Preheat your oven to 325°F (163°C). Gather your ingredients and equipment, including a large Dutch oven.

Season your beef chuck with kosher salt and black pepper. In the Dutch oven, heat olive oil over medium-high heat, add beef in batches, and brown on all sides for 3-4 minutes.

Remove beef and add chopped onions, minced garlic, diced carrots, and celery to the pot. Sauté for 5-7 minutes until vegetables soften.

Stir in tomato paste and cook for an additional 2-3 minutes to deepen the flavor.

Add red wine, scraping up brown bits from the pot. Allow it to simmer for 3-5 minutes.

Return the beef to the pot along with beef broth, diced tomatoes, thyme, bay leaves, and Worcestershire sauce. Stir to combine.

Bring to a simmer, cover with a lid, and transfer to the oven. Cook for 2.5 to 3 hours, until beef is fork-tender.

If desired, create a roux by melting butter in a small pan and whisking in flour. Stir this mixture into the stew 15 minutes before serving.

Remove from oven, discard bay leaves, stir well, and taste for seasoning. Serve hot with crusty bread or a salad.