Preheat oven to 400°F with a rack in the center.
Cut the squash into ¼-inch thick rings (remove seedy centers with a biscuit cutter) or half-rings (halve squash first from stem to bottom and scoop out seeds with a spoon).
Line a baking sheet with parchment paper. Place squash slices on pan and toss with 1 tablespoon of the olive oil, ½ teaspoon of the salt, and ¼ teaspoon of the pepper, until evenly coated. Arrange squash in a single layer.
Roast until lightly browned and tender, about 30 minutes. You can flip the slices with a spatula halfway through if you like. Truth be told, I don't usually bother.
Strip the kale leaves from their stems and discard stems. Tear leaves into bite-sized pieces. Wash and dry thoroughly and place in a large salad bowl. Add the remaining two tablespoons olive oil, the vinegar, and the remaining ½ teaspoon salt and ¼ teaspoon pepper. Use your hands to massage the dressing into the kale.
Add the cabbage and onion to the bowl and toss well. Let it sit while you prepare the rest of the salad.
Set a small pan over medium heat and add walnuts and sugar. Keep a close eye on the pan as you cook, stirring occasionally at first and more frequently as you go along, to melt the sugar onto the nuts and lightly toast the nuts. Depending on your stove, this can take anywhere from about 90 seconds to 5 minutes.
To serve the salad, gently toss in most of the walnuts and pomegranate arils. Transfer to a wide, flat bowl or rimmed serving plate. Arrange the squash slices overtop and sprinkle with remaining nuts and arils. Drizzle with balsamic glaze.