Preheat the oven to 425 degrees F (220 degrees C). Line a sheet pan with parchment paper.
Split delicata squash lengthwise and scoop out seeds and strands. Cut each squash half crosswise into 1/2-inch-thick slices. Place squash pieces in a bowl and toss with olive oil, salt, black pepper, and ginger. Arrange on the prepared pan in a single layer.
Roast squash in the preheated oven for 8 to 10 minutes. Using tongs, turn each piece and continue to roast until squash is tender and lightly browned, 8 to 10 minutes more. Set aside to cool.
For the vinaigrette: Add pomegranate juice, olive oil, balsamic vinegar, Dijon mustard, honey, salt, white pepper, and cayenne to a jar with a tight-fitting lid. Cover and shake until well blended, about 30 seconds.
For the salad: Place kale, pear slices, pomegranate arils, and red onion in a large salad bowl. Cut squash into bite-sized pieces; add to the bowl. Shake vinaigrette again, then toss with salad.
Arrange salad on 4 plates and top with sliced almonds and crumbled bacon; garnish with cheese.
