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Cuban Picadillo
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Makes 4 - 6 Sandwiches

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A Cuban sandwich is a layered sandwich of ham, mojo-roasted pork, Swiss cheese, dill pickles, and mustard on pressed Cuban bread—bread baked in long loafs with a crisp exterior, a soft interior, and a palmetto leaf on top. Although the history of the sandwich is debated (check out our stories for more!), the politics and economics affecting its origin are undeniable. Some suggest that the predecessor to the Cuban was created by the indigenous Taíno tribe, who sandwiched cracker-like Cassava bread around fish; Spanish influence on the island transitioned the sandwich to one of bread and pork. Cuban cigar manufacturing moved first to Key West and then to Tampa, Florida in the late 1800s. The first written indication of a “Cuban sandwich” was recorded in cafes frequented by cigar-factory workers in Ybor City, Tampa, around 1900, although the sandwich was popularized in Miami, Florida after the Cuban Revolution led to an influx of immigrants to the United States. In Tampa, Cuban sandwiches include Genoa salami, which some attribute the influence of the Italians working alongside Cubans in Ybor City’s cigar factories.
Learn more about the politics of the Cuban Sandwich from The Politics of Cuisine on Instagram.
There are a million recipes for Cuban Sandwiches. This one is from here.

Ingredients
1 pound boneless pork shoulder
Kosher salt and freshly ground black pepper
1 tablespoon ground cumin
1 tablespoon dried oregano
2 tablespoons extra-virgin olive oil
4 cloves garlic, peeled and gently smashed with the side of your knife
1/4 teaspoon dried red chili flakes
1 medium onion, sliced
1 cup fresh orange juice
1 lime, juiced
1 cup low-sodium chicken broth
2 bay leaves
1 long Cuban bread roll
3 tablespoons Dijon mustard
8 thin slices Swiss cheese
1 cup bread and butter pickles
8 thin slices deli ham
Olive oil

Directions
Begin by braising the pork shoulder. Tie the shoulder in 4 places with kitchen twine so it will hold its shape while being cooked or ask your butcher to do this for you. Season the pork with salt, pepper, cumin and oregano. Set the base of a pressure cooker over low-medium heat and add a 2 count of olive oil.
Add garlic and chili flakes and as the oil heats up it will become fragrant and infuse the oil. Add the pork. Add onions around the pork and brown slightly before adding orange juice, lime juice, stock and bay leaves.
Secure the lid of the pressure cooker and cook for 20 to 25 minutes depending on the size of your pressure cooker. The pork should be tender when done. When done allow to cool in juices before removing twine and slicing.
To prepare Cuban sandwiches, split bread in half then layer the sandwich with mustard, cheese, pickles, ham, pork then cheese again (the cheese glues everything together). Season with salt and pepper in between the ham and pork layers. (Optional: drizzle a little of the pork braising liquid over the meat as well).
To cook, heat a large cast iron skillet or grill pan over medium heat and lightly coat with olive oil. Place the sandwiches on the skillet and top with another heavy skillet and a couple of heavy weights (bricks, or cans of tomatoes work well). Press down firmly and cook for 5 to 7 minutes per side until the sandwich has compressed to about a third of its original size and the bread is super-crispy. Serve with beans, rice and plantain chips.

The Cook:  Dave Ferguson Keywords: sandwich, Cuban, ham, pork, POC
Category: Sandwiches
Cookbooks: The Politics of Cuisine, All
Recipe #1280 was added on October 20, 2022 by deebeeeff and last updated on January 25, 2023.
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