Slow-Braised Pork Shoulder with Lemon, Olives, and Fennel with Roasted Brussels Sprouts

Season the pork shoulder chunks generously with salt, pepper, and dried oregano. Heat olive oil in a large heavy-bottomed pot or Dutch oven over high heat. Sear the pork on all sides for about 8 minutes total until deeply browned, then remove and set aside.

Preheat the oven to 160°C. Trim the Brussels sprouts and halve them. Toss with olive oil, salt, and pepper on a baking sheet, spreading them out in a single layer cut-side down for even roasting.

Reduce heat to medium in the same pot used for searing. Sauté sliced fennel, diced onion, and minced garlic for 5 minutes until softened. Add white wine, scraping up browned bits from the bottom of the pot. Stir in chicken stock, Kalamata olives, anchovy fillets, thin lemon slices, and bay leaves. Return the pork to the pot and bring to a simmer.

Cover the pot with the pork and transfer it to the preheated 160°C oven to braise for 2.5 hours until the pork falls apart easily. Simultaneously, place the tray of Brussels sprouts in the same oven to roast for the last 45 minutes of the pork’s cooking time, shaking the tray halfway through to ensure even browning and crisp edges.

Remove the lid from the pork pot and increase the oven temperature to 190°C. Cook for an additional 15 minutes to reduce the braising liquid and brown the top of the pork. Check the Brussels sprouts; they should be golden and crispy on the edges—if not, leave them in for the full 15 minutes.

Discard the bay leaves from the pork. Serve the pork in shallow bowls with the braised fennel, olives, and lemon slices, ladling the rich braising liquid over the top. Garnish with fresh arugula and a drizzle of olive oil. Plate the roasted Brussels sprouts alongside.