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Grilled Cheese with Roast Pork, Confit Tomatoes, and Balsamic Mayo

Yield: 8 sandwiches

  • 2 lbs. boneless pork shoulder
  • 2 tsp. salt
  • 1 tsp. paprika
  • 2 tsp. freshly ground black pepper
  • 2 tsp. sugar
  • 10 medium Roma tomatoes, or a basket of cherry tomatoes
  • 4 cloves of garlic, peeled and crushed
  • 1 sprig fresh thyme
  • 2 cups olive oil
  • 1 tsp. sea salt
  • 1 cup balsamic vinegar
  • 3 Tbs. mayonnaise
  • 1 ½ lbs. of your favorite melting cheese(s), sliced in ¼ inch pieces
  • 16 slices thick, artisan bread
  • Butter, enough to coat bread

Pork Roast (can be made up to three days ahead)

Preheat oven to 250°F. Combine the salt, paprika, pepper, and sugar. Coat the pork roast in the spice rub.  Roast until the internal temp reaches 150°F. Let the roast rest for at least 30 minutes, tented in foil, before cutting, or refrigerate until needed.

Confit tomatoes

Preheat the oven to 250°F (tomatoes can share the oven with the pork). Slice the tomatoes in half and then cut each half into three wedges. Place the tomatoes in an oven-safe container, just big enough to hold them. Add the garlic, thyme, olive oil, and ½ teaspoon salt. Mix well. Roast the mixture for 1 ½ hours, or until the tomatoes are deep red and starting to brown a little on top. Remove from the oven and set aside. Store in their oil in the refrigerator, bring to room temperature before using. The oil is great in a salad dressing once you’ve used up the tomatoes.

Balsamic reduction*

Pour balsamic into a small saucepan. Bring to a boil and then reduce to a simmer. Allow the vinegar to reduce by ½. Remove from the heat and let it cool a little before using. Pour 1/4 cup of reduction into a small bowl. Add mayonnaise and mix thoroughly. Add more balsamic as needed, to taste.

*Another way to make the reduction if you happen to have a day or two extra: Just pour balsamic in a large flat container, and leave it out in a warm place. It will reduce on its own, if you’re patient!

Assemble sandwich

Spread balsamic mayo on the “inside” of both slices of bread. Lay the bottom slice down. Put a ¼ - ½ inch slice of pork roast on the bread (if you’ve made the pork ahead, heat it on the griddle for a minute on both sides before using). Add ¼ cup of confit tomatoes and garlic (be sure to discard the thyme). Lay slices of cheese across the top of the tomatoes. Place the prepared top layer of bread over it all. Melt butter in a cast iron or non-stick pan over medium heat. Grill the sandwich on both sides until golden brown, with a lid or upside-down cake pan to hold in heat. If the cheese isn’t melted, sprinkle a teaspoon of water in the pan and cover to steam. Remove from the pan, slice and plate. Drizzle balsamic reduction over the top of the sandwich and serve.

The photos below were taken at Cook! Programs dinner class. The kids made tomato soup, these yummy sandwiches, a delicious fennel and cucumber salad, and pavlova with berries for dessert. You can tell they were happy, as were their parents who got to come eat too!