I am saying this now...if Rupp doesn't go 2:07 or lower at Chicago, he never will. Flat course. Weather is looking really good. Good competition. Marathon experience. Healthy (as far as we know).
Look at his 3 marathons: LA Marathon was hot. Rio was hot and humid. Boston is not known to be a fast course. This is his best chance so far to lay down a "real" fast time.
Running fast is nice, but isn't the goal of a "race" to win it? And if not, to place as high as you can? Fast times are nice, but when I'm in (or should I say "was in"), my goal was to win it. if a fast time is what it took, all the better.