In a large pot heat the olive oil over medium high heat. Add about half of the stew meat. Season with about half of the salt and some pepper. Allow it to sear undisturbed for about 5 minutes.
Flip and repeat on all sides until the meat is brown. Remove from the pan and set aside. Repeat with the remaining beef.
Reduce the heat to medium low. Do not drain any of the grease. Add the onion. Sauté for about 5 minutes.
Add garlic, brown sugar and Italian seasoning. Sauté for 2-3 minutes or until fragrant.
Pour in the beef broth, tomato paste, bay leaves. water, and Worcestershire. Add all of the beef and any juices back to the pot.
Bring to a boil, cover, and reduce the heat to medium low (or low depending on your stove). Cook covered for 1.5 hours.
Add the carrots and potatoes. Cover.
Cook covered for another hour or until the vegetables are cooked to your liking. Add chili and green pepper. Serve and enjoy.
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