Currently reading "Flying Blind", which was recommended on another recent Boeing thread. Not done yet, but I think it boils down to

- Boeing had a pretty strong engineering driven culture for a long time

- In the 90s, McDonnell Douglas bought Boeing with Boeing's money and McDD management took over, which was a mostly Jack Welch inspired bunch of value extraction types

- Engineering culture started decaying, drastic cost cutting, outsourcing and value extraction started taking place, with Boeing spending up to 80% of free cash on stock buybacks instead of investments

- Dreamliner program started in the early 2000s, 737 MAX several years later

I think it boils down to the erosion of the company not having progressed as far when the Dreamliner was being designed