Slow Roasted Cuban Style Pork Shoulder and The Payoff Cubano Sandwich

A good Cubano sandwich has been on our cooking checklist for some time now.  The other day I came across a whole bone-in, skin-on, pork shoulder and could not pass it up.  First up, roasted pork shoulder, black beans and rice, and caramelized onion compote.  Next up, the payoff Cubano.  It was a multi day, multi pork kind of experience.  After all, we are talking about a eight pound pork shoulder.  There will be a lot of pork eating for all.  

For the pork roast, plan to start the prep process at least one day ahead and the cooking process about 10 hours before eating.

One bone-in pork shoulder/butt, 7-8 pounds, skin on or off, but you want a nice layer of fat on top if the skin is taken off
2 cups orange juice
1 cup lime juice
2 small onions, thinly sliced
4 cloves garlic, finely chopped
2 teaspoons dried oregano
1 teaspoon ground cumin
2 dried bay leaves
2 tablespoons salt
½ teaspoon ground black pepper

Pierce the pork all over with a small thin knife to allow the marinade to penetrate into the pork.   Combine all ingredients and place in a large plastic zip log bag.  Place in refrigerator for at least one day and up to two days.

In the morning, take the pork out of the refrigerator and carefully remove it from the bag, making sure to keep the marinade in tact.  
Place the pork on a small piece of parchment paper on a rack set inside a roasting pan.  Let sit at room temp for at least 30 minutes.
Heat oven to 250f.
Strain the solids from the liquid of the marinade, reserving both.
Separate ½ cup of the marinade for the sauce and 1 cup for basting the pork.
Place the pork in the middle of the oven and roast for about 8-9 hours, or until tender, but not pull apart tender.  
Baste the pork periodically with the reserved marinade.
If the pork gets too brown on top, take a small piece of foil and cover the skin, but do not wrap up the pork entirely.  You don't want it to steam.
Take the pork out of the oven, pour pan drippings into a measuring cup and separate the fat from the juices.
Turn oven up to 450f. 
Let pork rest for at least 20 minutes and up to an hour.  Then place the pork back in the oven to crisp the skin.  You may skip this step if the pork does not have skin on it.

While the pork is resting, make the caramelized onion sauce.  
In a large skillet, sauté the onions, etc. from the marinate in a little olive oil over medium high heat.  Sauté until the onions are quite soft and caramelized.  Add the pan drippings and  the ½ cup of reserved marinade and bring to a boil.  Turn heat to medium and let simmer until the liquid is reduced by half.

For the first night's meal, I sliced the pork and served it with black beans and rice and the onion compote on the side.  Here's a good recipe for the rice at Goya's website.

My thoughts on the Cubano sandwich is that the bread is almost as important as the pork.  I am still in search of the perfect bun for it, but what I used worked out just fine. 
For the sandwich you'll need a good substantial, but not too soft and not too dense bun.  I used Seattle International Baking Company French Sandwich Roll.
For each sandwich:
few slices of the roast pork
few slices of good smoked ham
swiss cheese
long sliced dill pickles
caramelized onion (I used a little from the sauce from the previous night)
yellow mustard
aioli

Heat a skillet over medium high heat and quick fry the roast pork slices and smoked ham just long enough to warm them up and create a slight brown on the meat.
Assemble the sandwich, spreading the yellow mustard and aioli and each side of the bun. 
On the bottom side of the bun, put a piece of swiss cheese, then roast pork, pickles, caramelized onion, ham,  then another slice of swiss cheese.

Melt a few tablespoons of butter.  

To grill the sandwiches, you can use a panini press, waffle iron/griddle like I did, or two skillets, one to fry the sandwich and one to weigh the sandwich down.
Heat the griddle to medium high.  Brush with a little butter, lay the sandwich on top of the butter and then brush the top of the sandwich with more butter.  Lower the lid of the press/griddle and fry the sandwich until it is golden brown and the cheese has melted.  Adjust the heat as needed so not to burn the sandwich.  
If you are using two skillets, you'll have to flip the sandwich to fry the other side.

That was a lot of pork!  But we spread it out over the course of a few days, skipping a couple days in between.  I'm going to keep this in the files for a football party in the fall.
Cubanos for all!