Well I was just a peon when I worked there, so it’s not like that experience mattered in my decision.
And my view on extensions isn’t you are paying for past years. Hell, I would sign Holliday today and Gunnar is only a year into things.
The issue with the extensions is that you are already have the player(s) locked up for most of the years anyway. So, when you sign them to an extension, you are guaranteeing 7-9 years but really all you are gaining is 2-3 years. It’s a lot of money and guarantees for only a few years.
Now, the one thing that I have talked about that is important here is if you don’t extend them, do you look to trade them 1-2 years away from free agency because you don’t want to lose a talent like Gunnar, for example, for nothing. So, maybe the extension buys you a few additional years on top of what are already getting. OTOH, you may just decide to go for it with the player and lose them for nothing.
I guess you always have the option of going the Tatis route and go 14-15 years but I’m not sure of anyone who is advocating for that or would be ok with that.
As for your business decision point here..I think that’s probably the biggest reason you do it…because players like the commitment and the fans like the commitment and there is value to that.