Rub roast with 1 teaspoon fresh ground pepper. In a dutch oven (or large pot), heat olive oil on medium high. Sear roast, flipping on all sides until well browned (about 10 minutes).
Add wine, parsley, thyme, salt if using, remaining 1 teaspoon pepper, garlic cloves, onion, carrots, potatoes, and celery. Add tomatoes over top.
Cover and bake for 3 ½ hours. Check for doneness by using a fork to see if meat is tender. If meat is not tender, bake for 30 more minutes.
Remove from oven, remove thyme sprigs, and place meat on a cutting board. Put vegetables in a dish and cover (if thickening gravy).
Pull meat, or slice against the grain. Serve with vegetables and juices or gravy.
To thicken gravy, place dutch oven on medium high heat and bring liquid to a boil. Meanwhile, mix cornstarch and water slurry together and set aside. Once liquid has reached a boil, stir slurry and add about half to the liquid, stirring to thicken. Add more slurry until gravy reaches desired consistency.