re: Are you surprised that the New York Yankees are stuck with 27 World Championships in 2018?

2000 is when the spending really started, prior to that their moves were smart. Grabbing Paul O'Neil from the Reds, David Cone from the Jays, signing David Wells, they didn't make too many splashes. However, 2000 things changed and they went after players who were close to 30 hitting their first new contract and subsequently started to decline after 3 years.
Most of the payroll prior to 2000 stemmed from resigning players that came up through the system such as Bernie Williams or players that came on slick trades such as Paul/Cone.