Any tough meat will be more tender when braised. Just cook them slowly covered in the oven or a crockpot with a little liquid. It can be water,broth or even apple or cranberry juice diluted with water.

can't go wrong if you follow this method by Marcella Hazan

Pork Loin Braised in Milk, Bolognese Style

- serves six -

"If among the tens of thousands of dishes that constitute the recorded repertory of Italian regional cooking, one were to choose just a handful that most clearly express the genius of the cuisine, this one would be among them," Hazan writes, going on to praise the utter simplicity of this braise; I had to try it. I think something went wrong with my sauce, which never turned nut-brown and clustery as described, but the pork was moist and tasted wonderfully of itself, as Greenmarket pork usually does.

Ingredients
1 tablespoon butter
2 tablespoons vegetable oil
2 1/2 pounds pork rib roast (meat detached from the ribs in one piece, ribs carved into 2 or 3 sections) or 2 pounds boneless Boston butt (will carve less neatly, but thats what I used); do not have any fat trimmed away from either cut of meat (youÂll be able to spoon it away at the end of cooking)
Salt
Freshly ground black pepper
2 1/2 cups (or more) whole milk

Procedure
1. Heat the butter and oil over a medium high flame in a heavy-bottomed pot that will accommodate the pork snugly. When the butter foam subsides, put the meat in, fat side facing down. As it browns, turn it every few moments for even coloring all around. If you should find the butter becoming very dark, lower the heat.

2. Add the salt, pepper, and 1 cup of milk. Add the milk slowly, or it will boil over. Allow the milk to come to a simmer for 20 or 30 seconds, turn the heat down to a minimum, and cover the pot, leaving the lid slightly ajar.

3. Cook at a very lazy simmer for about 1 hour, turning the meat from time to time, until the milk has thickened, through evaporation, into a nut-brown sauce. (The exact time it will take depends largely on the heat of your burner and the thickness of your pot. In my case, there was such a thick layer of fat on top of the milk that I couldnÂt really tell what was going on beneath it. It didnÂt seem to me it was ever going to turn nut-brown, and so eventually I forged ahead anyway, which may explain my sauceÂs less than successful final aspect.) When the milk reaches this stage and not before, add 1 more cup of milk, let it simmer for about 10 minutes, then cover the pot tightly. Check and turn the pork from time to time.

4. After 30 minutes, set the lid slightly ajar. Continue to cook over minimum heat, and when you see there is no more liquid milk in the pot, add the other 1/2 cup milk. Continue cooking until the meat feels tender when prodded with a fork and all the milk has coagulated into small nut-brown clusters. Altogether it will take between 2 1/2 and 3 hours. (If, before the meat is fully cooked, you find that the liquid in the pot has evaporated, add another 1/2 cup of milk, repeating the step if necessary.)

5. When the pork has become tender and all the milk in the pot has thickened into dark clusters (again, this didnÂt look as if it was ever going to happen for me), transfer the meat to a cutting board. Let it settle for a few minutes, then cut it into slices about 3/8 inch thick or slightly less, and arrange them on a warm serving platter.

6. Tip the pot and spoon off most of the fatÂthere may be as much as a cup of itÂbeing careful to leave behind all the coagulated milk clusters. Add 2 or 3 tablespoons of water, and boil away the water over high heat while using a wooden spoon to scrape loose cooking residues from the bottom and sides of the pot. Spoon all the pot juices over the pork and serve immediately.

Pork is lean now a days...even leaner when "home grown"...just don't over cook..I like my pork pink..especially home grown..

brining should help. I just use salt and water..but you can add flavors/seasonings..maple syrup, brown sugar...give it a google search, maybe you can come up with something that fits yours and his tastebuds...
Does he like crust on his food? Dipping them in buttermilk, yogurt, mayo, mustard and then pressing in crumbs...and baking.

Have you tried marinating them overnight in Coke (or a similar carbonated product)? That sometimes helps.

One of the problems with pork nowadays is that it is so lean. Many chefs recommend brining pork and chicken to make them more tender.

Just a word of caution. I'd be careful about undercooking.

In the 'old days' most hogs were grown in barnyards and hogs tend to root around in whatever they live in. Trichinosis was a real problem and the recommendation was to cook pork very well to kill any potential parasites. Now, that recommendation isn't made any more, because most hogs are raised in cement feedlogs which are kept a lot cleaner then any barnyard could be.

When you buy pork direct from a small farmer it could very well be barnyard raised. Don't eat this pork rare unless you know for sure that it was raised on cement.