The Secret to Making a Perfect Cuban Sandwich

Courtesy of Andrews McMeel Publishing

One of the great sandwich mysteries, there's no actual documentation that proves whether or not the first Cuban sandwich was actually enjoyed in Cuba, or if a Cuban immigrant living in Florida during the early 20th century slapped together some ham, roasted pork, swiss cheese, and pickles, and the name just stuck. Some say the sandwich was something that was brought over to America, while others might claim that the Cuban sandwich as we know it today is really a product of the Sunshine State.

Whatever its true origin, the Cuban sandwich is delicious and that can't be denied. It is possibly one of the greatest types of sandwiches known to man, yet Kevin Gillespie, chef and author of the new cookbook Pure Pork Awesomeness: Totally Cookable Recipes from Around the Worldsays that he's had very few truly memorable Cubans, pointing out that the ones he's had "always seem dry."

DENVER, CO. 04/19/2007 -- Poppies, 2334 S. Colorado Blvd., French dip sandwich (Denver Post Staff Photo Brian Brainerd) (Photo By Brian Brainerd/The Denver Post via Getty Images)

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For his version, Gillespie uses soft, sweet challah bread rather than the traditional baguette-style bread, saying, "When you toast it, the sandwich still gets crispy on the outside, but the bread stays soft and moist inside." The challah gives the sandwich less crunch and soaks up more flavor, but the real secret comes in the mayo-based sauce that makes this version of the classic Cuban the one you might want to start making from now on. 

Kevin Gillespie's "Really Good Cuban Sandwich" 


  • 1¼ cups Duke’s mayonnaise
  • 1 large orange, for juicing
  • 1 lime, for juicing
  • 5 cloves garlic, mashed to a paste, about 4 teaspoons
  • 1 tablespoon toasted and finely ground cumin seeds
  • 2 teaspoons kosher salt
  • 1 bunch cilantro, leaves only, about 1 cup
  • 4 Cuban-style sandwich loaves, or 1 loaf brioche or challah bread, cut into eight ¾-inch thick slices (see headnote)
  • 2 teaspoons yellow mustard
  • 1 cup grated Gouda cheese (could be any kind of rich, easy-melting cow’s milk cheese)
  • 1 cup grated Gruyère cheese
  • 4 ounces thick-sliced deli ham
  • 10 ounces Slow-Cooked Pork
  • Barbacoa, sliced (see below)
  • Dill pickle slices, preferably flat, thinly sliced cucumber dill pickles


  1. In a blender, combine the mayonnaise, ½ cup orange juice, 1 tablespoon lime juice, garlic, cumin, and salt until smooth. Add the cilantro and blend until smooth and creamy, about 30 seconds.
  2. The order of assembly is important here! Spread the bottom slice of bread with mustard and sprinkle with the Gouda. Build the rest of the sandwich on the top slice of bread, starting with the Gruyère, followed by a slice of ham and the Barbacoa. Place a liberal layer of pickles over the pork, and top that with a full-on slathering of the cilantro mayonnaise. Flip the bottom up onto the top and press down firmly to compact.
  3. Heat a panini press to medium and coat lightly with nonstick spray or a brush of grapeseed or canola oil. You really want a nice, slow melt and toast. Place the sandwiches on the press, top side down, and close the top. Cook for 3 minutes, or until the bread is toasty and golden brown and the cheese starts melting. Alternatively, if you’re using a griddle, heat to medium and coat the pan lightly with nonstick spray or a brush of oil. You do not want a smoking-hot griddle here, or it will char the bread. Place the sandwiches on the griddle, top side down, and place a baking sheet on top of the sandwiches and then place some heavy weights on top to compress the sandwiches. Cook for 3 minutes, or until the bottom surface of the bread is golden brown and you start to see the cheese melting. Remove the baking sheet from the sandwiches, brush the top of the bread lightly with oil, then flip. Replace the baking sheet and weights on top and continue cooking until the sandwiches are golden brown and crispy and you can see the rest of the cheese melting, another 2 to 3 minutes. Remove the sandwiches, flip over, and cut in half on the diagonal. Serve the sandwiches with the remaining cilantro mayonnaise for dipping.

Slow-cooked pork barbacoa


  • 2 tablespoons kosher salt
  • 1 tablespoon ancho chili powder (or other single chili powder, not a blend)
  • ½ teaspoon ground cinnamon
  • ¼ teaspoon ground cloves
  • 5 pounds bone-in pork shoulder
  • 1 onion, quartered
  • 10 cloves garlic, peeled
  • 3 dried bay leaves


  1. Adjust the rack in the oven to a lower level so the roast will easily slide in.
  2. Heat the oven to 350°F.
  3. In a small bowl, combine the salt, chili powder, cinnamon, and cloves. Pat the pork dry and generously season all over with the salt mixture. Cut a large piece (about 24 inches) of heavy-duty foil and place in a roasting pan. Add the roast, onions, garlic, and bay leaves and wrap everything up tightly in the foil. Roast for 3½ hours.
  4. Remove from the oven and let rest, still wrapped in the foil, for 30 minutes.
  5. The foil will keep all the moisture and flavors in the packet and the shoulder will braise as it cools, creating very tender and juicy meat. Discard the onion, garlic, and bay leaves before shredding the meat.

 Good to Know

  • Instead of Boston butt, you could use the picnic part of the shoulder. Or use the whole shoulder if you have one. Just trim the fat down to ¹⁄8 inch or so.
  • For a simple family meal, just serve the shredded meat in corn tortillas with rice and beans and whatever toppings you like—chopped onion, grated cheese, a squeeze of lime.

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