1. In a small bowl, whisk together the orange and lime juices, oregano, cumin, kosher salt, red pepper flakes, and black pepper. Reserve 3 tablespoons of marinade in a separate bowl.
2. Put your pork tenderloin in a large Ziplock food storage bag and pour in the remaining marinade. Seal the bag, removing as much air as you as possibly can, and refrigerate for 1 hour.
3. Place and ovenproof skillet in the oven, then preheat the oven to 450 F. Once pre-heated, carefully remove the skillet from the oven wearing mitts, and add the vegetable oil, swirling to coat the bottom of the pan. Add the tenderloin to the skillet and return it to the oven. Roast for 10 minutes. Turn the tenderloin over. Reduce the oven temperature to 400 F and roast the pork for 10 minutes more (a total of 20 minutes).
4. Transfer the pork to a cutting board, cover loosely with aluminum foil, and let rest for a full 10 minutes to allow the juices to redistribute. Slice the tenderloin crosswise as thinly as you possibly can.
5. Now, it’s time to build your killer Cubans. Slice the sandwich rolls in half. To assemble each sandwich: spread both halves of the roll with 1-tablespoon mustard. Add 3 pickle slices to the bottom half, top with sliced pork, and drizzle with about 2 teaspoons of the reserved marinade. Add a slice of ham and cheese, and close the sandwich with the top of the roll. Brush the sandwich all over with ½ tablespoon olive oil.
6. Heat a large skillet over medium heat. When hot, add 1 or 2 sandwiches to the pan and place another heavy skillet (or any other heavy pan) on top. Cook for 3-4 minutes per side until the outside is golden brown and the cheese has melted. Repeat with the remaining sandwiches.
7. Slice the sandwich in half and serve immediately.
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