Preheat oven to 325 °F (160 °C).

Season short ribs generously with salt and pepper.

In a heavy Dutch oven over medium‑high heat, warm olive oil. Sear ribs on all sides until deep brown. Remove and set aside.

Add leeks and prunes to the pot; sauté until prunes begin to caramelize.

Pour in red wine and vinegar, scraping up browned bits. Simmer for 3–5 minutes until reduced slightly.

Stir in olives, capers, caper brine, garlic, bay leaves, oregano, and brown sugar.

Nestle the ribs back into the sauce, bone‑side down. Cover and braise in oven for 2–2½ hours, or until meat is super tender.

Remove ribs and bay leaves. Strain sauce, return to stovetop, and whisk in butter until glossy. Reintroduce olives, leeks, capers, and remaining half of the prunes to warm through gently.

Plate ribs and spoon sauce over top. Serve with mashed potatoes, sweet potatoes, or roasted root vegetables.