I bought some "cross rib roast" steak, which ends up being one of the toughest, chewiest cuts you can get off a cow. Damnitall. Here's a marinade that fixes tough steak. It takes some time to work, though.
Recipe makes enough marinade for 2 lbs steak, or roughly two large steaks.
Recipe
3 cloves minced or shredded garlic
1/4 cup soy sauce
1/4 cup pineapple juice (fresh is better than canned, but either will work)
2 tablespoons of olive oil
2 tablespoons of ketchup
1 teaspoon of dried oregano
1 teaspoon of ground black pepper
If steaks are frozen, thaw completely before using marinade. Mix all ingredients together into a sauce. Pierce through steaks or cross-cut deeply, both sides. Place steaks into a pan or tupperware container and cover with marinade, being sure that marinade covers all sides of each steak. Cover and refrigerate for a minimum of 24 hours, maximum of 48, turning steaks once and stirring up the marinade halfway through marinating time.
Broil steaks on broiling pan, roughly 3 to 5 minutes per side for inch-thick steaks. Thinner or smaller cuts will need less time.
Other solutions for tough steak include using more bromelain (protease enzyme from pineapple and other plants that breaks down protein), aging the meat as long as you dare in the fridge (defrost, then let sit for another 3 to 5 days), or grilling for a hell of a long time at low temperatures.
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