Pat the chuck roast dry with paper towels. Season all sides with the salt and pepper.
Heat the olive oil in a large Dutch oven over medium-high heat. Sear the roast for 3-4 minutes per side until well browned. Transfer the roast to a plate.
Reduce the heat to medium. Add the minced garlic and cook for about 30 seconds, stirring constantly until fragrant.
Pour in the red wine and scrape the bottom of the pot with a wooden spoon to loosen all the browned bits. Simmer for 2-3 minutes.
Return the roast to the Dutch oven. Arrange the onion, carrots, and potatoes around the roast.
Pour in the beef broth and Worcestershire sauce. Sprinkle the Italian seasoning over the liquid and vegetables.
Cover tightly with the lid and bake for 3½-4 hours, or until the roast is fork tender and easily shreds.
Remove the roast from the oven and let it rest for 10-15 minutes before slicing or shredding. Serve with the vegetables and spoon the cooking juices over the top.
Notes
Chuck roast is the best cut because its marbling becomes incredibly tender during the long cooking time.
Use a dry red wine such as Cabernet Sauvignon, Merlot, or Pinot Noir. If you prefer not to cook with wine, substitute an additional cup of beef broth.
If the vegetables become softer than you prefer, remove them during the last 30 minutes of cooking and keep them warm while the roast finishes.
For extra-rich gravy, strain the cooking liquid into a saucepan and simmer until slightly reduced, or thicken it with a cornstarch slurry.