I've been thinking a lot about the 2005 Red Sox in the last few days.
After the euphoria of 2004, Theo famously broke up the band, turning departing stars into excellent draft position, netting MLB regulars Ellsbury, Buchholz and Lowrie among their first five picks. The farm system was already primed with top prospects, like Ramirez, Pedroia, Youkilis, Papelbon, Sanchez and Lester.
The 2005 team made the playoffs, but hardly convincingly. But the step backward laid the groundwork for a much stronger club between 2007 and 2013 — The Age of Ellsbury, we might call it — in which the team made three ACLSes and won two World Series. Some of the prospects were dealt for veteran contributors, but this era of the club was built around a young core, and with better health (Ellsbury's ribs and collarbone, Pedroia's foot, Buchholz' shoulder/neck, Youkilis' back, Lowrie's everything, let alone Kalish and Westmoreland...) might well have made another deep playoff run in 2010-11. They probably lost 25+ WAR to injury between 2010-2012.
I think 2014 is another 2005. Cherington was right to retool rather than rebuilding last offseason, to get one more run out of this core, but that doesn't mean that is always the right move. This offseason he needs to avoid longterm commitments to aging veterans, and move towards a younger club. We have 9 or 10 potential top-100 prospects on the farm, and while not all of them will pan out, that looks like the basis for a young core that could keep this team reliably contending every year 2015-2020. A ton of them are pitchers. That's a good recipe: compare to what the Cardinals have done since their championship in 2011; they let Pujols walk, went young, and reached the NLCS and the WS in 2012 and 2013. Not bad. And with all of the young pitching coming up, they should contend for years.