I dunno, what's worse.....never winning a Super Bowl or winning one so long ago that you can still remember what it felt like?
I think the greatest disappointment isn't the fact that it has been 30 years. For me, the greatest disappointment was the fact that the Cowboys had placed themselves in a position where they had a strong enough team to contend and got brushed aside early.
This happened on several occasions. The Cowboys were strong enough to go deep in 2009, 2014, 2016, 2019, 2021, and 2023.
Those teams were positioned just as well as the teams in the 70's and even 90's.
In some cases, they were the 1st or 2nd seed. You can't expect them to "seize the moment" every time but you shouldn't be disappointed every time.
At the very least there should have been a couple of times where they made it to the conference championship game.
In 1980 the Cowboys reached the NFC championship game with the 17th ranked defense. They went to the NFC championship game again the following season with the 20th ranked defense.
There have been four occasions in Cowboys history where they had the #1 offense in both scoring and yardage. Two of them have been in the last five years.
There have been 16 seasons in Cowboys history in which they were a top 3 team in point differential.
5 - Cowboys won the SB
1 - Lost the SB
5 - Lost conference championship
3 - Lost division playoff game
2 - Lost wildcard game
The two most recent, 2021 and 2023, they lost the wildcard game.
We can't blame the quarterbacks for this. None of them have been 30-year starters. This is failure at the very top.
At least other teams have the luxury of purging their incompetent management teams and going in a different direction. We have to pray that, someday, the Cowboys owner will draw the same conclusion as that of 99.9% of NFL fans and media.
I do mean "pray" because that would take a miracle.