Heat 1 tablespoon olive oil in a large dutch oven or oven-safe pot over medium high heat.
Add 3 pounds chuck roast to the pot and season it with 2 teaspoons salt and 1 teaspoon pepper. Sear the roast on all sides until browned.
Remove the roast from the pan. Add the garlic to the pan and cook for approximately 1 minute. Then deglaze the bottom of the pan with red wine.
Add 1 tablespoon minced garlic to the pot and cook for about 30 seconds until fragrant.
Pour in 1 cup red wine and scrape the bottom of the pot to release any browned bits.
Add ½ onion cut into large pieces, 4 carrots peeled and cut into large pieces, and 1 pound baby potatoes around the roast.
Pour in 2 cups beef broth and ¼ cup Worcestershire sauce. Sprinkle 1 teaspoon Italian seasoning over the top.
Cover the pot with a lid and transfer it to the oven. Bake for approximately 3 to 4 hours until the roast is tender and easily pulls apart with a fork.
Remove from the oven, let the roast rest for a few minutes, then serve warm with the vegetables and juices.
Notes
Refrigerate the leftovers in an airtight container for up to 5-7 days.