Step 1

Set a large pot of water with some salt on the stove to bring to a boil for the pasta.

Step 2

Meanwhile, place a large skillet or other pan over medium heat with some oil; add the onion, black pepper, and some salt and cook until the onion starts to soften, about 3 minutes. Add the garlic, Italian seasoning, and red pepper flakes and cook until fragrant, 1 minute more.

Step 3

Add the eggplant and olives, season with salt, and cook, stirring regularly and adding more oil as needed, until the eggplant has softened, about 10 minutes. Add the tomato paste and cook for 2 minutes more. Deglaze with the red wine, scraping up any stuck on bits from the bottom of the pan and stirring it all together.

Step 4

Add the crushed tomatoes to the eggplant (swish about 1/2 cup water around the can and add that to the skillet to to make sure you get all of the tomatoes) and let simmer gently, stirring regularly, for 15 minutes. Add in the fresh oregano, if using, for the last minute or 2 of cooking.

Step 5

Meanwhile, cook the pasta in the salted boiling water until just shy of al dente. Reserve some of the pasta cooking water and then drain the pasta.

Step 6

Mix the pasta into the sauce along with some of the reserved pasta cooking water (about 1/4 cup) and let it all cook together until the pasta is al dente, 1 to 2 minutes. Taste and adjust for seasoning. Serve with some Parmesan cheese sprinkled on top.