Whisk the vinegar, honey and a pinch of salt and pepper in a large bowl. Add the kale, red onion and squash and toss. Massage with your fingers until everything is evenly coated and the kale softens slightly.
Heat the olive oil in a small saucepan over medium-high heat. Add the bacon and cook, stirring occasionally, until crisp, 10 to 12 minutes. Remove from the heat and stir in the rosemary. Let sit until it stops sizzling, about 1 minute.
Using a slotted spoon, transfer the bacon pieces to the salad. Pour the bacon drippings into a small bowl; you should have about 5 tablespoons (if you don't, add more olive oil to make up the difference). Add the warm bacon drippings to the salad and toss well; season with salt and pepper. Top with the pomegranate seeds.