After about 5 minutes, add your oregano, cumin, and stir in.
If you're planning on eating right away, this'd be a great time to put a pot of water on the stove to boil for your pasta. If not, you can do it later (the sauce can go into a holding pattern down below).
After another 5ish minutes, add your anchovies and capers to the pan.
And again, after 5 minutes, turn the heat on the pan down to low, and add your red pepper flakes, salt, pepper, caper brine, and olives.
Another 5 minutes, and you'll want to add the red wine and pine nuts and allow it to simmer for another 5.
All total, just around 25 minutes.
And here's a good place to stop and wait for guests or any number of other things, without worrying that the meal will be ruined. Just kill the heat on the pan.
OK - your pasta is just about done. How do you know if it's done? When you throw it against your fridge it sticks. I don't care what people have told you, you should use a fridge, not a 9 foot ceiling, to test it.
Pasta done? Great. Again, you can pause dinner here if you need to.
Next, drain your pasta, put back in pot over low heat. Now, put colander over the pot that has your pasta in it, and loosely strain some of the liquid part your sauce through colander. Toss the pasta thoroughly with the sauce.
Now set up your plates. Put a little blanket of arugula on each plate, and twirl pasta into a nest with tongs, placing it on the arugula so it wilts. Spoon the chunky part of sauce over twirled nest of pasta. With a paring knife or vegetable peeler shred the parmesean cheese over the plates, and scatter some red pepper flakes and pine nuts around the plates for garnish.