I'm of two minds about it. I do think there's something to the team not being any kind of destination for someone who has several options, but for most players I still think money talks in the end. For mid-tier players, there's a pretty thin line between cashing in and having a poor season that requires you to take a very cheap deal or worse, so it can't be too wise to leave guaranteed money on the table.
The bit about not pursuing multi-year free agents in the end is actually coming from reporting. I haven't seen Mackey say much about it, but Alex Stumpf certainly presented it that was when interviewed by the NS9 podcast guys the other day. Something to the effect of the Pirates backing off whenever negotiations got into a second year. Whether it would be the best move or not, I think you can look at someone like Wacha being available as a further indication of this. He's someone you could easily bet on over a two-year deal at a modest price of 10-11AAV and likely return value.
I do think some of it is also about how the overall market is reacting, which is also where I see the Pirates getting priced out. For example, Syndergaard only looks so so as a starter nowadays, but he got 8M from the Dodgers and I am sure he will be deployed very effectively as a 4-5IP starter type, and maybe they'll find a way for him to get beyond that. That's probably "too expensive" for what the Pirates are looking to do, but the fact of the matter is that for MLB teams, one year contracts are never bad ones and at least given where the Pirates payroll looks to be, that should still hold true for them.
The offseason has started to go in a predictable direction for us, but at least in terms of the goal to be decent enough to flirt with .500 for a while and finish with 70-75 wins instead of truly bottoming out, I think a veteran SP still goes a long way. We should be able to pay top dollar for one year to get those dependable innings from one of the remaining guys like Wacha, Cueto, or Kluber.
For my money, there are two primary and related criticisms of the front office/ownership right now:
1) The payroll remains arbitrarily low and the owner isn't putting his money where his mouth is regarding an increased payroll when the time is right. All MLB teams just got 30M checks for doing nothing at all, but even with some additions, the Pirates payroll is on track to creep up maybe 5-10M next year and all we really have to show for this offseason is an embarrassing public request for a trade from our best player. A move like adding Connor Joe might turn out to be a savvy, no risk way to boost the current roster a little bit, but both that and starting pitcher are areas where more money could have been spent on short term solutions.
2) If we set aside the arbitrarily low payroll for a minute, there are also questions about how Cherington allocated what little budget that he had this offseason. The early moves read like scrambling to fix an area that's been a disaster offensively, as we claimed Diaz, traded for Choi, and then signed Santana. Maybe Santana was the main target going into the offseason and we felt (rightly) like the other opportunities made too much sense to pass up, but once we had Choi, it stands to reason that if the budget was very thin, maybe we don't throw most of it at Santana.
I like Santana and the veteran leadership angle, but if the budget is really such an issue, then I think it's fair to wonder whether or not it would have made sense to take his money or Choi's money and put it together with Velasquez's or something and then you'd have enough for Manaea. This second line of criticism is lessened for me somewhat if we pony up for Wacha or Kluber, but I don't expect that to happen.
From the outside, I think you can actually look at the moves overall and conclude that they make a certain kind of sense given where things are realistically at right now. It's addressing the major problems with actual competent MLB players and trying to get a real step forward from 100-loss hell. The obvious problem is that no team should really be allowed to linger with the kind of extended tear-down and tank job that we did while rolling out churned waiver player after churned waiver player for multiple important roster spots. In other words, the bar is only as low as it is due to this obvious tanking and poor job in earlier seasons. I'll be glad to watch a more mediocre team that might have Connor Joe, Santana, Choi, and Andujar helping out, and that's better than VanMeter, Tom, etc etc., but that's also not saying much.