Preheat your oven to 325°F (160°C). Pat the 4 pound chuck roast dry and season all over with the 2 teaspoons salt and 1 teaspoon black pepper.
Heat the 3 tablespoons olive oil in a large Dutch oven over medium high heat. Sear the roast for 4 to 5 minutes per side, until deeply browned all over. This crust is where a huge amount of the flavor comes from, so do not rush it. Transfer the roast to a plate.
Add the onion wedges to the pot and cook for 3 to 4 minutes, until they start to brown. Stir in the 4 cloves minced garlic and 2 tablespoons tomato paste and cook for 1 minute.
Pour in the 1 cup red wine, scraping up all the browned bits from the bottom, and let it reduce for 2 to 3 minutes. Add the 4 cups beef broth, 2 tablespoons Worcestershire sauce, the thyme, rosemary, and 2 bay leaves.
Return the roast to the pot along with any juices. Cover and transfer to the oven. Braise for 2½ hours.
Add the baby potatoes, carrots, and celery, nestling them around the roast. Cover and braise for another 1 to 1½ hours, until the beef is fork tender and the vegetables are cooked through.
Transfer the roast and vegetables to a platter and tent with foil. Fish out the herb stems and bay leaves.
To make the gravy, whisk the 2 tablespoons flour with a little water until smooth, then whisk it into the pot juices. Simmer on the stovetop for 3 to 4 minutes, until thickened.
Slice or pull the roast, spoon the gravy over everything, and sprinkle with the 2 tablespoons parsley.