Jerry was mostly cheap beyond the Fisk signing, just as he is now. They were never a consistently top half payroll team as they would have been under Debartolo. A few brief sports after the WS and when the new park opened. Even now, “all in” they are cheap beyond paying two managers to fulfill Jerry’s asinine fantasies.
The only Top MLB Contract they pursued was Belle, solely because Jerry wanted to spite his fellow owners. He ended up dumping him after the second year, a year after the white flag trade , once spite ran its course and cheap and stupid returned in vogue.
Hemond was replaced because Jerry wanted his guy, not Allyn/Veeck’s guy. So he and Dombrowski were purged, and Dombrowski travelled across America building multiple great clubs including the White Sox’ other nemesis (Detroit). Himes did great in the draft but was purged as well.
Now stuck with White Sox Gar Pax entering year nine with now end beyond Jerry’s departure in sight. Same with the Bulls until a few years after Michael Reinsdorf took over and they could finally purge Gar Pax with Jerry gone.
This. The dysfunctional organization starts at the top. Hang on to unqualified cheap cronies to run the show, don’t know how to or bother need to compete on the field to make money.
It’s why the Sox and Bears have floundered for decades, and the Bulls for two decades once the gift of Portland’s blunder (Sam Bowie), Pippen and Jackson were gleefully purged by JR/Krause, followed by two decades of Paxton, a lottery pick (Rose) away from complete and abysmal failure.
Same with the Blackhawks until Dollar Bill died, and the Cubs until the Tribune sold, competent baseball people were hired and the money spent.
Once Jerry is gone, hopefully things will change for the better as they have for the Bulls, whether the Reinsdorf’s keep the team or not.