It helps that there were no real payroll limits back then. There was a ton of talk about how much money Manny was getting, but never much concern about it having an effect on who else the team was able to sign. And the freely available steroids made the back years of long contracts less likely to be a total waste.I don’t necessarily miss what you’re describing, but what I do miss is the days when I could just be excited about getting a new player - like I was when they signed Manny - instead of immediately switching into hyper-analytical mode, which always leads to this “yeah, but look at all those years and dollars!!!” mindset.
I was going to say that people would be aghast at the Manny deal nowadays, and I think that is true, but I also remember a lot of people saying they were against it at the time. And I've also noticed a growing segment of baseball fans who are in favor of teams spending more of their money these days. But I still think people would savage the 2023 equivalent of a Manny deal. "He doesn't play defense, going to be ugly when he turns 35!"
These days the contracts are so long, the CBT draft and IFA penalties so harsh, and aging curve so steep that every long contract looks terrible the moment it's signed.