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Heat half of the 4 tablespoons olive oil, in a large Dutch oven over medium-high heat. Season the 3 pounds chuck roast all over with salt and pepper.
Cook the roast for 3 minutes on each side to develop a browned crust. Remove the roast and set it aside on a plate.
Reduce the heat to medium and add the remaining olive oil along with the 3 large halved and sliced onions to the Dutch oven, cover and cook the onions, removing the lid to stir occasionally until tender and cooked down, about 10-15 minutes.
Remove the lid and cook for 10-15 more minutes, stirring occasionally until the onions are browned. While the onions cook, preheat the oven to 325 degrees Fahrenheit.
Once the onions are well browned (caramelized), add in 1 tablespoon minced garlic,1 teaspoon dried oregano, 1 teaspoon dried thyme, ½ teaspoon salt, and ½ teaspoon pepper, and cook for a couple of minutes.
Whisk the 2 tablespoons all-purpose flour into the onions, then slowly whisk in the 3 cups beef broth, 1 cup red wine, and 3 tablespoons Worcestershire sauce.
Add the roast back to the Dutch oven and spoon the gravy mixture over it. Place the lid on the Dutch oven and put it into the preheated oven.
Bake the roast for 4 hours or until the meat falls apart easily. Shred the roast and serve fresh!