Being a Sox fan from 1970 to 2003 was tough. It was almost more heart-breaking to be so good and come close so many times than had we just stunk. I remember saying many times that we should go all out to win once, even if it was at the expense of being really bad for the next 9 years.
Once we won in 2004, I got spoiled and wanted more, more and MORE! I still do, but I no longer feel the urge to have to "win right now", if it feels like it's coming at the expense of winning in the future- and I don't mean just winning 85-90 games every year and barely making the playoffs here and there. I realize that sounds contradictory in some ways, but I think our core of young players and upcoming prospects makes us set up pretty well to seriously compete for a ring over the next 5 years. I even think that because the AL is so weak this year, we have a good shot at winning the AL pennant, and then anything can happen in the WS, even if it's against the snake-bitten Cubbies.
I want to win now.I think, so far, DD has balanced the now with the future pretty well. While I may disagree with most of his individual deals, his overall plan and execution have been okay. Had Carson Smith not gotten hurt and done as well as 2015, we'd be in first place right now, but blaming injuries is something every team can do. We've actually had less major injuries than other teams and other years.
I can see how after winning 3 rings since Henry's take-over has made winning a ring less desperate, I still think that's the ultimate goal for me. I hated finishing second to the Yanks for over 30 years.