1. “Baseball strategies were better in the 1990s” is a plan that might have worked in 2005. Coming out of the Steroid Era, only the start of the Moneyball era of GMs getting smarter, well before the Strikeout era we are in now. It is now well out of date.
2. Kenny Williams wasn’t the best GM in the sport, but he was pretty good. Aggressive strategy, employed some good people. It worked pretty well for years, until personality conflicts worked their way in. That may be a message about his later years, guys who he trusted when they had success became full of themselves and has no leadership from the owner.
3. I think we all know the Jerry Krause story. The Pippen trade was brilliance. Bringing in Phil was brilliance. Grant, Rodman. Some of the historically best moves ever in basketball. Dismantling the team so he could get more credit for rebuilding it was unchecked arrogance, and again Reinsdorf let it fester.
4. Jerry Reinsdorf bought a franchise that already had Michael Jordan. His story is very, very different without that one key detail.