We have heard murmurs for almost a decade now about KW and Hahn allegedly telling Reinsdorf they thought the best course of action was to tear it down to some degree and instead having the owner encourage/demand they push for nearer-term victories. Who knows for sure about these things, it's impossible to verify. I do believe starting around 2012/2013, Hahn and/or KW did not want to push for a playoff run any longer because they thought it would be futile but Reinsdorf didn't have the appetite yet for anything that looked like intentional losing.
2012:
The 2012 season really screwed things up. That team wasn't good, didn't deserve to make the playoffs, but came very close to making it. You could tell what they thought of the team's chances by the way they sought to improve it mid-season: acquiring Orlando Hudson, Kevin Youkilis, Brett Myers, and Francisco Liriano. Even those moves ended up costing us some talent, especially Eduardo Escobar (hindsight is 20/20 of course), but there was a deliberate effort to appear to be trying once that team started winning but also avoiding a real earnest push to improve them. In the end, the team missed the playoffs due mostly to the fact the team was very lucky for much of the season and ultimately the lack of talent caught up with them.
2013:
But 2012 put the team in a position in which they could not tear down over that offseason. But they wisely invested nothing important in improving the team, either, ultimately doing nothing but making a half-assed effort at patching the gaping hole at 3B. We flushed $12M down the drain for him, but while I'm sure Reinsdorf still misses the money it had no real impact on the franchise because it wasn't as if Keppinger was supplanting some important young talent at 3B — we even decided to let Conor Gillaspie take a big portion of the reps there back when he looked like he might become a solid MLB regular. We see the writing on the wall and trade Peavy, Rios, and Thornton and in return get some familiar and less familiar faces.
post-2013:
In the offseason, we traded Hector Santiago and Brandon Jacobs (from the Thornton deal) for Adam Eaton. This is a fantastic trade, in my opinion. The Sox saw that fielding independent metrics for Santiago and sold high. Ultimately, I think Santiago showed that he was one of the rare birds who could consistently out-perform those metrics but he burned out relatively quickly anyway. Eaton made the team better both right away and in the future. We then traded Addison Reed for Matt Davidson. Reed ended up taking some lumps right away with the DBacks but recovered somewhat and then got very good again with the Mets. We lost this deal, but the limited value of a setup guy and the potential upside of Davidson makes me not upset about the deal — not every acquisition pans out. We also sign Jose Abreu, who was old for a prospect but just entering his prime and that deal showed us aggressively trying to infuse this team with young talent. That deal worked out very well too (even if you're disappointed that Abreu isn't "the best hitter on the planet" as some projected). I don't fault the Sox for signing a guy who was going to be good for at least 5 years and probably longer.
2014:
I have no complaints up to this point, really. Then...the 2014 season happens and we just don't do anything. The team sucks, we don't really make any trades, it just isn't clear what direction the team is going. There weren't really valuable veterans to trade so it wasn't like the lack of big action was a definitive sign of what we were doing. We had Sale/Quintana in the rotation and were still wishing on Danks. We had Abreu, Eaton, Avi (who gets hurt), Semien, Sanchez, and the last dance of Dayan. We had drafted Rodon and knew he'd be up soon. So we're doing okay but there wasn't really enough talent yet in the system to get us through the rebuild without some other moves. Our best options were to make some bold trades to really tear it down, stand pat and play the waiver wire game while we figure out what we have, or start signing some veteran free agents to try to cobble together a team that could back into the playoffs.
post-2014:
We went mostly with the signing veterans route: We bring in David Robertson, Zach Duke, Adam LaRoche, Melky Cabrera, Emilio Bonifacio, Matt Albers, and Geo Soto via free agency. Dan Jennings comes in via a nice little trade for Andre Rienzo. I'm of the opinion that sinking your MLB product solely for draft position is a stupid path so I don't care that we spent money on free agents since it didn't cost us any talent (and none of these deals had the potential to really harm the franchise long term if better players were needed).
We then made a very stupid trade that I hated the instant it happened: We get Jeff Samardzija in exchange for Marcus Semien, Chris Bassitt, and Josh Phegley. Samardzija had just one season before he would be a free agent while Semien and Bassitt were young players ready to start playing in MLB even if they were likely to need some time to develop (I never liked Phegley so I never cared that we dumped him). In Samardzija we got the league leader in hits, HR, and ER given up. Semien hasn't become a star but instantly became a 2-3 WAR player and someone who would have made that team better right away at any of 3 positions in the infield where we were abysmal all around. Hard to know what to think of losing Bassitt as he was good that year in MLB but also suffered a major arm injury that we may not have been able to prevent.
