Toss the eggplant in a tablespoon of olive oil and season with salt & pepper. Spread the eggplant on a baking sheet and roast 425°, stirring once about half to two-thirds of the way through the cooking time. The eggplant is done when it is golden and tender—about 20 to 25 minutes total. Set aside.
While the eggplant roasts, heat 2 T. olive oil over medium-high heat. Add the peppers and celery along with a generous pinch of salt. Sauté until they are just tender—about 10 to 15 minutes. The peppers will begin to caramelize a bit, but if the vegetables begin to color too quickly, reduce the heat. Add the garlic and cook until fragrant.
Add the Marsala sauce to the pan with the peppers and celery and bring to a simmer. Add the eggplant, capers, olives and oregano.
Season with salt & pepper and gently simmer uncovered for about a half hour, stirring occasionally, to allow the flavors to blend.
Bring 6 quarts of water to the boil in a large pot. Add 2 tablespoons of salt. Add the pasta and cook until al dente. When the pasta is ready, drain in a colander, being sure to reserve some of the pasta cooking water. Add the pasta to the sauce and toss well, adding some of the pasta water if the sauce seems dry.
Drizzle with a little olive oil and toss again. Serve with a generous shower of Pecorino. Serves 2 to 3, but this recipe easily doubles to serve 5 or 6.