Pat the chuck roast dry with paper towels and season generously with salt and black pepper.
3 pounds boneless chuck roast, Salt and black pepper
Heat the olive oil in a large Dutch oven over medium-high heat. Sear the roast for 5–7 minutes per side until deeply browned. Remove from the pot and set aside.
2 tablespoons extra virgin olive oil
Add a little more oil if needed, then add the sliced onions with a pinch of salt and pepper. Cook over medium-low heat for about 25 minutes, stirring occasionally, until the onions are soft and caramelized.
3 pounds yellow onions
Stir in the garlic and Worcestershire sauce and cook for 1–2 minutes until fragrant. Pour in the red wine, scraping up any browned bits from the bottom of the pot. Sprinkle in the flour and stir well.
4 garlic cloves, 1 tablespoon Worcestershire sauce, 1 tablespoon all-purpose flour
Add the beef broth, bay leaf, and thyme. Return the roast to the pot, making sure it is mostly covered by the liquid.
2½ cups beef broth, 1 cup red wine, 1 bay leaf, 1 sprig fresh thyme
Cover and transfer to a 300°F (150°C) oven. Cook for 3–4 hours, until the meat is tender and easily pulls apart with a fork.
Let the roast rest in the sauce for 10–15 minutes before slicing or shredding.
Serve warm with the rich onion gravy spooned over the top.