Throwdown Cuban Sandwich with Homemade Pickles

  • Yield : 8 to 10 servings
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  • 1 (4 to 5 pound) bone-in pork shoulder, excess fat trimmed
  • Kosher salt and freshly ground black pepper
  • 2 teaspoons ground cumin
  • Canola oil
  • 3 cups chicken stock
  • 1 cup fresh orange juice
  • 1/2 cup fresh lime juice
  • 2 tablespoons aged sherry vinegar
  • 1 head garlic, cloves removed and peeled
  • 2 medium Spanish onions, peeled and coarsely chopped
  • 2 bay leaves
  • Clover Honey
  • Handfull fresh oregano, stems with leaves
  • 3 Kirby cucumbers, sliced into 1/8-inch thick slices
  • 2 cups plus 2 tablespoons distilled white vinegar
  • 3/4 cup packed coarsely chopped fresh dill
  • 2-3 tablespoons sugar
  • 2 garlic cloves, coarsely chopped
  • 2 teaspoons kosher salt
  • 3/4 teaspoon dill seeds
  • 1/2 teaspoon whole mustard seeds
  • 1/2 teaspoon coriander seeds
  • 1 cup prepared mayonnaise
  • 3 tablespoons Dijon mustard
  • 5 cloves roasted garlic, pureed
  • Salt and freshly ground black pepper
  • 8 to 10 Cuban breads, sliced 3/4 of way through
  • Roasted Garlic-Dijon Aioli
  • Shredded pork
  • Homemade Pickles
  • 1 pound thinly sliced Swiss cheese
  • 1 pound thinly sliced good-quality ham


Step 1

Pork: Preheat oven to 350 degrees F. Season the pork with salt, pepper and cumin. Heat a few tablespoons of oil in a large Dutch oven until it begins to shimmer. Add the pork and cook until golden brown on all sides.

Step 2

Add the stock, juices, vinegar, garlic, onions, bay leaves and oregano, bring to a simmer, cover and transfer to the oven. Braise until fork tender (between 180 and 190 degrees F), about 1 1/2 hour to 2 hours. Remove from the oven, transfer pork to a platter and let rest 15 minutes before slicing or shredding. 

Step 3

Strain the braising liquid into a medium pan, bring to a boil and let reduced slightly, adding honey and salt and pepper if needed. Toss some of the braising liquid with the shredded pork to moisten.

Step 4

Homemade Pickles: Put the sliced cucumber in a medium bowl (which has a fitted lid). 

Step 5

Combine 1 cup of water, the vinegar, dill, sugar, garlic, salt, dill, mustard and coriander seeds in a small saucepan over high heat and bring to a boil. Cook until the sugar and salt is dissolved. Remove from the heat and taste for tartness, add more sugar if too sour and let cool to room temperature. 

Step 6

Pour the cooled liquid over the cucumbers, cover and refrigerate for at least 4 hours and up to 48 hours, stirring the mixture at least once.

Step 7

Roasted Garlic-Dijon Aioli: Whisk together mayonnaise, mustard and garlic and season with salt and pepper. Cover and refrigerate for at least 30 minutes before using to allow the flavors to meld.

Step 8

For Sandwiches: Spread both cut sides of the bread with a tablespoon or so of aioli. Add the pork, a few slices ham, and a generous layer of pickles. Top with a few slices cheese.

Step 9

Press the sandwiches in a hot panini grill until outside is toasty and cheese is melted.

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