That last concept always needs to be appended to any allegations that Reinsdorf wants to win, and assumptions that losing makes Reinsdorf miserable. It’s another form of the famous-to-me Cigar Aficionado quote about Reinsdorf’s m.o. from 1995: “Throughout the fall and winter, he was still driven by the dream: to create a World Series winner in a business climate that made sense to him.”
https://blogs.fangraphs.com/the-white-sox-are-getting-a-facelift-they-need-a-new-head/
Being in the AL Central is really a curse for us. Jerry (rightly) believes we can compete for division championships and playoffs every year by doing things exactly the way he has for 40+ years.
If we were in the AL East, we'd be in last place every year and be eliminated from the playoffs by Labor Day. That would be enough for Jerry to "consider" changing his approach. Now, he can keep trying to win "his way" with sycophants throughout the organization and pocketing tens of millions from international and gambling deals before we ever break Spring Training camp.