Some kind of Cruz extension would change the dynamic of the ownership narrative, IMO. There's definitely some risk involved in any kind of lengthy extension, such that I think for that and others reason, it won't happen, but the excitement of a young player who storms on the scene and then is made into a face of the franchise in short order is how you get people everywhere to shut up about you being a farm team for their stars.
The nature of any contract would be hard to predict because of his current age, as people have already mentioned. If he's 20 or 21, then based on the standard way people look at things, you have to do some kind of contract in order to get prime years of the age 26/27 seasons. As it stands right now, that's Arb 1 and Arb 2 for him, and while those could get expensive if everything starts clicking for him, it's still not going to break the bank entirely.
From the Pirates perspective, a big contract this offseason would be the best time to do it, since the two additional TC, league minimum years give you a fair amount of leverage. I think they are very risk adverse but also that longer contracts early in players' careers tend to favor the team pretty strongly. In the end, I am pretty skeptical that we'll make a serious attempt, but I think the most optimistic thing we might try to do is gauge his interest on a 7 year deal in the offseason. That would buy out two FA years and also coincide with the final guaranteed year of Hayes' contract (2030). I'm not sure it would be enough to lure Cruz, but there is some upside to pretty enormous raises over league minimum for two years, I would think.
This is obviously a loaded comparison to reach for, but if Cruz took that kind of contact, he would hit free agency at the same age that Judge is going to hit free agency. If he's a regular 35+ HR guy, he's still got potential for a second big contract, and his value only levels off some if he ends up becoming a DH or just gets hurt. I think he's too athletic to become a DH, even if he moves off shortstop as he approaches his late 20s. There are also a lot of ways that a player never hits free agency in the right way, so I see a guaranteed contact as potentially appealing to him, but it has seemed like the Pirates move slowly with these kinds of decisions. I'd like to be pleasantly surprised, but I bet after just three months of a rookie year, we'll try to engage with a bargain offer and see what happens. Maybe things get really weird if he does something ridiculous like pushes for 20-25 HRs, which I don't think is as insane as it sounds if his contact rate keeps inching up, but ultimately I struggle to see it happen.
For me, the bare minimum bar this winter is seriously approaching Reynolds and getting his contract situation under control. There is no strategic upside to entering next spring training without an extension worked out, because at that point it would have been better to deal him already, and not just at the 2022 winter meetings, but probably at the 2021 deadline. The alternative is tension-laden arbitration meetings for two years and trade rumors, which didn't seem to be great for him. They could play it out and then give him the qualifying offer eventually, but the better path would be to just commit to him as a building block and then get some better supplementary talent in for the immediate future as a bridge to Davis, Priester, and anyone else who might be able to help in 2023.
