What version are you making, and what meat?
If starting with raw meat (as opposed to leftovers) then you need to follow the usual guidelines for the cut you use, whether it be chuck, round or tenderloin. Last time I made it (roughly following a Spanish recipe) I used ground beef, browned so it remained in chunks.
From the Wiki article:
"The original version of Ropa Vieja contained leftovers, but later became a shredded meat dish with garbanzo beans and potatoes in the Canary Islands.... The dish is a national feature of Cuba, and does not have garbanzo beans or potatoes in Cuba; it is just the shredded meat in sauce. "
First you have to use a fatty cut of beef. Sear that baby on both sides, add some onion, green pepper, lots of garlic, thyme, oregano, a can of diced tomatoes, & some chicken stock. Bring to a boil, cover & put in a hot oven (around 350) for 3-5 hours. When the meat is falling apart tender (could take longer depending on the the cut of beef) remove the meat from the pan, shred it & add back to the pan. Cool & refrigerate overnight. The next day, bring the pot to room temp & put the entire pot back in the oven w/o the lid at 350 until the liquid has evaporated by about half (you want some liquid, not completely dry). Serve with black beans & rice. You don't have to do this in 2 days, you could reduce the liquid & seve it the same day, it justs tastes better the next day. You could also saute the onion green pepper & garlic before adding it to the pot. It's not necessary to sear the meat, but it does help the flavor if you do. Totally up to you.
The cut of meat is a big factor. I often see recipes that use flank steak but I find that is too lean for my taste. The meat can get a bit dry and stringy. Other cuts that would work well is chuck and if you are looking for longer fibers a flap steak will sometimes be more marbled than a flank steak.
I only use skirt steak and I boil it before simmering in sauce. I've never had a problem with lack of tenderness. Stringy? Well, yes. It's the nature of skirt steak and ropa vieja does mean "old clothes," after all.
I'll try to dig up my recipe and post it when I get home.
I have no idea anymore where this recipe came from but it's reliably good.
2 lb. skirt steak or flank steak
1 tsp. salt
2 cloves garlic, crushed
1 bay leaf
3 Tbs. olive oil
1 small onion, finely chopped
3 cloves garlic, finely minced
1/2 c. tomato paste
1 1/4 c.reserved beef stock
2 Tbs. chopped pimentos
RInse steak, sprinkle with salt, and place in a stock pot. Ad garlic, bay leat, and water to cover. Cover and cook over medium-low heat 2 hours. Remove steak to cutting board and reserve 1 1/4 c. stock. Shred meat into very thin strips.
In a large skillet, heat oil and saute onion and garlic 1 minute. Stir in tomato paste, salt, and reserved stock Add steak and simmer over low heat 5 minutes, stirring occasionally. Add pimento, cover, and simmer 5 minutes more.
Serve over rice.
That sounds good and I want to try it when it's a little cooler. For that amount of cooking time and the OP's desire for tender, I would go with skirt steak. They are certainly not interchangeable. My most recent flanks steaks have been disappointing, and skirts are no brainers.
I made the Food & Wine Ropa Vieja with the boneless beef shoulder roast from Food & Wine and as far as the roast vs. flank steak went, that part was terrific. Very tender and lovely beef. I liked the flavors in the recipe, but *something* was missing, like mi_hiker said of the recipe below (very similar to Food & Wine's). I think if the beef had been cooked with wine or had either some more of a vinegar kick or some spicy heat in the background it would have been much better. As presently made, I'd give it a 3 or 3.5 out of 5.
Ropa Vieja (adapted from "A Taste of Old Cuba" by Maria Josefa O'Higgins)
(This serves 6 for a big dinner. It doubles or triples easily for a great buffet item.)
3 lbs beef brisket
1 sprig parsley
1 bay leaf
3 large onions, peeled and quartered
1 garlic glove, peeled
1 carrot, peeled and cut into chunks
1 tsp peppercorns
1 tsp salt
water to cover
2 large green bell peppers
5 garlic gloves, peeled and minced
1 tsp salt
½ tsp freshly ground pepper
¼ tsp dried oregano, or 1 tbsp fresh oregano
¼ cup bland vegetable oil, like canola
2 large onions, peeled and chopped
1 bay leaf
1 cup tomato sauce (not spaghetti sauce)
½ cup beef broth reserved from above
½ cup dry white wine
1 tbsp white wine vinegar
6-ounce jar of pimientos, drained, rinsed and sliced
To make the broth:
1) Put the brisket in a big pot and cover with water. Add the other ingredients and cover the pot.
2) Bring it to a boil over high heat, then turn down the heat and simmer, covered, for about two hours.
3) Remove the meat and let it cool. When it it cool, shred it with your fingers.
4) Reserve about ½ cup of broth for the sauce. Keep the rest for soup or something else.
1) Halve, stem and seed the green peppers. You need to fire-grill them, either on a grill or by placing them directly on a gas burner and turning the flame on until the skin is bubbled and a little black all around. (You also could do this in a pan on the stove, I suppose.) Let the peppers cool, then cut them into strips.
2) Mash the garlic, salt, pepper and oregano in a mortar and pestle, or you can run the garlic through a garlic press, then mash the rest of the ingredients into it with a fork.
3) Saute the onions in the oil until translucent in a big frying pan that has a cover. Reduce the heat, then stir in the garlic mixture and bay leaf. Cook for about 2 minutes.
4) Add the tomato sauce, broth, wine and vinegar. Simmer for about 5 minutes.
5) Add the pepper strips and the shredded meat, cover and let simmer for about ½ an hour. (Taste it after about 15 minutes to see if the flavors have blended and if the meat has heated through. You may need more salt and pepper.)
6) Fish out the bay leaf (if you can find it). Garnish with the pimientos.
This is great with some rice and black beans ("moros y cristianos") and an avocado salad.