I feel like the longer he goes unsigned the more inclined I am to believe the Pirates are making a push at least. That’s based on nothing but gut feeling and probably false hope
I agree, including gut feeling/false hope. The most interesting aspect in all of this to me concerns the potential weighing of a guaranteed short-term deal for 3/90M or so vs the mediocre long-term offer from the White Sox. It could be the case that teams are too hesitant to commit to a player for so long at a premium, and so in that case, would you take the money or would you take the security?
If that speculation is true, I think that's where the Pirates would need to try and press their offer further. You have to view the later years of the contract as a strategic gamble. In the absolute worst case scenario, Machado's defense declines to just solid/above average at 3B, and he maintains good power numbers with less speed. I'm not sure his hit tool is elite, but I just can't see any scenario where he really becomes an albatross. In the worst of all situations, you might have to pay down a bit of the contract and find an AL suitor who needs power at both 3B and DH, which hurts any trade. But even that's a stretch, because he'd be 30 or so when this potential trade was taking shape.
I think if that's all true, you have to step up and give the security as a fallback, and hope it ends up as a three year deal with an out clause. Maybe you negotiate it so that it's an 8 year contract and has a mutual or club option for that final eighth year or something, so that you'd plan to have him for the three years of the window, and then either look to trade or opt out, and worst case, you have a pretty big contract of 4 years that you need to start shopping.
Because otherwise, if he's going to entertain a 3/90M offer from us or something, it's hard to imagine several other teams, most especially the Phillies, not matching it. The Phillies could work it so that they could get Harper long-term and Machado short-term. I don't think short-term is going to be enough for the Pirates - they would have to do the absolute shocker and give the long-term with high AAV, and either plan for a CBA opt-out, or take the leap of faith and figure out what to do in 2021 or 2022 with the remaining years.