yes, there may be exceptions. very, very few though. and yes they do fall well short of great glass.
I agree you can form some opinion based on the pedigree of the glass, I do the same. There are exceptions, though, but even these exceptions fall short of pro level glass.
the examples you;re citing are L glass, (pro grade). they were always meant for the pro market and so will always be great glass, relatively speaking. a nikkor 85/1.4 is pretty old but its exceptional in performance. its also not $300, nor is it a 5x zoom. name me an exceptional lens that is a 5x zoom you cna buy for $300. i'll buy it in a heartbeat.
I disagree that age makes any difference. The older FD L lenses from Canon are still excellent pieces of glass, and my favorite, arguably my sharpest lens is the old Canon 80-200 f/2.8L Magic Drainpipe. I also had a hard time deciding between the 28-70 f/2.8L and the 24-105 f/4L. I went with the latter, but the newer 24-70 f/2.8L wasn't even in the running, because the older 28-70 was regarded as sharper glass.