Directions

1. 1

   Pat the beef chuck roast dry with paper towels. In a small bowl, combine the dried oregano, ground cumin, salt, and pepper to create a seasoning rub.

2. 2

   Rub the entire surface of the beef roast generously with the oregano-cumin mixture, ensuring even coverage on all sides.

3. 3

   Heat the vegetable oil in a large, heavy-bottomed pot or Dutch oven over medium-high heat until shimmering.

4. 4

   Carefully place the seasoned beef roast into the hot oil. Sear all sides until deeply browned, about 3–4 minutes per side. Transfer the roast to a plate.

5. 5

   In the same pot, add the sliced onion, diced green pepper, diced red pepper, and minced garlic. Sauté over medium heat for 3–4 minutes until the vegetables soften slightly, stirring occasionally.

6. 6

   Add the water to deglaze the pot, scraping up any browned bits from the bottom with a wooden spoon.

7. 7

   Stir in the can of crushed tomatoes and the pimiento-stuffed green olives (including their liquid for extra flavor).

8. 8

   Return the seared beef roast to the pot, nestling it among the vegetables and sauce. Bring the liquid to a gentle simmer.

9. 9

   Reduce the heat to low, cover the pot partially with a lid, and simmer slowly for 9–10 hours (or until the beef reaches an internal temperature of 145°F and is extremely tender when pierced with a fork). Stir and turn the roast every 2–3 hours.

10. 10

    Once the beef is fall-apart tender, remove it from the pot and transfer to a cutting board. Let it rest for 10 minutes, then shred or slice into bite-sized pieces.

11. 11

    Return the shredded beef to the pot, stir gently to combine with the sauce and vegetables, and adjust seasoning with additional salt and pepper as needed.

12. 12

    Serve hot, dividing the beef and vegetable mixture equally among 12 portions, spooning the rich olive-tomato sauce over each serving.