Preheat oven to 400°F
Place the cubed butternut squash on a baking sheet and coat in the light olive oil and season with the salt and pepper.
Place the thick cut bacon on a rack with a drip tray below it.
Bake both the butternut squash and the bacon for 15-20 minutes until the squash is fork tender and the bacon has crisped up and rendered. Be sure to flip the bacon over 10 minutes through. Once cooked, remove and set aside both the squash and bacon to cool. Roughly chop the cooled bacon crosswise into strips. While the butternut squash and bacon are baking, blanch the broccoli by bringing 6-8 cups of water to a rolling boil and dropping the broccoli in. Let the broccoli cook for 1-2 minutes before removing and immediately placing the florets into an ice bath. Once cooled, drain and pat the florets dry with paper towels or a clean kitchen towel to remove any excess moisture.
Assembly: In a large bowl, combine the red cabbage, red onion, and chopped pecans in a bowl.
Add the cooled and thoroughly drained broccoli florets, cheese, the cooked and cooled squash, cranberries, and dressing. Toss lightly to distribute the dressing.
Finally, top with the chopped bacon and lightly toss once again to distribute the bacon. Do not over mix..
Serve immediately or place into the refrigerator for up to five days and enjoy chilled.