Citrus-Braised Pork Roast with Fennel and Olives

This slow-braised pork shoulder is built on a simple combination of fennel, citrus, white wine, and garlic that cooks into a rich, flavorful sauce. The Dutch oven provides steady, even heat, allowing the pork to become fork-tender while the exposed top develops a beautifully browned crust. A fresh olive and fennel relish spooned over the finished roast adds brightness and contrast just before serving. Pair with roasted potatoes and a green salad.

Braised Pork:

1 (10-pound) bone-in pork shoulder

Kosher salt and freshly ground black pepper

1 tablespoon fennel seeds, lightly crushed

2 tablespoons olive oil

2 large fennel bulbs, cut into wedges, fronds reserved

2 large yellow onions, cut into wedges

2 whole heads garlic, halved crosswise

2 cups dry white wine

1–2 cups chicken broth

1 orange

2 bay leaves

Olive-Fennel Relish:

1 cup Castelvetrano olives, crushed

½ cup parsley, finely chopped

1 cup reserved fennel fronds, finely chopped

1 lemon

¼ cup extra-virgin olive oil

Freshly ground black pepper

Flaky sea salt

Pat the pork dry and season generously all over with Kosher salt, pepper, and the crushed fennel seeds. Let it stand at room temperature for 30 to 45 minutes.

Preheat oven to 325°F. 

Heat a large Dutch oven over medium-high heat and add the olive oil. Brown the pork on all sides, including the fat cap, about 2 to 3 minutes per side, then transfer to a platter.

Reduce the heat to medium. Add the fennel, onions, and garlic, cut side-down, and cook until the vegetables begin to soften and the garlic is lightly caramelized, about 8 to 10 minutes.

Meanwhile, zest and juice the orange.

Pour the wine into the Dutch oven and scrape up any browned bits from the bottom. Stir in the orange zest and juice and bay leaves.

Return the pork to the Dutch oven, fat-side up, then add enough chicken broth so the liquid comes about ⅔ of the way up the side of the pork. Bring the mixture to a simmer, then cover and transfer to the oven. Cook for 5–6 hours, until the pork is very tender and a skewer slides easily into the center. (There’s no need to turn the pork while cooking, the braiser will self-baste the pork to keep it moist and create a browned crust on top.) 

When you have about an hour remaining on your pork, prepare the relish. Combine the crushed olives, parsley, fennel fronds, zest and juice of the lemon, black pepper, and a pinch of flaky salt in a small bowl, then drizzle in olive oil. Stir to combine and let stand while the pork rests.

Remove the Dutch oven from the oven and let the pork rest for 20 minutes. Discard the bay leaves.

Spoon the olive-fennel relish generously over the pork just before serving. Serve directly from the Dutch oven with the braised fennel and pan juices.