Actually, it might not be a holly. This is in Rochester NY (zone 5-6-ish), eastern exposure, roots about 2 feet from blacktop driveway. A friend just moved into the house two days ago. We have no idea how the shrub was treated/managed in the past. Previous owner is very secretive about it, since she's deceased. Wind/frost could be the issue, but I'm wondering if soil could somehow be SO screwed up that it would cause what you see in the pictures.
Two pictures: