Pulled Pork Sandwich with Homemade Coleslaw and Grilled Pineapple

Dripping with goodness, this pull-apart, mouth-watering sandwich is just sloppy and savory enough to wash away any worries. The juicy coleslaw and tart pineapple contrast beautifully with the tangy barbecue sauce and tender pork, creating a real masterpiece that will make taste buds pop. Grab a beer, sit back and enjoy.

Pork:

One 4-pound boneless pork shoulder roast

Kosher salt and freshly ground black pepper

2 tablespoons olive oil or canola oil

2 red onions, peeled and quartered

2 large carrots, peeled and cut into 1-inch chunks

3 celery sticks, cut into 1-inch chunks

1 whole garlic head, split in half horizontally

1 cup dry red wine

2 1/2 cups chicken stock

Small handful of fresh thyme sprigs

1 orange, quartered

1 bay leaf

1/2 teaspoon whole black peppercorns

Pineapple Barbecue Sauce:

1 tablespoon olive oil

1/3 cup finely chopped red onion

1 large garlic clove, finely chopped

1 cup ketchup

1 cup peeled cored finely diced pineapple

1/2 cup orange juice

1/4 cup low-sodium soy sauce

2 tablespoons chopped fresh cilantro

2 tablespoons chopped green onions

1/2 teaspoon ground cumin

1/2 teaspoon toasted sesame oil

Salt and freshly ground black pepper

Pineapple and Bread:

6 thin slices peeled pineapple, halved and cored

6 crusty rolls, halved horizontally

Coleslaw:

Homemade Coleslaw

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Directions

PREP TIME

HRS

MINS

COOKING TIME

HRS

MINS

Serves

Make-Ahead:

The pork can be braised 1 day ahead, cooled in its braising liquid, covered, and refrigerated. Rewarm the pork in its braising liquid, covered, over medium-low heat until it is hot. The barbecue sauce can be made 2 days ahead, cooled, covered, and refrigerated.

To cook the pork:

Preheat the oven to 140°C.

Sprinkle the pork shoulder all over with kosher salt and freshly ground black pepper. Heat a heavy large wide pot over high heat until it is very hot. Add the oil, and then add the pork. Cook until the pork is golden brown on the bottom, about 5 minutes. Turn the pork and continue cooking until it is golden brown all over, about 10 minutes. Transfer the pork to a baking sheet and pour off all but 2 tablespoons of the oil from the pot.

Add the onions, carrots, celery, and garlic to the pot and cook until the onions are golden brown all over, about 5 minutes. Return the pork to the pot. Add the wine and simmer until it is reduced by half, stirring to scrape up the browned bits on the bottom of the pot, about 3 minutes. Add the stock, thyme, orange, bay leaf, and peppercorns. Bring the liquids to a simmer, then cover the pot and place it in the oven.

Cook in the oven until the pork is fork-tender, about 2 1/2 hours. Remove the pot from the oven. Let stand uncovered at room temperature for 30 minutes to cool slightly.

Transfer the pork to a baking dish and pull the meat apart with a fork and knife. Toss the shredded pork with some of the warm barbecue sauce. Cover with foil to keep warm.

To make the pineapple barbecue sauce:

In a medium saucepan, heat the oil over medium heat. Add the onion and sauté until tender and pale golden, about 4 minutes. Add the garlic and sauté until fragrant, about 30 seconds. Add the ketchup, pineapple, orange juice, soy sauce, cilantro, green onions, cumin, and sesame oil.

Cook uncovered over medium-low heat until the pineapple softens, the mixture thickens, and the flavors blend, stirring occasionally, about 15 minutes. Season the sauce to taste with salt and pepper.

To prepare the pineapple and bread:

Preheat a grill pan over medium-high heat. Grill the pineapple slices until they are heated through and soften slightly, about 2 minutes per side.

Meanwhile, grill the bread slices, cut side down, until lightly toasted.

To serve:

Spoon the coleslaw over the bread bottoms. Top each with the shredded pork then 2 half slices of pineapple. Spoon more barbecue sauce over and cover with the bread tops. Serve warm.