2 pounds butternut squash, peeled and cut into ? inch cubes
1 cup plus 2 tablespoons extra-virgin olive oil
2 tablespoons unsalted butter
4 ounces prosciutto, thinly sliced
2 cinnamon sticks
? pound sweet onion, preferably Spanish, cut into ? inch dice
? pound carrots, peeled and cut into ? inch dice
? pound celery, peeled and cut into ? inch dice
1 heaping tablespoon fresh chopped sage leaves
2 quarts chicken stock
18 amaretti cookies
? cup heavy whipping cream
Kosher or sea salt and freshly ground black pepper
1. Preheat oven to 400 degrees F. In a large bowl, toss the butternut squash with 2 tablespoons of the olive oil, butter, and salt to taste. Transfer to a large baking sheet in a single layer and roast until caramelized and tender, about 20 minutes, stirring occasionally.
2. Meanwhile, in a large stockpot over medium, heat the remaining � cup olive oil for 10 minutes. Add the prosciutto and cook, stirring often, until crispy and deep red. Transfer with a slotted spoon, being careful for splattering oil, to paper towels until ready to serve.
3. To the same pot, add cinnamon sticks, onion, carrot and celery and cook over medium for 10 minutes. Remove the pot from the heat and set aside until the squash is finished cooking.
4. When the squash is done, add it to the stockpot with the cooked vegetables. Add the sage and cook over medium-high, stirring, for 1 minute. Add the chicken stock, bring to a simmer, and cook for 10 minutes. Crumble in 15 of the amaretti cookies and cook for 5 minutes, until the soup begins to thicken.
5. Remove the cinnamon sticks and puree in a food processor or blender in batches. Return the soup to the pot, add the cream, bring back to a gentle simmer and taste for salt and pepper.
6. To serve, ladle into individual bowls and top with the crispy prosciutto and the remaining amaretti cookies, coarsley crumbled.
Adapted from The Chef of Cucina Amore: Celebrating the Very Best in Italian Cooking: Publishers' Group West; Copyright 1999 West 175th Enterprises, Inc.
Joe Simone says that the richness of this soup comes from slowly roasting the squash and then cooking it in a small amount of chicken stock. The amaretti cookies provide some thickening as well as a wonderful sweet complement to the soup. The amount of stock may need to be adjusted. You need only enough to barely cover the ingredients in the stockpot.