Cuban Sandwich

Total Time:
2 hr 25 min
Prep:
20 min
Inactive:
1 hr 10 min
Cook:
55 min

Yield:
4 servings
Level:
Intermediate

Ingredients
  • Pickles:
  • 3 cups white wine vinegar
  • 1/4 cup chopped fresh dill
  • 1/4 cup sugar
  • 2 tablespoons kosher salt
  • 1 teaspoon coriander seeds
  • 1 teaspoon mustard seeds
  • 2 kirby cucumbers, sliced 1/4-inch thick
  • Sour Orange Glaze:
  • 2 cups freshly squeezed orange juice
  • 1/2 cup freshly squeezed lime juice
  • 2 tablespoons clover honey
  • 1 tablespoon white wine vinegar
  • Kosher salt and freshly ground black pepper
  • Pork:
  • 1 1/2 pounds pork tenderloin, trimmed
  • Kosher salt and freshly ground black pepper
  • 1/4 cup steak rub, such as Bobby Flay's Steak Rub
  • 3 tablespoons canola oil
  • Garlic Mayonnaise:
  • 3/4 cup mayonnaise
  • 2 heaping tablespoons whole-grain mustard
  • 2 teaspoons finely chopped fresh oregano
  • 2 cloves garlic, chopped to a paste
  • Kosher salt and freshly ground black pepper
  • Serrano Ham:
  • 1 cup canola oil
  • 8 thin slices Serrano ham
  • To serve:
  • 4 Cuban buns, split
  • 16 thin slices Swiss cheese
  • 1 stick (8 tablespoons) unsalted butter, softened
Directions
  • For the pickles: Combine the vinegar, dill, sugar, salt, coriander and mustard in a medium saucepan. Bring to a boil over high heat and cook until the sugar and salt are dissolved. Remove from the heat and let cool for 15 minutes. Put the cucumbers in a medium bowl, pour the pickling liquid over, cover the bowl and refrigerate for at least 30 minutes and up to 24 hours.

  • For the sour orange glaze: Combine the orange juice and lime juice in a small nonreactive saucepan over high heat and cook until reduced to 1/2 cup, about 20 minutes. Whisk in the honey and vinegar and season with salt and pepper. Let cool slightly.

  • For the pork: Preheat the oven to 425 degrees F. Season the pork with salt and pepper and rub with the steak rub. Let sit for 15 minutes at room temperature.

  • Heat the oil over high heat in a cast-iron pan or oven-proof skillet until it begins to shimmer. Add the pork and cook until a crust has formed on all sides, about 2 minutes per side. Brush liberally with the sour orange glaze and transfer the pan to the oven. Brush with the glaze every few minutes, and cook until an instant-read thermometer inserted into the center of the pork registers 145 degrees F, about 10 minutes. Remove the pork to a cutting board and let rest for 10 minutes before slicing. Slice the pork thinly.

  • For the garlic mayonnaise: Combine the mayonnaise, mustard, oregano, garlic, salt and pepper to taste in a small bowl. Whisk together and let sit at room temperature for at least 15 minutes to allow the flavors to meld.

  • For the serrano ham: Heat the oil in a small saucepan until it reaches 350 degrees F. Add the ham one slice at a time and cook until crisp, about 30 seconds. Drain on a plate lined with paper towels.

  • To serve: Spread the top and bottom of each bun with the garlic mayonnaise and top each piece with 2 slices of cheese. Put some pickles on the bottom piece of bun. Top with 4 to 5 slices of the pork and 2 slices of the fried ham. Combine the tops and bottoms to make the sandwiches.

  • Brush the outsides of the buns with the butter. Heat a cast-iron pan over low heat. Put 2 sandwiches in at a time, top-sides down, and press with a brick wrapped in foil, or put foil over the top of the sandwiches and weigh them down with another heavy cast-iron pan. Cook until the bread is crispy, then flip over and continue cooking until the bottom is crispy and the cheese has melted, 6 to 8 minutes total. Slice in half and eat.


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