Madeiran Pork with Wine and Garlic

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Ingredients

5 lbs. boneless pork shoulder, trimmed and cut into 1- to 1½-inch chunks
2 cups dry white wine
1 cup cider vinegar
10 bay leaves
6 medium garlic cloves, smashed and peeled
1 Tbsp. dried oregano
1 tsp. red pepper flakes
6 whole cloves (optional)
Kosher salt and ground black pepper
1 cup Madeira wine
¼ cup minced fresh oregano

Directions

  1. In a large Dutch oven, stir together the pork, wine, vinegar, bay, garlic, dried oregano, pepper flakes, cloves (if using) and 1 teaspoon each salt and pepper. Cover and refrigerate for at least 1 hour or for up to 48 hours.
  2. When you are ready to cook the pork, heat the oven to 325°F with a rack in the lower-middle position. Set the pot, uncovered, over medium-high and bring to a simmer, stirring occasionally. Re-cover, transfer to the oven and cook until a skewer inserted into the pork meets just a little resistance, about 1½ hours, stirring once about halfway through.
  3. Set a wire rack in a rimmed baking sheet. Using a slotted spoon, transfer the pork and garlic to the rack, removing and discarding the bay and cloves (if used); set aside. Tilt the pot to pool the cooking liquid to one side, then use a wide spoon to skim off as much fat as possible; reserve the fat. Or use a fat separator.
  4. Add the Madeira to the pot, bring to a boil over medium-high and cook, stirring occasionally, until the mixture has reduced to about 1 cup, 15 to 20 minutes; set aside. (We ended up with a LOT of liquid, so it took twice as long to reduce.) Remove and discard any large bits of fat on the exterior of the pieces of pork.
  5. In a 12-inch nonstick skillet over medium-high, heat 2 tablespoons of the reserved pork fat until barely smoking. Add the pork and cook, stirring every 2 to 3 minutes, until well browned on all sides, 5 to 7 minutes.
  6. Remove the skillet from the heat and add the reduced cooking liquid. Return to medium-high and continue to cook, stirring occasionally, until the liquid has reduced and the pork is lightly glazed and begins to sizzle, 3 to 5 minutes.
  7. Taste and season with salt and black pepper, then stir in the fresh oregano. Transfer to a serving dish.

Source

“Portuguese Classics,” Christopher Kimball's Mile Street, Season 5, Episode 4, October 1, 2021