Place bacon in a cold skillet over medium heat. Cook until the fat has rendered and the bits are a deep, dark brown and audibly crispy. Drain on paper towels.

Wash and dry broccoli thoroughly. Cut into small, uniform florets. Slice the red onion into paper-thin purple slivers and cube the cheddar into small pieces matching the bacon bits.

In a separate bowl, whisk together the mayonnaise, sugar, apple cider vinegar, salt, and pepper until the mixture is thick, glossy, and opaque white.

Add the broccoli, bacon, cheese, and onion to a large bowl. Pour the dressing over and fold gently until every piece is saturated. Let sit in the fridge for 30-60 minutes to allow the dressing to pool slightly at the bottom.