Preparing and Searing the Beef
Pat 3 pounds beef chuck roast dry and season all sides with 1 tablespoon coarse kosher salt and 1 teaspoon black pepper. Heat 2 tablespoons olive oil in a large Dutch oven or heavy pot over medium-high heat. Sear the roast for about 3–4 minutes per side until a deep brown crust forms, then remove and set aside.
Building the Vegetable Base
In the same pot, add 1 sliced yellow onion, 4 peeled and chopped carrots, and 4 chopped celery stalks, cooking for about 5 minutes until they begin to soften. Stir in 4 chopped garlic cloves and cook for about 30 seconds until fragrant.
Deglazing and Adding Liquids
Pour in ½ cup red cooking wine, scraping up any browned bits from the bottom of the pot. Let it simmer for 2–3 minutes to reduce slightly. Add 6 cups beef broth (or water with Better Than Bouillon) and (2) 15-ounce cans diced tomatoes (with juices), stirring to combine.
Adding Barley and Seasoning
Stir in 1 cup dry pearled barley, 1 teaspoon dried oregano, and 1 tablespoon dried Italian seasoning blend, mixing well.
Braising the Roast
Return the seared roast to the pot, nestling it into the liquid. Bring to a gentle simmer, then cover and cook on low heat (or in a 325°F oven) for about 2½–3 hours until the beef is tender.
Adding the Potatoes
About 45 minutes before the end of cooking, add 4 diced Yukon gold potatoes (skin on) to the pot. Continue cooking until the potatoes and barley are tender and the stew has thickened.
Finishing and Serving
Remove the roast and either slice or shred it, then return it to the pot. Stir everything together and taste, adjusting seasoning if needed. Serve hot, allowing the rich broth, tender beef, vegetables, and barley to come together into a hearty stew.
