Heat olive oil in a large 6qt heavy bottomed sauté pan (make sure you have a tight fitting lid for later or worst case scenario, be prepared to later cover your pan tightly with foil) over medium-high heat.
Pat the meat dry with paper towels to remove any moisture. Season the meat with salt and ground pepper and brown both sides in your heated pan. When the meat hits the pan it should sizzle. If it does not sizzle, it means your pan is not hot enough. Alternatively, if your pan is too hot, the olive oil will start smoking and, then well, you can start a nice little kitchen fire. Just keep the pan on medium/high heat, throw in one cube of beef as a test and if it makes a friendly but not aggressive sizzle, add the rest of your beef. The beef should fit in one layer with plenty of space in your pan. Based on the size of your pan, you may need to brown the meat in two sets. If your meat is over crowded it will steam and not brown which is no good for this sauce. (If you want to know why from a more authoritative scientific source than me, go look up Harold McGee + Maillard Reaction.).
Once you have browned all of your beef, remove and place in shallow bowl so as to collect accumulated juices. Turn the heat slightly down to medium and add diced pork to the pan, allowing it to render fat but not brown (about three minutes).
Add diced onion to pork, coat in fat and cook until translucent, but not brown, (about three to five minutes depending on how finely you have diced your onion). Stir occasionally with a wooden spoon to prevent browning.
Once the onion is translucent and NOT one moment before, add the garlic. If you add the garlic too soon it will quickly burn and ruin your entire sauce. If there is one way to ruin a meal and simultaneously piss off the entire country of Italy, it is too serve sauce with burnt garlic. Stir the garlic in the pork/onion mixture for about 60 seconds. If the garlic is starting to turn golden, add the wine, like, NOW!
Now that you have a mixture of fat, onion and garlic in your skillet, you have what is called a soffritto in Italian. Slowly add the wine to your soffritto. Deglaze the pan by stirring with a wooden spoon to release all the brown bits that are probably sticking to it by now. The wine should reduce by one half.
When your wine is finished reducing, return the beef and its accumulated juices to the pan and add the whole tomatoes and their juices.
Add the oregano, bay leaf (and if you have it, the outer rind of parmesan cheese), stir the beef to coat with sauce mixture and bring to a boil.
Once you have brought your ragù to a boil, lower the heat to a faint simmer, cover and cook for three hours. Ever so occasionally stir the sauce with a wooden spoon and break down the whole tomatoes as you stir. If you find that your ragù is drying out a bit you can add ½ cup of cold water and stir to incorporate. (NOTE: if you want to make this sauce in a slow cooker you can prepare through this step and then put in the slow cooker according to manufacturer instructions: generally on low setting for six hours and high setting for three hours. Don’t worry about stirring throughout braising process with this method but make sure to break up the tomatoes when the sauce is done slow cooking).
When your ragù has simmered for about three hours, it’s time to bring your pasta water to a rolling boil. Add salt to the boiling pasta water. For most Italians, the rule of thumb is 1 liter of water for every 100 grams of pasta, and add to that 10 grams of salt (known as the 1000/ 100/ 10 ratio of water/pasta/salt). If you want to actually measure out your water, salt and pasta go for it. I just bring a lot of water to boil, add a generous amount of salt and test to see if the water tastes brackish.
Once the salted pasta water is boiling viciously, add the penne, stir with fork so they don’t stick together and cook to al dente (usually about ten minutes for penne, and you can always taste the pasta if you are unsure). Do not be tempted to add olive oil to your boiling water. It will create an oil slick that will prevent the ragù from adhering to the pasta. You only add olive oil to fresh pasta, which is more delicate and has a tendency to clump together without the aid of olive oil.
When penne is cooked to al dente, drain it immediately and reserve about five tablespoons of pasta water.
Uncover your ragù, remove the bay leaf/ parmesan rind. Now add the drained penne and the reserved pasta water immediately (do not allow the pasta to rest and thusly become flaccid in a colander).
Raise the heat to medium high and stir with a wooden spoon to coat penne with sauce. If you are dexterous in the wrist, instead of stirring the pasta to coat you can flip it in the pan (this is the preferred Neapolitan method). Stir and cook for about one minute. This step of mixing the pasta and ragù is critical as it coats the pasta with the sauce and creates a unified dish.
Plate your penne ragù (I prefer using a shallow bowl), add a few gratings of Parmesan to taste, basil garnish and serve warm with bread.