Pulled Pork Sandwich with Coleslaw


1 4-pound boneless pork shoulder roast
Kosher salt and freshly ground black pepper
2 Tbsp 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 c dry red wine
2 1/2 c chicken stock
Small handful of fresh thyme sprigs
1 orange quartered
1 bay leaf
1/2 tsp whole black peppercorns
Barbecue Sauce
6 thin slices peeled pineapple halved and cored
6 crusty rolls halved horizontally


Preheat the oven to 275°F. 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 bakingsheet 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.
Meanwhile 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.

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.