The Brewers are gambling whether or not they push the chips for a Skubal trade so it's not like they aren't still trying they're just placing different wagers.
To me the only way a big pay to get Skubal is worth it is by winning the WS. All or nothing doesn't feel like a smart move. That's not to say that there isn't a way to get Skubal and not have it be the big pay that I fear. It's all just unknown right now. You have a level of risk you're comfortable with and I have my own.
The rest of this is just rambling thoughts... feel free to stop here lol.
I think of the Bucks a lot in this scenario. Thank god they won a championship. I can not imagine the pain of doing all the things they've done and to have gotten to the point they got to this off season and not have that championship. I already checked out on them before last season their future looked so bad, there's a little hope there now but it's going to be a long road.
I don't think the Brewers are really close to that even if they did a really stupid trade but if they get reckless and don't make it it can be devastating, not just in the present but in the future.
The other problem with the "go for it no matter what" mentality is that it comes back again the next season, and the next season, and the next season. Fans don't care if it worked or not they want you to do the thing, especially if you did the thing last season why not do it again? It's sure to work this time right?