Trim some of the fat from the meat. Pat dry with paper towels. Season generously with the salt and pepper. Heat the oil in a large, heavy pot or Dutch oven over medium-high heat.

When the oil is hot, add the roast and cook, turning it until it is nicely browned on all sides, about 10-12 minutes. Transfer the meat to a platter.

Reduce the heat to medium. Add the carrot, celery, and onion. Cook, stirring occasionally until the vegetables are golden brown and begin to stick to the bottom of the pan, 10-12 minutes.

Add the garlic, parsley, and sage, and stir until the herbs are lightly colored and fragrant, about 1 minute.

Add 1 cup of the wine and stir quickly, lifting up the caramelized vegetables that stick to the bottom.

When the wine is almost all evaporated, return the meat to the pan and turn it to coat with the savory base.

Raise the heat to high, adding the remaining wine, bay leaf, and tomatoes, and bring to a boil.

Cover the pot, reduce the heat to low, and simmer, turning and basting the meat every half hour until very tender, about 3-4 hours.

Turn off the heat and let the roast sit in its juices for an hour.

Remove the meat from the pot and place it on a cutting board, covered loosely with aluminum foil.

If the sauce is too thin, bring it to a fast boil and reduce until medium-thick. Taste and adjust seasoning.

Cut the meat into thick slices, place on warm serving dishes, and spoon the sauce over the meat to serve hot.