Jerry already did win his way, so I am not sure why this is a talking point 30 years later.
He hired Barry and he won a Super Bowl with Jimmy's team. Jimmy even said in his latest book that Jerry was right. Any coach could have won with that team. Barry inherited a train running down the tracks and didn't wreck it. Jerry relinquished control to Parcells years ago and the team still didn't produce a single playoff win. Jerry is as less involved with football operations as he's been in awhile, and guess what - the team still isn't advancing to a NFCC either.
The facts are the Cowboys have had numerous chances to win since 1996, in varying forms or fashions. They had arguably one of the best teams in football in 2007 and 2016, had the Offensive Player of the Year in 2014, had the top defense in the league in 2009, had the league's leading rusher several times, had the best OL in football several times, etc. There is a mental hurdle in this organization from the top down that this team simply can't jump over. Whether or not that's even fixable, I don't know.
What can go wrong, does go wrong. Every time.