Cut the Beef Chuck into 1½–2 inch cubes. In a large bowl combine the Dry Red Wine, Red Wine Vinegar, smashed cloves of Garlic, a cinnamon stick (Cinnamon), a few Allspice Berries, 1–2 Bay Leaf and a teaspoon of Black Peppercorns. Add the beef, cover, and refrigerate to marinate for at least 4 hours or overnight for best flavor.
Remove the beef from the marinade, reserving the liquid and whole spices. Pat the meat dry and season generously with Fine Salt and freshly ground Black Pepper.
Heat a few tablespoons of Extra-Virgin Olive Oil in a heavy, ovenproof pot or Dutch oven over medium-high heat. Working in batches, brown the beef on all sides until well caramelized; transfer browned pieces to a plate and set aside.
Add the Small Pearl Onions to the pot and cook, stirring, until they begin to brown and soften. Add a couple of crushed garlic cloves (from the reserved garlic) and cook 30–60 seconds until fragrant.
Stir in the Tomato Paste and cook 1–2 minutes to deepen its flavor. Then add the Canned Crushed Tomatoes, the reserved marinade (strain out large solids if you prefer), the Beef Stock to just cover the meat, a tablespoon of Sugar, and a few whole Cloves. Return the browned beef to the pot.
Bring the stew to a gentle simmer, then reduce the heat to low, cover partially, and cook gently for 2–3 hours until the meat is fork-tender and the flavors are well melded. Stir occasionally and skim any excess fat.
If the sauce is too thin at the end, uncover for the last 20–30 minutes to reduce and concentrate flavors. Taste and adjust seasoning with more Fine Salt and Black Pepper as needed, and remove the bay leaf, cinnamon stick and whole cloves or peppercorns before serving.
Serve the stifado hot with mashed potatoes, rice, or crusty bread to soak up the rich, spiced tomato-wine sauce.
