One of the problems with Reinsdorf is he is a long time owner.
I'm not sure of any other current hands-on owners have been around for 40 years. In the 80s, major league baseball was still fresh with the memory of an actual franchise bankruptcy in the seattle pilots. League health was a real concern, and even worse in his other franchise the NBA. Your location was everything. Jerry bought into the white sox as a baseball franchise, but was also buying into the MLB.
And 40 years later I'm sure a lot of the ridiculous work he did to shore up the MLB leads to today's game. Your location is not near as important as it once was. National revenues, MLBAM at one point, and revenue sharing give every franchise an easy floor. Basic new owners are buying fun toys that may lose them some cash in any given year but have a steady appreciating asset that makes it no high-stakes purchase that will dent their wealth. Look no further than the LA dodgers sale earlier this decade, used and abused by a ridiculous owner in dire financial straights and divorce, forced to sell, somehow breaks all records and sells for 4 billion. Smart new owners are realizing they can use the power of the local popularity of sports teams to add layers of commerce and retail around their stadium like LIberty Media has done.
But Jerry's focus has, since the mid-80s, prioritized "league health" (/sarcasm) over his own franchises competitive edge. He'll collude with other owners to keep salaries down. He'll go hard against the union and destroy one of his teams best chance at a world series and cancel a season. He'll refuse to let his org set markets on player contracts. He'll dictate to his org that they must not go over the recommended slot bonuses for the mlb draft. He won't let his team go big on international market until the new system was set, while, for instance, today's Rays were built on an incredible haul in 2014.
And an owner whose teeth were cut seeing franchises actually get in trouble by overpaying for unproductive talent knows you don't overpay for 16 year olds. Stay out of that game. Millions for a high schooler? Remember Kris Honel? No, no, the game is won by ignoring the trends and just focusing on getting those tried and true productive players at your price.
It's possible the league enters a different place at some point. That sports is no longer the holy grail of live viewing and gets split to death like all other content. And maybe then the current owners will turn to the wisdom of a JR.
But instead it's just sox fans paying the price for an extremely outdated owner who is extremely arrogant about how excess can lead to pain for a franchise. Whose pain? Well the owners pain. Not really the fans.