2 pounds boneless, well-marbled pork shoulder, cut into 2-inch cubes
Salt and freshly ground pepper
4 garlic cloves, smashed
1 large onion, cut into 1/2-inch dice
1 teaspoon ground fennel
2 tablespoons tomato paste
1 1/2 cups dry red wine, preferably Morellino di Scansano
2 cups chicken stock or low-sodium broth
2 medium carrots, sliced 1/4 inch thick (about 8 ounces)
3/4 cup pitted Gaeta olives
4 thyme sprigs
2 bay leaves
2 rosemary sprigs
One 14-ounce can whole plum tomatoes, coarsely chopped, juices reserved
In a medium enameled cast-iron casserole, heat 1 tablespoon of the olive oil until shimmering. Season the pork with salt and pepper. Add half of the pork to the casserole and cook over moderately high heat until browned on 2 sides, about 6 minutes. Transfer the pork to a bowl. Repeat with 1 tablespoon of the olive oil and the remaining pork.
Add the garlic, onion and ground fennel to the casserole and cook over moderately low heat, stirring occasionally, until the onion is softened, about 10 minutes. Add the tomato paste and cook over moderate heat, stirring, until glossy, about 2 minutes. Add the wine and simmer for 2 minutes. Stir in the stock and bring to a boil. Return the pork to the casserole and add the carrots, olives, thyme, bay leaves, rosemary and the tomatoes with their juices. Cover tightly and simmer over low heat, stirring a few times, until the pork is tender, about 2 1/2 hours. Discard the herb sprigs and bay leaves. Season the stew with salt and pepper and serve.
The stew can be refrigerated for up to 3 days. Reheat gently.