I agree, I think the only real hope for Griffin playing on the same team as Skenes is if he's a true phenom and does something like surge up through the minors by the end of next year. Even then it might be pushing it a bit, as we are already seeing random talk about trading Skenes now (I'd dismiss it, but it's just gonna get louder into the offseason and next summer).
The only outside the box possibility would be if the current 100-loss team leads to some kind of quick strip down which is then re-allocated into Skenes and Cruz somehow, but it obviously seems like a stretch to even raise that. Setting Cruz aside for the moment, the only real way I can see it with Skenes is if we were to sign him to some kind of cost-secure deal for his arbitration years.
Outside of injury risk, he really has little reason to do it, but given that the costs are easy enough to ballpark with some certainty, there may be reason on both sides to do it, if and only if the Pirates were able to come to the table. He's controllable through 2029. He will be the highest paid pitcher in arbitration, but those are still costs that could be "stomachable" for a team cutting all corners and never rising to a competitive payroll (i.e., if Keller and/or Reynolds have to be gone by the time it would kick in).
It goes without saying that Skenes has no reason to include any years beyond 2029 into the equation of an extension, which is why I think this outside the box possibility is mostly an exercise in futility. The Pirates would surely want that, though whether in that case or not, there's pretty good reason to wonder if they'd actually pay the "high dollar" years on any contract (Keller's impending departure, which I wouldn't be shocked to see happen this summer, points in that direction).
In any case, if somehow they could get the extension done, maybe it would be with a kind of massive mutual option for 2030 or something. In terms of what it would mean for the Pirates, it would at least "buy" some time of 2026, 2027, and maybe part of 2028 before the inevitable trade would be in the works.
All of that makes the completely and totally wasted 2025 that much more frustrating, and -- I'm glad to admit it now -- makes the promotion at this time last summer look stupid. I know I was maybe the loudest person about him being ready and to not play games with service time, but given the clusterf*** of this year, it now looks like you have Skenes for sure for 2026, and starting that offseason and into next summer is when you entertain the "franchise-altering" trade package for him (spoiler alert: it will alter nothing, even if it's a Soto-like package).
It's reason enough to figure that we "have" to play those games with Chandler, given that the obvious logic is that we'll get a year or two of overlap between them with the "window" being times more with a Chandler + Griffin headed team than the guy who will be the best pitcher in this generation who fell into our lap.