Sear the beef: In a large Dutch oven or pot, heat the olive oil over medium-high heat. Season the beef with salt and pepper. Dredge the beef in flour, shaking off any excess.
Brown the beef: Cook the beef in batches, turning to brown on all sides. Remove the beef from the pot and set aside.
Sauté vegetables: Add the onion, carrots, and celery to the pot and cook until softened, about 5 minutes. Add garlic and cook for 1 minute more.
Combine ingredients: Return the beef to the pot. Add the diced tomatoes, beef broth, red wine (if using), bay leaf, thyme, rosemary, and oregano. Bring to a simmer.
Simmer: Reduce heat to low, cover, and simmer for 1.5-2 hours, or until the beef is very tender.
Serve: Remove the bay leaf. Serve hot with mashed potatoes, rice, or crusty bread.
Tips & Variations:
Slow Cooker: This stew can also be made in a slow cooker. Combine all ingredients in the slow cooker and cook on low for 6-8 hours, or on high for 4-5 hours.
Add-ins: Add other root vegetables like parsnips or turnips. You can also add mushrooms, peas, or pearl onions.
Spice it Up: Add a pinch of red pepper flakes or a dash of Worcestershire sauce for extra flavor.
Thickener: If the stew is too thin, stir in a slurry of cornstarch and water to thicken.
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