Start a large pot of salted water to boil for the pasta at the same time you start a medium sauce pan of salted water to boil for the kale.
While the water is heating, remove the kale leaves from the spiny ribs and rough chop into large chunks. Eyeball the amount till you have about 5-6 cups of loosely packed leaves.
Once the water for the kale starts to boil, add the kale and boil, stirring occasionally for a good minute. Scoop out about one cup of the water at the end of this step and pour kale into a collander.
The water for the linguine should be soon ready; boil according to package directions until al dente.
Take the kale and place in a couple layers of paper towels; wrap the kale and press well to remove almost all excess moisture. Place the kale into a food processor. Set aside while preparing other ingredients for the pesto.
In a small heavy bottom pan, toast the walnuts. This step helps reduce some of the bitter flavor in the walnuts and adds a nice toasty note. Put the walnuts into the food processor with the kale. (Save this pan because you'll use it to carmelize the shallot in a minute.)
Add the garlic and finely chop with the kale and walnuts and 1/2 teaspoon salt. With the motor running, slowly add the extra-virgin olive oil until the pesto is smooth. You might need to stir down the ingredients and pulse several times to get all the ingredients well mixed. The pesto will seem like a thick paste at this point. Set aside.
Place the shallot in the same pan you cooked the walnuts and let cook until soft and just starting to blacken.
Now you're ready to put all the ingredients together and this is where exact amounts don't matter:
In a large bowl, combine the linguine and pesto. Add some of the reserved kale water to help the pesto thin and spread throughout the linguine (If needed, heat the water first to help re-heat the dish to serve hot).
Add the shallot, capers, halved black olives and toss.
If adding the Romano cheese, grate about 1/2 to 1 cup cheese into the linguine and toss. Taste and add more cheese, olives and capers as desired (I like to add enough olives and capers so to get some in every bite).
Dish into individual bowls and grate more cheese on top. With a sharp knife, cut shavings into the chocolate (or use a microplane or fine grater) and top each serving with the chocolate.
Refrigerate any leftovers up to 4 days in the refrigerator.