It's really not apples and oranges. It's a simple analogy to show that recent results, in almost every walk of life, tends to carry more weight as time goes on than results way in the past. It's why coaches get fired eventually even if they have early success. It's why GMs get fired eventually even if they have early success.
You are conflating things here as well because you struggle to admit Jerry has been a poor steward of the football operations in recent years. Separate Jerry the business owner of the Cowboys from Jerry the director of football operations. Jerry is clearly a shrewd business person, having made money in a variety of industries. He's also a master marketer having had the ability to tap into the popularity and culture of the Cowboys. There is no question that he's a fantastic owner from a business sense. It's why he's in the Hall of Fame. You could argue no owner has shaped the business side of the NFL more than Jerry over the last 30 years.
He's most certainly not in the Hall of Fame for his GM skills, however. Jerry Jones (and his kid) have run football operations since Jimmy left. Since the last SB with a team Jerry and Jimmy built, 25 years have gone by and over that period, they have 4 playoff wins total. Yes, you read that right. In 25 years since their last SB, they have won only 4 playoff games. They are one of like 6-8 teams in the entire NFL who have not even played in a conference title game over that same period. What GM in the NFL would survive that kind of run? No one would.
You made this statement:
It's really not the last couple of years. It's been 25 years as I noted above. The franchise has not won a thing since 1995. He's had sole control of all things on the football side of the franchise over that period. Further, the Cowboys lack of any sound, rational plan in FA other than be real cheap has come into play more in recent years as Stephen as become more involved. There was a time when Jerry might throw a dumb contract at a FA but he no longer does that largely because Stephen has sold him on the idea that spending in FA doesn't work. This has been evident since the Brandon Carr contract.
The problem is these have operated on the edges. They went from Jerry spending like an idiot in FA to Jerry not spending any real money. There is a huge gap between spending like a fool in FA and not spending much at all and the Cowboys seem intent on ignoring it.
And it shows in their recent results. For while they draft better than average, their teams are clearly flawed year to year because they simply fail to acknowledge holes or overvalue their ability to find cheap options to fill those holes adequately. Look back at their free agent signings over the last 5 years. Very few, if any, have really made any real impact. And it shows on the field as the team has continually underperformed and been let down by clear holes that they refused to try to fill (mostly on defense over the years) with good players.
PS - Where did you pull this idea that he's one of the most respected GMs in football?