Heat a large Dutch oven over medium-high heat. Coat pan with cooking spray. Add 1 steak to pan; cook 2 1/2 minutes on each side or until browned. Remove steak from pan. Repeat procedure with cooking spray and remaining steak.
Reduce heat to medium. Add onion, bell peppers, and garlic to pan; cook 7 minutes or until tender, stirring frequently. Stir in olives and next 5 ingredients (through black pepper); cook 30 seconds or until fragrant. Stir in vinegar, scraping pan to loosen browned bits; cook for 2 minutes or until liquid almost evaporates. Stir in broth, tomato paste, and bay leaves. Add steaks; bring to a simmer. Cover, reduce heat, and cook 1 1/2 hours or until steaks are very tender. Discard bay leaves.
Remove steaks from pan; shred with two forks. Stir shredded beef and cilantro into pan.
Wine note: A savory beef dish such as this needs a rich red wine, but preferably one that won't break the bank since this is a humble meal. One of my favorites is Reds, a delicious blend of several varietals, with zinfandel predominating. And the 2005 is $9. —Karen MacNeil