My issue is, the "what ifs" can be played in both directions. Not just what if the prospects we get for Joe Ryan turn out to be Kohl Stewarts, but what if having Joe Ryan on the Twins leads to a 90+ win 2027 squad that has a decent chance to come out of the AL?
What if trading him now prevents that? What if we trade Joe Ryan and this time next year we aren't quite good enough to go for it and we start doing the "future value" math on Taj? Well... you know,,, he's down to 2.5 years of team control and he's getting expensive. Should we maximize his value? We could probably get some good prospects
What if we hadn't traded Duran and Varland last year? What if having them on the team this year instead of the contributions of Abel, Rojas, and Roden would've meant we were 5 games better? Maybe then we're buyers and rather than worrying about adding bullpen depth, we're looking at one big SP move that's going to move us up a notch in the AL power rankings?
What if the mindset of being a seller every year in an effort to permanently maximize value turns into a search for a future competitive team that never comes? The "go for it" team never arrives because past selloffs have hamstrung teams that maybe otherwise could have gone for it.