Place the sliced chiles in a mason jar or small bowl. In a small saucepan, add the water, red wine vinegar, sugar and garlic clove. Heat over medium heat until the sugar dissolves and the liquid reaches a light boil. Pour the hot vinegar mixture over the sliced chile, allow them to cool to room temperature. So here's the deal: if you have time, allow the chiles to pickle overnight. This is ideal. But if you don't, start this step first so the chiles have the longest time possible to pickle before you serve the dish.
Preheat the oven to 400 degrees F. Rub the butternut squash with a teaspoon or two of olive oil and place the squash halves flesh-side down on a parchment-lined baking sheet. Transfer to the oven to roast for 20-30 minutes, until the squash is tender when poked with the tines of a fork.
Scoop out the butternut squash flesh and transfer to a blender or food processor. Add the minced garlic, pour in the heavy cream and melted butter. Blend until very smooth, about a minute. Add a few pinches of salt to taste and then set aside.
To a large pan, add two tablespoons of butter. Cook until the foam and bubbles subside and the butter turns brown in color and smells wonderful and nutty, about 2-3 minutes. Add the kale leaves and cook for 1 to 2 minutes. Pour in the butternut squash puree and heat until very warm.
Meanwhile, bring a liberally-salted pot of water to a boil. Cook the pasta for about 30 seconds to a minute, until al dente. Transfer the pasta to the skillet with the butternut squash sauce, along with a few chiles; toss the pasta until completely coated. Divide between plates. Top with a dollop of ricotta, a sprinkling of black pepper and a drizzle of pumpkin oil. Serve immediately.