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Preheat the oven to 325 degrees F.
Season the chuck roast with salt and pepper.
Place a large Dutch oven over medium heat and add the canola oil, once hot, add the meat and brown it on all sides, 3-4 minutes on each side, then set it aside. It should be nicely browned!!
Add the diced onion, and minced garlic to the Dutch oven, stir, and cook for 1 minute, add chopped thyme, chopped rosemary, dried oregano, and dried Italian herbs, stirring frequently before adding in the tomato paste, and cook for about 1 minute.
Add in the beef broth, Worcestershire sauce, and red wine and scrape the bottom of the pan, then add the roast.
Add the quartered onion, whole garlic cloves, carrots, rosemary sprigs, and bay leaves.
Cover and cook in the oven for 3-4 hours or until fork-tender. Let the roast rest for 20 minutes before serving.