They haven't been there for 100+ years. I guarantee you that when they cut them down and age them, they'll be shown to have been there between 60-80 years, at best.
And, Quercus virginiae are not well suited for either that climate, that urban location, and both.
You can get those trees to grow there, but it has to be under pristine conditions and you have to use a lot of resources to make it happen. That means careful pruning, careful watering and careful fertilization. It also means nearly constant soil-testing and constant adjustments to soil chemistry to overcome the climatic limitations.
What you can't do is pave over the permeable surfaces above their roots, coat the damned things with toilet paper and then power wash them when they're trying to set acorns or drop their leaves. Those trees were doomed years ago, and by their actions, not Updyke's.
I still hate that this buffoon did what he did and gave them a reason to blame us for their demise. But it doesn't change the fact that those trees' demise is their own. damned. fault.
BTW, I'm not an armchair arborist. I'm a certified turf and tree care professional (still current, even though I'm out of the business) and I put myself through college caring for magnificent landscapes that included live oaks, St. Augustine and Bermuda grass.