This dish is incredibly simple to create and is a classic addition to any Juneteenth and weeknight repertoire. The five pounds of bone-in short ribs are braised for three hours until the meat is tender and falling off the bone.
Technical tip: Buy thick cuts as the meat will shrink a lot.
Preheat the oven to 300F.
Generously season the short ribs with the flour, salt and pepper. Heat a large Dutch oven or heavy-bottomed pot over high heat and add the oil. Add the short ribs in batches and brown on all sides, about 3 minutes on each side. Transfer the ribs to a plate.
Meanwhile, add carrots, celery and onion to a food processor and pulse until vegetables are almost pureed, about 30 seconds.
Reduce heat under saucepan to medium-high, add mashed vegetables and sauté, stirring often, until vegetables are softened, about 5 minutes. Add the tomato paste, Italian seasoning and a pinch of flour. Cook, stirring constantly, until the tomato paste blackens slightly, about 3 minutes. Slowly pour in the wine, whisking; whisk until smooth and combined. Add the sugar to the wine. Bring to a boil, reduce heat to low, and cook until wine is reduced by half, 10 to 15 minutes.
Stir in the broth, garlic and bay leaves, bring to a boil, turn off the heat and return the ribs to the pan. Cover, transfer to oven and cook until ribs are tender, about 3 hours.