We all know spending is everything, and the beef over JH's spending is legit, but over all he's spent more than most teams every year. He's spent more than 2/3 maybe all but 1-2 years. He's spent more than 3/4 over half the seasons he's been at the top. The next guy may or may not come close to this.
On his choices of who will run the show, it's a much bigger mixed bag, and the way he handles the transitions has been a clear disaster. The guy has many faults. He may have gotten lucky with Epstein (9 seasons) and DD (4 seasons.) Manny feel the ring under Ben's watch was lucky, but overall he's had a decent to great leader for about half his time with the Sox. Maybe the next owner could do that well or better- maybe not.
The disfunction since 2019 has been well documented and discussed, and making the playoffs twice in those 7 years has been little solace to Sox Nation. For many of us older fans, 7 years pales to the decades upon decades of incompetent leadership and uncaring to even racist owners, but it just seemed like those years it was more fun to watch. Maybe it was our youth, or maybe it's just more fun watching teams mash and lose vs teams that can't hit their way out of a wet paper bag.
Our .411 winning % is dangerously close to 2020's .400. When you consider how bad the rest of the AL is, it makes it worse than 2020. To me, what makes this worse is that I felt like we were getting better and had a decent foundation of young players and promising prospects. We seemed like we were just 3-4 key pieces away from being serious contenders. Looking at Contreras, Suarez and Gray, it seems like those were better winter additions than we've seen in a very long time and at least since pre-2019. It seems baffling that we got this much worse.
Many of the suggestions we all had over the winter wouldn't have mattered, either. It seems obvious, now, that the "foundation" was not as good as we thought, and we needed more than we thought we did. It wasn't Cora. It wasn't Devers. It was much more.
Every team has injuries, and living here near Houston, I am witness to an Astros team that blows everyone else away on that front, and yet they keep winning more than us while also losing its best players to free agency year-after-year.
Rolling the dice on new ownership clearly appeals to the vast majority of Sox fans, but doing so vs no doing so both seem like losing or highly suspect choices to me.