When he left is when the rot set in.
Leadeship got very top heavy - look at a masthead from the late 90's and see the ratio of VP to worker bees.
They bought up McMullen/Argus and Dobbs to try to monopolize ad pages and set the price but none of the subscriber math worked, cost per thousand was insane. The hell of it was, the pubs were fine before the buyout, which was undertaken at a very steep price but financed with what was functionally junk debt.
This was a very bad, no good thing to do in the dawn of digital. They did it to themselves.