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First, look at the cut of the beef. Meat from the part of the animal that works the least, i.e. the tenderloin, short loin, top portions of the rump, is gonna be more tender than meat from the parts of the animal that work a lot, such as the chuck (front shoulder), brisket, bottom rump, etc. If you're planning on cooking the meat using a dry heat method (broiling or roasting), go for cuts from the tender section of the cow. For moist heat methods (braising and stewing), meat from the less tender sections is fine, and may be preferable because of the additional flavor found in these cuts.
Next look at color. The nice, red meat you associate with a good piece of cow is NOT gonna be particularly good eating. Ideally, the meat should be a darker, less appetizing color, which means that the enzymes in the meat have been working a bit, and some aging has taken place.
Now, look at the cut of meat itself. If it looks nice and lean, with no fat marbling in the meat itself, forget it. If you broil meat like that, it's gonna be tough as the proverbial boot. Instead, choose the piece that everyone else is rejecting 'cause it has some streaks of fat in the middle of the meat, maybe a little more outside fat coating than is politically correct.
Also look at the texture of the meat. All muscle contains two kinds of connective fibers, called collagen and elastin. These fibers bundle the individual strands of muscle together, and allow the muscle bundles to function. When exposed to heat, they contract, toughen, and make the end product tough. In dry heat cooking, look for a piece of meat with a velvety surface, indicating that these bundles are not overly developed.
In moist heat cooking, collagen softens and dissolves, and becomes gelatin. Elastin, unfortunately, doesn't do much of anything except transform itself into gristle.
Finally, if in any doubt whatsoever as to the overall tenderness of the meat, you can resort to treating meat to be broiled with a commercial meat tenderizer containing papin. If you follow the directions exactly (more/longer exposure to this enzyme is NOT better, and will result in a flabby, disgusting mouthfeel), you can get a pretty decent steak out of some fairly unpromising hunks of meat.
Another hint, which your nephew Wes learned the hard way the other night, is to avoid steaks with strange, butcher-generated names like the plague. He dragged home a couple of little beauties with the colorful name of "Ranch Steaks" the other night. (I tried to tell him not to buy 'em cause they were gonna be tough, but he didn't seem to hear me :-) He tossed his on the grill, chewed, cussed and chewed his way through as much of it as he could manage before consigning the remainder to the cat. I treated mine with papin, cooked it very rare, and got something that was marginally edible.
Moral to the story: If the butcher doesn't thing it will sell under its REAL name (in this case Sirloin Tip, which is a polite way of saying Heel of Round), he's gonna give it a fancy handle and mark the price up 50 cents a pound, just to see who's gullible enough to buy it.
Have to agree with Jeff, though. The quality of beef has gone WAY down recently. Guess its the move toward leaner, lighter beef that's the culprit. I've said it before, and I'll say it again -- there's NO WAY lean, unmarbled beef is going to even begin to approach the succulence and tenderness of the old-fashioned, un-heart healthy stuff we grew up on. Personally, I'd rather feast on the real thing a couple of times a year than gnaw my way through my regular portion of the tasteless, tough junk we're being subjected to these days.
I realize that in a changing world, the production of old-fashioned, grain fed beef is ecologically unsound. In a world with limited resources, we just can't devote that much time/grain to feeding a cow for my pleasure. But there must be some sort of compromise.
Personally, I'd rather have a little bit of something REALLY good occasionally, than a lot of something mediocre on a regular basis.
I yield the soapbox to the Gentleman from Maryland (or whoever else wants to climb on).
Kathy in Bryan, TX