a preheated 325°F oven for 3 hours.
Remove brisket from pot to a platter. Let rest 10 minutes, then slice across the grain. Strain the juices from the pot, discarding the solids, and serve alongside the meat.