I'm not to interested in relitigating old deadlines, but in general I have wanted to see more caution thrown to the wind by Huntington. Even accounting for his bad moves, when you factor in the bad luck, he's done a good job of strengthening the organization as a whole. That's one thing that's generally been lost in this up and down season - when the lows got intense, skeptics wanted to come in and say we'll lose 100 games, but in reality we're on track to be about a .500 team, and might underachieve that mark, or now with the hot streak, overachieve it enough to take a run at the WC spots, or with some luck and critical wins, compete for the division.
That's a good thing for avoiding disaster team scenarios and an organization that's mired in hopelessness forever, but the flipside is the danger of being mired in the hopelessness of mediocrity. Based on past behavior, I don't expect Huntington and company to be self-critical enough or draw the lesson that pushing more chips into the center might have been worth it, but I also do think that Huntington was involved in discussions for Price, for example, so I don't think there's absolutely no chance he'll get more aggressive if the situation dictates it.
What it would take for the situation to dictate it is probably a condensed run of some more good luck. As I laid out last night, if the Cubs drop their series to the Diamondbacks and Cardinals, and we keep piling up wins, we could be in a situation on trade deadline day where if we win 2 game vs the Cubs, we get to within 2 games of them, with still 8 games remaining in the schedule against them. That would truly be insane given the situation literally 14 days ago, but it's where we're at. IMO the strongest frame of reference for being critical of risk-adversedness is whenever there's a chance to take the division, because taking the division automatically gives you a genuine shot to make a run at the World Series.
In other words, deGrom or Archer would clearly have a big boost on winning a wild card, but in a sense, the dependable rotation isn't absolutely in need of a lights out starter in order to be able to have the sustained success over the 50ish post-deadline games. The need is stronger to have an imposing starter who will potentially pitch twice in a five game playoff series. When looking at making a big move, Taillon or Musgrove might be that kind of pitcher, but it's not certain. The questions Huntington would have to answer are 1) does he generally think that the whole team can keep up its good play for 50 more games? and 2) if so, can he find a way to mortgage some of the future to maximize the situation should the playoffs be made?
This final point might be more sloppy, but I think another factor in play is that the composition of the current team isn't as much in the air as some of the older, a little bit more patchwork teams. On the assumption that Meadows would be a key part of a blockbuster trade, the main questions going into next season would be surrounding Newman/Kang/SS, Cervelli's future at C, and if Dickerson should be extended vs Reynolds and others in the higher minors. Harrison is still locked in at 2B, even Freese is around as the backup corner IF and bat. Even guessing that Kuhl or someone would be involved, there's a bunch of depth at SP, and while the bullpen can always use some tinkering, there are several guys locked in place.
I think this is a far cry from older situations, where the timing always was a little off, and you had more holes to fill. At the end of the day, the way I look at it is whether or not you can pull off a deal with Meadows/Keller as the cornerstones, and two more good pieces that hurt, but aren't really disastrous for the 2018-2020ish window. I think you absolutely can, and that the deal would be largely predicated on the idea of losing an unknown in Keller for 2.5 years of one of the better pitchers in baseball (if we're talking about deGrom).
This is all pure speculation, but I'll become more irrationally attached to it if we get even more condensed good luck and can shave off some more games in the division. There's an immense difference between being 7 games out of the division and 2 games out, and if we get so lucky to find ourselves in the latter situation next Monday, Huntington should be more cavalier in trying to get us over the finish line, lest we end up going down to the wire and staring down a wild card matchup of Williams or Nova vs. Scherzer or Strasburg or something.