Season the chuck roast generously with salt and pepper on all sides.

In a large oven-safe Dutch oven or skillet, heat the olive oil over medium-high heat. Once hot, add the chuck roast and sear it until it's well-browned on all sides. This step helps lock in the flavors and juices. Remove the roast from the pan and set it aside.

In the same pan, add the diced onion, celery, carrots, and minced garlic. Sauté them for about 5-7 minutes until they begin to soften and the onions turn translucent.

Stir in the diced tomatoes and red wine, scraping up any browned bits from the bottom of the pan. Let it simmer for a few minutes to allow the alcohol to cook off and the flavors to meld.

Place the seared chuck roast back into the pan on top of the vegetables.

Pour in the beef stock and sprinkle thyme and sage over the roast. These herbs will infuse the roast with aromatic flavors.

Cover the Dutch oven or skillet with a lid or foil and transfer it to the preheated oven. Roast for about 3-4 hours or until the roast is fork-tender and easily pulls apart. Baste the roast with the liquid occasionally during cooking.

Once done, remove the roast from the oven and let it rest for a few minutes. Slice or shred the meat as desired.

Serve the tender chuck roast slices with the flavorful vegetables and the rich pan juices as a gravy.