Oak Hollow Mall came to be in 1995 which, even if you figure that the Triad is generally five years behind the rest of the nation, is pretty late in the game for a shopping mall.When it comes to High Point politics, this really rings true because there's a real generational lag. When downtown was at a crossroads 20 years ago following the defections of Sears and Chick-Fil-A to the mall, the Silent Generation was still firmly in control of High Point politics--even though the nation as a whole witnessed Baby Boomers replacing Silents in positions of authority. So, the planners must have been a '60s/70s mindset of focusing on the suburban areas while abandoning the center city when they let the furniture makers have downtown all to themselves (it's worth noting that 1995 was about the time that Rust Belt cities began their revivals, and downtown revivals took off about 5-10 years after that).
After all, it was only in 2012 that the city elected its first Boomer as mayor after 20 years of Becky Smothers and Arnold Koonce. Even though the current city council is 2/3 Xers, Boomers still control the overall political infrastructure so it's no surprise to me that Milennials are going to Greensboro after the movers and shakers have openly discouraged them.