This is exactly the right kind of savory, warming dish to bring to a friend who is feeling unwell. Or at least, that’s why I made it last winter. It was for Josh, who was just back home from the hospital after being hit by a car while riding his bike. His wrist was smashed to bits, and he would need a year of surgeries before he fully recovered. But more important, his spirit was shaken. He vacillated between feelings of terror (he really could have died), anger (why was that *&$%&* car service driver speeding up Eighth Avenue anyway?), intense gratitude (for being alive), and deep love for his family (his wife, Bryony, and toddler daughter, Willa). Josh needed many things and nothing from his friends in those fragile, post-accident days, including excellent, soul-sustaining meals. That was right up my alley. Naturally, I wanted to make him something special, but didn’t know what. So I wandered the farmers’ market stalls that morning, looking for inspiration, which unveiled itself to me in the form of a small chunk of pork shoulder. Offering various shoulders to Josh and family - to cry on, to eatseemed apropos for this particular situation, so I snapped it right up. With a pork shoulder in the bag, a cook has options. I could have roasted it surrounded by the season’s last root vegetables. But by this point in the season, I was tiring of root vegetables. And a braise is always easier to transport and reheat than a roast. For the seasonings, I wanted to simmer up something comforting but different, something vaguely exotic that would taste of sunny, faraway places where no one ever drove SUVs at top speed down residential streets. I doubt this place exists, but if it does, I’m sure they use plenty of dry red wine and sweet spices in their braises, along with anchovies for complexity, and tart olives and those canned plum tomatoes I had in the cupboard as a bright contrast. I cooked it carefully and brought it over to Josh's house with some freshly made polenta and a chilled bottle of Champagne. Because this dinner was a celebration - of luck, pork, dedicated bike lanes, and most important, eating good food with dear friends.
2pounds pork shoulder (also called pork butt), cut into 2-inch chunks
Kosher salt and freshly ground black pepper, for seasoning
2tablespoons olive oil
2large leeks, white and light green parts only, sliced
5cloves garlic, smashed and peeled
128-ounce can plum tomatoes
1cup dry red wine
12-inch piece cinnamon stick
2 bay leaves
2 rosemary sprigs
2/3cup pitted and roughly chopped green olives
Cooked polenta, for serving
Preheat the oven to 300°F. Season the pork shoulder generously with salt and pepper. In a Dutch oven over medium-high heat, warm the olive oil and sear the pork, turning, until it is well browned all over, about 10 minutes. Transfer the pork to a plate.
Add the leeks and garlic to the Dutch oven and brown, stirring, 3 to 5 minutes.
Return the pork to the Dutch oven and add the tomatoes, wine, anchovies, cinnamon stick, bay leaves, and rosemary. Cover the Dutch oven and place it in the oven. Cook for 1 1/2 to 2 hours, turning the pork twice during cooking (once after 45 minutes and again after an hour and a half).
Raise the temperature to 425°F. Uncover the Dutch oven and add the olives. Continue cooking, uncovered, until the liquid is reduced and the meat is very tender, about 20 minutes more. If you have made this ahead of time, let it cool so the fat has a chance to rise to the surface, then spoon it off if you like (I usually don't bother). If you've made it the day before, chilling hardens the fat and makes it really easy to spoon off. Reheat if necessary and serve over polenta.