4 large garlic cloves, divided
3 pounds 3- to 4-inch meaty bone-in beef short ribs
2 teaspoons kosher salt
½ teaspoon black pepper
tablespoons canola oil
1 medium yellow onion, chopped (about 2 cups)
1 (28-ounce) can whole peeled plum tomatoes with juices
1 cup dry red wine
1 cup water
10 (6-inch) oregano sprigs
1 tablespoon fennel seeds
1 tablespoon habanero hot sauce (such as Siete)
1 teaspoon ground allspice
1 teaspoon grated orange zest, plus 2 tablespoons fresh juice (from 1 orange), divided
1 (16-ounce) package pappardelle pasta
½ cup finely chopped fresh flat-leaf parsley
Preheat oven to 325°F. Using flat side of a chef's knife, smash 3 of the garlic cloves; set aside. Sprinkle beef evenly with salt and black pepper. Heat oil in a large Dutch oven over medium-high. Add beef; cook, turning occasionally, until deeply browned on all sides, 12 to 15 minutes. Transfer beef to a plate. Reserve 2 tablespoons drippings in Dutch oven. Add onion and smashed garlic to Dutch oven; cook over medium-high, stirring constantly, until fragrant, about 1 minute. Add tomatoes with juices, crushing tomatoes with your hands as you add them. Add wine, water, oregano, fennel seeds, hot sauce, and allspice; stir to combine. Nestle beef into sauce. Bring to a boil over high. Remove from heat and cover.
Transfer Dutch oven to preheated oven. Bake until meat is falling off the bone, 2 hours, 30 minutes to 3 hours. Remove from oven. Remove and discard bones and oregano sprigs. Skim fat from surface. Using 2 forks, shred beef in Dutch oven. Stir orange juice into ragù. The ragù can be cooled, covered, and refrigerated for up to 2 days. Reheat before continuing.
Cook pasta according to package directions; drain. While pasta cooks, finely grate remaining garlic clove. Stir together grated garlic, parsley, and orange zest in a small bowl for the gremolata. Divide cooked pasta evenly among 4 bowls. Top pasta evenly with ragù and gremolata.
