- 1 cup dry red wine
- ¾ cup balsamic vinegar
- 1 tablespoon sugar
- ¼ cup olive oil, or more if needed
- One 4- to 5-pound boneless beef shoulder pot roast
- ¼ cup kosher salt
- ¼ cup freshly cracked black pepper
- 2 large red onions, peeled and diced small
- ¼ cup minced garlic
- 6 plum tomatoes, cored and diced small
- 1 cup dark raisins
- 2 lemons, peeled, cut into segments, seeded (see headnote)
- 1 to 2 cups beef stock
- Kosher salt and freshly cracked black pepper to taste
- 1 cup roughly chopped pitted black olives
- ¼ cup pine nuts, toasted in a 350°F oven until lightly browned, about 10 minutes
- 1 cup roughly chopped fresh basil or parsley
- ¼ cup extra virgin olive oil
- Kosher salt and freshly cracked black pepper to taste
- Preheat the oven to 300°F.
- In a medium bowl, combine the wine, vinegar, and sugar. Mix well to dissolve the sugar and set aside.
- In a 5-inch-deep Dutch oven or other large ovenproof pot with a lid, heat the oil over medium-high heat until very hot but not smoking. Dry the meat with paper towels, then rub it all over with the salt and pepper, pressing gently to make sure they adhere. Place the roast in the pot and brown it well on all sides, about 10 minutes total. When the meat is browned, transfer it to a platter and set it aside.
- Pour off the fat or add oil to the pot as needed so you have a total of about 2 tablespoons in the pot. Add the onions and cook, stirring occasionally, until translucent, 7 to 9 minutes. Add the garlic and cook, stirring, for 1 minute more.
- Return the meat to the pot and add the tomatoes, raisins, lemons, and wine-vinegar mixture. Add enough stock so that the liquid comes about one quarter of the way up the sides of the meat (the tomatoes will quickly give off more liquid). Bring to a simmer, scraping any browned bits from the bottom of the pot. Skim any scum off the surface. Cover, place in the oven, and cook until the meat is tender, 2 to 2½ hours. Begin checking for doneness after 2 hours. To check for doneness, plunge a fork straight down into the meat and try to pull the fork out. If the fork slides out easily, the meat is done; if the meat hangs on to the fork, give it more time.
- While the meat is cooking, make the relish: In a medium bowl, combine the olives, pine nuts, basil, olive oil, and salt and pepper and mix well.
- When the meat is done, remove it from the pot, cover it loosely with foil, and set aside. Skim the fat from the braising liquid and taste the liquid. If it needs more flavor, place the pot on the stove over medium-high heat and simmer to reduce the liquid. For a thicker sauce, reduce it until it coats the back of a spoon. Season to taste with salt and pepper.
- Cut the pot roast against the grain into thick slices, spoon some of the sauce over the top, and pass the remaining sauce and the relish separately for guests to sprinkle over the beef.