2015:
Bonifacio instantly flopped and we did not have the young talent prepared to take the infield reps we thought we'd get from him (we traded the MLB-ready talent away). Melky was always overrated and was just okay. LaRoche was terrible, almost surely worse than Dunn would have been if we had asked him out of retirement. Relievers were all fine. Soto was fine, though we probably had a little higher hopes. We also learned once and for all that one-time cornerstones Alexei and Danks were no longer MLB players. This team was like the 2005 team except where instead of everything from the offseason going right, everything goes wrong.
Our ability to compete was a mirage from the start as our good veteran acquisitions all had better reputations than their production warranted (Melky and Samardzija especially). But again, that I don't care about. The free agents were just money and I don't mind trying to win via some veteran free agent acquisitions; wasting money is a victimless crime. But the net loss associated with getting Samardzija pisses me off to this day. And while I don't mind getting the free agents, the total failures of Bonifacio and LaRoche are not positive signs.
post-2015:
What's a team to do at this point? We still didn't have much talent in the minors, especially as all of our young infielders (Sanchez, Micah Johnson, and Saladino) who played the previous year had done equally poorly. We had to let Samardzija walk because he played so badly and apparently clashed with our coaches/management. Our tradeable vets were few, but this was a time where you could have considered trading Abreu (but it would have been tough — this was following what we now know to be his worst season, but looked at the time could have been the start of a downward spiral) or Sale, who was a bona fide star. Quintana could have been traded but he was still so young and I think teams were still skeptical of his production. Nobody was going to trade talent for Melky or LaRoche.
We just spin the wheels, mostly. We sign Avila and Navarro at catcher. Navarro will suck but it's not the end of the world. We get Brett Lawrie in what I think was actually a pretty good deal (sending Zack Erwin and JB Wendelken). He was under team control and pretty good. He then played adequately for us, especially considering the performances of the players he was replacing. I don't blame the Sox for the kid going nuts in the offseason.
The Todd Frazier trade is emblematic of the approach I didn't like with Samardzija, though he wasn't a pending free agent and I wasn't a believer in either Trayce or Micah Johnson. Hindsight tells us we did sell high on those two (Trayce's value would peak about mid-season 2016 with the Dodgers). We knew then that the prize of that trade was Montas and we lucked out that he ended up getting hurt and not really producing up to this point. Perhaps we knew he would get hurt, but I don't know. Ultimately we didn't lose much here but it probably wasn't the right thing to do.
In a move not many paid attention to at the time, we'd also get Tommy Kahnle for Yency Almonte in a prospect-for-prospect deal.
2016:
I won't say much about this season other than our bargain-basement free agents didn't pan out and we had a major screw-up by trading Fernando Tatis, Jr. for James Shields. It irks me but I also know that most saw him as the second piece in that deal. Time will tell if Tatis Jr. becomes the star that many project, but we gained nothing by having Shields around so there's no way to say that this was smart or good even if it was reasonable to think at the time that Tatis wouldn't pan out like this. This, paired with losing Eduardo Escobar and Chris Devenski in the 2012 midseason deals, shows the perils of making "low risk" trades for veterans when you're trying to half-assedly build up the MLB club.
post-2016:
The fireworks begin. I don't have serious criticisms of these times.
Taking a deeper dive into the previous years makes me feel pretty strongly that the key assets traded at this time were never worth as much in previous years and we basically never wasted an asset of similar value by letting him play out his deal/allowing him to decline and trading him later in those times. The front office had several failures in their attempt to do the impossible thing of brute-forcing those early 2013-2016 teams into contention, but the only important ones were losing Semien/Bassitt/Montas/Tatis in trades. The only one of those guys currently producing in MLB is Semien, so it could be worse. The more I think about it, the more I wonder whether we would have been much better off now had we gone full-bore into a rebuild in 2013. We probably would have traded Sale for less, probably wouldn't have tried to go for a player MLB-ready like Eaton, and traded Quintana for much less.
In the span of time post-2013 or so, we also got a number of players/prospects in the draft and international FA and we generally did not trade them away, part of the reason for the depth we have in the system now.