When Jimmy Johnson left that was the beginning of the ongoing lengthy drought. Of course, he won another SB with Jimmy Johnsons Team but with Barry Switzer as the HC.
But when Jerry basically said in a Presser back then, he could have just about any HC coach the Cowboys to Win a SB.

That basically was the beginning of the end. I remember when they had like 3-4 straight yrs of 5-11 Teams he had them hyped up as SB Teams lol!

Well, his cryboys and the whiners have been greatly affected by the Free Agency and Cap Era when they both flourished prior to that. The Free Agency and Cap Era was mainly brought about to not have Teams like the whiners and cryboys be Powerhouses yr in and yr out and tip the talent scales. GO RAMS1