Makes 6 servings
Active time: 1 hr
Total time: 4 hr
INGREDIENTS

1/3 cup all-purpose flour

Salt

Freshly ground black pepper

5 pounds short ribs (not cross-cut flanken)

4 tablespoons olive oil, divided

2 medium red onions, cut into 1-inch pieces

2 carrots, cut into 1/2-inch pieces

1 celery rib, cut into 1/2-inch pieces

3 large garlic cloves, chopped

2 tablespoons chopped fresh rosemary

1 tablespoon fresh thyme leaves

2 cups full-bodied red wine, such as Côtes du Rhône or Bordeaux

2 cups low-sodium chicken broth

1 (15-ounce) can whole peeled tomatoes in juice

3/4 cup balsamic vinegar

2/3 cup (3 1/2 ounces) pitted kalamata olives, rinsed and patted dry

1 navel orange

EQUIPMENT

A wide 6- to 8-quart heavy pot with a tight-fitting lid (for an alternative, see Cooks’ Notes)

ACCOMPANIMENTS

Polenta, noodles, or potatoes

INSTRUCTIONS

Heat oven to 350°F with rack in lower third.
Stir together flour with 1 1/2 teaspoons salt and 1/2 teaspoon pepper in a bowl. Pat ribs dry and lightly dredge in flour mixture, knocking off excess.
Heat 2 tablespoons oil in a wide 6- to 8-quart heavy pot over medium-high heat until it shimmers. Brown ribs in 3 batches, about 8 minutes per batch. Transfer as browned to a platter. Discard fat from pot.
Cook onions, carrots, and celery in remaining 2 tablespoons oil with 1/2 teaspoon salt over medium heat, stirring occasionally, until just softened and beginning to brown, 8 to 10 minutes.
Add garlic and herbs and cook, stirring frequently, until garlic is softened and fragrant, 2 minutes.
Add wine and boil until reduced by half, about 8 minutes, then stir in broth, tomatoes with juice, and vinegar and bring to a simmer.
Return ribs to pot. Cover with the lid, then place in oven, and braise until ribs are fork-tender, 3 to 3 1/4 hours.
Transfer ribs with a slotted spoon to a bowl. Let cooking liquid stand briefly, then skim fat from top. Stir in olives. Adjust seasoning to taste, if necessary.
Return meat to pot. Grate zest from orange over top just before serving.
COOKS’ NOTES

Short ribs can be braised up to 3 days ahead. Once braised, bring to room temperature, uncovered, then keep chilled, covered.
Instead of a large heavy pot, you can use a 12-inch heavy skillet to brown the short ribs and cook the vegetables, transferring them as browned to a small nonreactive roasting pan. Deglaze the skillet with the wine, then pour it into the roasting pan with the remaining ingredients. Cover the pan tightly with heavy-duty foil (or a double layer of regular foil), then bring the liquid to a simmer, before transferring the pan to the oven.