The problem is, there is no anchor store to lure shoppers downtown. Regardless of how many stores that nobody's heard of go into the Kresge Building, they will not draw nearly enough people to stay open on their own.
Hudson's was profitable up until the day it closed, meaning that it was drawing enough shoppers down there to pay the bills, and in that enormous building, that is quite a feat. If Macy's were to open in the former Hudson's location, they would draw in shoppers, and many of the empty storefronts on Woodward would see tenants.
I do agree with you that bars are not the way to fill up the area. People are only going to drive so far to get drunk and drive home, and downtown probably is further than most want to drive. I have seen quite a few pictures lately of Woodward in the 40s and 50s, and it is packed full of people in front of Hudson's, even in a photo from 1980, there are alot of people at Hudson's around noon.
The problem is not many people are going to drive downtown to go to stores they have never heard of, when they have those a lot closer to home. People are going to come downtown because of the name, and a Macy's store would certainly bring a worthwhile name to downtown. Just look at malls. How many malls survive without an anchor store? Not many. Livonia mall, for example, started losing anchor stores in the late 90s early 2000s, and now the mall is gone. It is the anchor stores that draw people, and the rest of the stores will follow.
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