There are some really interesting videos in the People Mover thread of the loop in the late 80s. The stretch from Cadillac Center to Times Square looks AWFUL - nothing on the Crowley/Kerns site, vacant Hudson's, almost nothing occupied on Library or Broadway, no Opera House, and almost nothing occupied on Grand Circus.
We've made huge strides, and if everything planned in that part of town comes to fruition [[Hudson's site, Metropolitan, Wurlitzer, Statler site), that stretch will be a fully functioning big city neighborhood again.
Bookmarks