Cuban Sandwiches

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  • Total: 33 min
  • Prep: 8 min
  • Cook: 25 min
  • Yield: 4 main-course servings.
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Two 15-inch-long soft French or Italian bread loaves

1/4 cup yellow mustard

4 ounces thinly sliced boiled ham

8 lengthwise slices dill pickle (from about 2 pickles)

2 cups pulled SLOW-ROASTED PORK, recipe follows

4 ounces thinly sliced Swiss cheese

2 tablespoons unsalted butter


2 heaping tablespoons black peppercorns

25 cloves garlic, (about 2 heads) peeled

10 whole cloves

3/4 cup vegetable oil

1 bone-in pork shoulder, (about 7 pounds)

Kosher salt, as needed

White distilled vinegar, as needed


  1. Slice off about 1-inch from the ends of the bread loaves and discard or save for breadcrumbs. Cut each loaf in half to make 4 rectangular loaves. Split each loaf in half lengthwise. Spread the inside of the bread with 1/2-tablespoon mustard. On each of the bottom halves of bread layer 1/4 of the ham, pickle slices cut to fit evenly on top of the meat, 1/4 of the pork, and top with 1/4 of the cheese. Cover with the top halves of bread and, using your hands, press the sandwiches together. 
  2. Place a baking sheet in the oven and preheat to 250 degrees F. Melt 1 tablespoon butter in a large cast-iron skillet over medium-low heat. Place 2 sandwiches in the skillet and top with another cast-iron skillet to weigh them down. Turn the sandwiches and weigh them down again. Cook the sandwiches until golden brown and hot, about 6 minutes per side. Transfer to the oven to keep warm. Repeat with the remaining sandwiches and butter. Cut the sandwiches in half crosswise and serve immediately.


  1. Preheat the oven to 275 degrees F. 
  2. In a food processor, combine the peppercorns, garlic, and cloves and puree. While the motor is running, drizzle in the oil until a paste is formed. Using a rubber spatula, scrap the garlic paste into a small bowl. 
  3. Place the pork butt on a work surface and season all over generously with salt. Rub all over with the garlic paste. Place in an oven-safe roasting bag and close with a twist tie. Place in a large roasting pan, and cook until tender, about 5 hours.