Preheat oven to 400 degrees F.
Peel butternut squash, seed, and slice into ¼ inch thick slices. Toss with 2 tablespoon olive oil, salt, and pepper. Roast in the oven for 20-25 minutes or until tender and lightly browned. Remove from heat and set aside.
Toss 2 cups brussels sprouts with 2 tablespoon olive oil, salt, and pepper. Roast for 15 minutes. Combine the juice of 1 orange with 2 tablespoon honey and toss the brussels sprouts in the juice. Roast for another 3-4 minutes or until lightly charred. Remove from heat and set aside.
Toss 2 cups day-old cubed bread with ½ teaspoon garlic powder, sprinkle of sea salt, and 2 tablespoon olive oil. Bake until golden brown, about 7-8 minutes. Remove from heat and set aside.
Spread the prosciutto on a baking sheet and bake for 10 minutes or until crispy. Remove from heat and let cool.
Make the lemon herb vinaigrette. Blend together 3 tablespoon lemon juice with 2 teaspoon dijon mustard, ½ cup parsley, 1 teaspoon garlic, 1 teaspoon salt, and ½ teaspoon black pepper. Slowly add ½ cup olive oil with the blender on until all of the oil is incorporated. Taste the salad dressing for seasoning, adjusting as needed.
Assemble the salads. Plate mesclun greens into a bowl topped with the roasted butternut squash, brussels sprouts, garlic croutons, crispy prosciutto, pomegranate, and sliced manchego. Serve with lemon herb vinaigrette.