In a large bowl, toss 3 cups of butternut squash, peeled and seeded, cut into large chunks. Add 1/2 cup orange juice, 1/3 cup dark brown sugar, and 1 cinnamon stick. Pour into roasting pan and cover with aluminum foil. Bake in a preheated 450 degree oven for 1 hour or until tender. Discard cinnamon stick, drain and set juice aside.
In a heavy bottom stock pot place 1/4 cup sweet butter, 1 cup leeks, white part only - rough chopped, 1/2 cup onion and 1 granny smith apple - peeled, cored and chopped. Cook slowly over a medium flame, stirring frequently until very tender. Do not allow to color. Add 4 C chicken stock or vegetable bouillon. Bring to a low boil. Add squash, but not the squash juice. Cook for five minutes and add the optional 1/3 cup heavy cream and simmer for about 5 minutes. Cool and puree with a hand blender till very smooth.
In a non-stick saute pan, over a high flame place 1/4 cup extra virgin olive oil. When it begins to smoke, add 1 cup of butternut squash, diced into small pieces. Stir until slightly colored. Add the reserved "juice" from the squash that was made earlier. Cook until all the liquid evaporates and the squash is lightly glazed. Reserve in a warm place.
Place 1/4 cup sage leaves, 1/8 cup Italian parsley and 1/2 cup Canola oil in a blender with a few ice cubes. Blend at high speed till very smooth. Pour into a cup and refrigerate.
In a small pan with a little peanut oil, fry 6 large sage leaves till crispy and drain on paper towels.
Ladle squash soup puree into six warm bowls. Sprinkle glazed, diced squash evenly over bowls, and drizzle about one teaspoon sage oil over each, and lay one sage leaf on each soup. Serve immediately.