Recipe courtesy of Cafe Habana

Cuban Sandwich

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  • Level: Intermediate
  • Total: 4 hr 12 min
  • Prep: 45 min
  • Inactive: 12 min
  • Cook: 3 hr 15 min
  • Yield: 6 servings
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1/2 cup mayonnaise

4 canned chipotle chiles in adobo

6 long sandwich rolls, split in half - French loaf style bread

6 thin slices Black Forest ham

12 thin slices imported Swiss cheese

2 kosher dill pickles, thinly sliced lengthwise

1 1/2 pounds Roast Pork, thinly sliced or shredded (about 3 cups), plus reserved pan juices, recipe follows

Kosher salt

Roast Pork:

1 (8-pound) pork shoulder, boned

1 1/2 tablespoons minced garlic

1 cup plus 2 tablespoons distilled white vinegar

3/4 cup fresh lime juice

1/4 cup fresh grapefruit juice

1/4 cup fresh orange juice

2 tablespoons dried oregano, crumbled

1 tablespoon freshly ground black pepper

2 teaspoons adobo-style seasoning

Kosher salt and freshly ground black pepper

1 large green bell pepper, coarsely chopped

1 medium onion, coarsely chopped


  1. In a mini food processor, combine the mayonnaise and chipotles and process until smooth. Spread the cut sides of the rolls with the chipotle mayonnaise. Assemble the sandwiches with the ham, cheese, pickles and roast pork. Top the meat with a spoonful of the pork pan juices and season with salt. Close the sandwiches and tuck in any overhanging filling.
  2. Using an electric sandwich grill press, grill the sandwiches in batches until crispy and hot.
  3. Alternately, preheat the oven to 325 degrees F. Set a large skillet or griddle over moderately low heat. Arrange the sandwiches on the griddle and cover with a large baking sheet weighed down with a heavy skillet. Cook the sandwiches, turning once, until they're crisp on the outside, about 6 minutes.
  4. Transfer the sandwiches to a baking sheet and bake until the cheese is melted, about 8 minutes. Cut the sandwiches in half and serve immediately; pass the remaining pan juices separately.

Roast Pork:

  1. Using a small, sharp knife, make 1-inch-long slashes in the skin of the pork shoulder, about 2 inches apart. Rub the garlic into the slashes and along the underside of the pork.
  2. In a large glass or ceramic bowl, combine the vinegar, lime juice, grapefruit juice, orange juice, oregano, pepper, adobo seasoning, and salt and pepper. Stir in the green pepper and onion, then add the pork, skin side up. Refrigerate overnight turning the meat once or twice. Bring to room temperature before cooking.
  3. Preheat the oven to 400 degrees F. Transfer the pork and its marinade to a roasting pan. Cover with foil and roast until very tender, about 3 hours. Let cool in the liquid. Transfer the pork to a cutting board and discard the skin and fat. Strain the pan juices into a glass measure and skim off the fat. Slice or shred the pork, as desired.

Cook’s Note

The pork can be refrigerated for up to 3 days.

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