Jerry self-revealed a lot about his weakness as a GM at his “State of the Cowboys” presser a few weeks ago. While choking back his crocodile tears, he confessed that he would rather have a “beautiful” positive view of things than have a skeptical view- here’s an exact quote:
“I've had a lot of people tell me, 'You're naive,' or say, 'He's naive.' Well, it's a beautiful world. ... It's a better world to be naive than to be skeptical and be negative all the time."
The sad truth is effective GMs have to have a worst case scenario eye for his team because that’s what it takes to build a roster. Having a rosy view is great in most things in life but not for a GM. THAT explains the last 25 years in a nutshell.