Heat a large dutch oven or heavy-bottomed stock pot over medium-high heat, and add 2 tablespoons of olive oil. Pat the beef cubes dry with paper towels. Season them with salt and pepper.
3 tbsp Olive oil
Brown the beef on all sides. Do this in batches, don’t overcrowd the pan. Remove the meat to a plate, and set aside.
2 lbs Chuck roast
Add the remaining tablespoon of olive oil. Add the carrots, celery, and onions and saute for about 5 minutes, add the tomato paste and minced garlic. Saute for about 30 seconds until fragrant.
3 medium Carrots, 2 large Celery ribs, 1 medium Onion, 1 tbsp Tomato paste, 4 cloves Garlic
Add the red wine, and boil for about 2 minutes while scraping the brown bits up from the bottom of the pan.
1/2 cup Red wine
Add the browned beef back to the pan with the thyme, Worcestershire sauce, and beef broth. Bring to a boil, reduce the heat to a simmer, cover, and simmer for 45 minutes stirring occasionally. The beef cubes will not be fall apart tender at this point.
1 tbsp Worcestershire sauce, 4 sprigs Fresh thyme, 6 cups Low-sodium beef broth
Add the barley, cover, and simmer for 45-60 minutes until the barley is tender stirring occasionally. Barley is done when it is tender, yet slightly chewy. This is when the beef should be ultra tender!
3/4 cup Pearl barley
Season to taste with salt and pepper. Stir in the fresh parsley and remove the thyme stems.
1/2 tsp Kosher salt, 1/2 tsp Black pepper, 1/4 cup Fresh parsley