If Jerry Reinsdorf thought it was good business sense to try and save a few bucks in signing Manny Machado, he was horribly outmaneuvered. The aftereffects of this colossal failure are going to cost him much more than that.
By trying to get cute with contract wording and adding incentives instead of guaranteed money, he lost out. By being so public about being “all in”, they also enraged the majority of White Sox fans in the way they lost out. If, as Kenny Williams said, they were never willing to go to the $300 million, then they could never have considered themselves really in it.