1/2 small kabocha squash, peeled, seeded, and cut into 1/2 inch cubes
5 TBS olive oil, divided
sea salt and black pepper to taste
4 shallots, peeled and thinly sliced
4 cloves garlic, peeled and thinly sliced
1 sprig fresh rosemary, needles finely chopped
1 chile de arbol, broken in half (or 1/4 tsp red pepper flakes)
1 bunch Tuscan kale, center ribs removed, torn into bite-sized pieces
1/2 cup white wine
1/4 cup golden raisins
1/2 lb. orechiette pasta (or other similar shape)
1/2 cup freshly grated parmesan cheese
Preheat the oven to 400F. Toss the cubed squash with 2 TBS of olive oil and spread out on a rimmed baking sheet. Season with sea salt and black pepper. Roast in the preheated oven until tender, about 25-30 minutes. Flip the squash cubes over halfway through cooking.
Bring a large pot of salted water to boil.
Heat 1 of the remaining tablespoons of olive oil in a large saute pan over medium-low heat. Add the sliced shallots, sliced garlic, chopped rosemary, and the chile de arbol to the pan. Saute until the shallots are soft and golden brown, about 5 minutes. Add the kale along with the remaining 2 tablespoons of olive oil. Season with sea salt. Cook the kale in the olive oil for 3-4 minutes, stirring frequently, then add the wine and the raisins to the pan. As soon as you add the wine, stir to scrape any burnt bits off the bottom of the pan.
Cook the kale over low heat for about 10 minutes. After 10 minutes, add the pasta to the boiling water. Continue cooking the kale while the pasta cooks. When the pasta is just barely al dente, use a skimmer to add the pasta to the pan with the kale. Add a few splashes of the pasta cooking water to the pan as well, along with the grated parmesan cheese. Add the roasted squash to the pan. Cook everything together for 2-3 minutes, stirring to fully coat the pasta in the sauce and to evenly distribute the vegetables. Serve immediately.