The Cowboy Cuban Sandwich

Howdy folks, and thanks for stopping by the website! The Cuban Sandwich is a diner favorite across the United States. I researched the origins of the Cuban and came up with a delicious recipe using leftover shredded Pork Carnitas, and of course, added a little cowboy zing to the sandwich with a sweet & spicy mustard.

The Origins of the Cuban Sandwich

Tampa and Miami, Florida have an ongoing debate about which city created the Cuban and who makes it better. I’m siding with Miami today – Tampa likes to layer up the salami on their Cuban sandwiches. I’m siding with Miami and the pork.

The reason the Cuban is grilled flat is because bricklayers in Miami needed a hearty sandwich to fuel them through a full day of hard work. The sandwich typically held two types of meat – usually thin-sliced ham and shredded pork. Traditionally, a pork shoulder would marinate in a citrus garlic sauce for about six to seven hours, and then slow roast until it was falling apart. This became the bulk of the sandwich.

These men were working all day in the hot sun, so they could not put mayonnaise on their sandwich or else it would spoil. That’s why the sandwiches always have mustard.

The bricklayers would take a hot brick and place it on top of the sandwich. This led to the bread being pressed flat like a panini, and the sandwich would be hot and melty by the time lunch rolled around. The end result was a hearty sandwich full of the flavors of the pork, citrus, mustard, and pickles.

Cuban Sandwich Made With Leftover Pork Carnitas

I happened to have some smoked pulled pork left over from this Pork Carnitas recipe. I’m going to heat this pork up and transform the pulled pork with some garlic and citrus. I squeezed the juice right out of a lime and an orange with a LOT of garlic – six cloves.

TIP: Add garlic in the last five minutes of cooking the shredded pork to prevent burning.

Other Pork Options: You can use a pork loin and slice it thin instead of shredding. You can cube up a pork chop or pork stop – whichever you prefer.

Assembling the Cuban Sandwich

Start by buttering both sides of the bread and grilling it. This doesn’t just add flavor, it also helps seal the bread so the mustard and pickle juice doesn’t make the bun soggy.

Tip: Heat up the thin-sliced deli ham before adding it to the sandwich. The cheese will melt easier.

You can use any mustard you like on this sandwich – and it must be mustard! I used the Sweet and Spicy Mustard by the Fresh Chile Company. The hatch chiles in the mustard are delicious!

Visit and use CODE: KENT15 for 15% off.

After the mustard, lay out the deli ham. The next layer: swiss. Top with the citrus garlic pulled pork and finish off with two big pickle slices.

We wrapped a hot brick in foil and pressed the sandwich down on both sides, getting good grill marks on either side of the bread and melting the cheese. The result is a delicious grilled Cuban sandwich that will fill a cowboy up, it will.

Kent Rollins Cowboy Cuban Sandwich grilled with a brick; sitting before the Fresh Chile Company Sweet and Spicy Mustard

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Cuban Sandwich – Cowboy Kent Rollins

Prep Time 5 minutes
Total Time 30 minutes
Servings 4


  • ¾ lb. shredded pork shoulder see note
  • Juice of 1 orange
  • Juice of 1 lime
  • 8 garlic cloves minced
  • 24 deli ham slices
  • 4 hoagie rolls
  • 1 stick butter melted
  • 8 Swiss cheese slices
  • Dill pickle slices for topping
  • Mustard for spreading yellow, Dijon, etc. See Note


  • Add the pork to a large cast iron skillet over medium-high heat. As it begins to warm, stir in the orange juice, lime juice, and garlic. Cook for about 5 minutes, or until the pork becomes slightly crisped and brown, stirring occasionally. Set aside to keep warm.
  • Warm the ham, over the grill or in a separate skillet over medium heat.
  • Butter the insides of the hoagie rolls and place on the grill or in a skillet to toast.
  • To assemble the sandwiches: place 6 slices of ham on the bread, followed by a generous heaping of the shredded pork, 2 Swiss cheese slices, and pickles. Spread the underside of the top bun with mustard and top the sandwich. Repeat with the remaining ingredients.
  • Generously butter the top sides of the buns. Place the sandwiches on a hot grill, top side down, and place a brick wrapped in tinfoil, skillet or press on top of the sandwich to flatten slightly. Cook until toasted.
  • Remove the brick or skillet and generously butter the bread. Flip over and place the skillet/brick back on the sandwich and cook until toasted.
  • Remove from the heat and serve warm.


See our Pork Carnitas for pork recipe 
We used Fresh Chile Co. Sweet and Spicy Mustard- it’s amazing! 15% of with code: Kent15
Tried this recipe?Let us know how it was!