The worrisome Red Sox question with a potential scary answer originally appeared on NBC Sports Boston
When will the Red Sox be good again? For 30 years, that question could be answered on a range spanning from "immediately" to "soon."
The best a realist can manage now, however, is a mopped brow and worried shrug.
Never in my 27 years on this beat have I felt less confident in the team's direction. Under chief baseball officer Chaim Bloom, the Red Sox are planning for a future that could be glorious, or might never arrive.
Building through the farm system without a run of top-five picks isn't easy, unless you're the Dodgers. The Astros won a World Series by enduring a string of last-place finishes and hitting frequently enough atop the draft. So did the Cubs. So might the Orioles.
But building a sustainable winner requires more than a prospect pipeline. It either means spending big in free agency, like the Nationals did to land ace Max Scherzer, or swinging a blockbuster trade, like the one that brought former MVP Mookie Betts to the Dodgers.
Under Bloom, the Red Sox have so far shown little inclination to make either type of move. They've signed one marquee free agent to a market-value deal, and that's shortstop Trevor Story, whose injuries could easily make him a cautionary tale for anyone wanting to justify swimming in the shallower end of free agency.
There are literally zero examples of trading prospects for an impact veteran under Bloom, unless you count the two-month rental of Kyle Schwarber. Until the Red Sox deal a prospect they actually like -- in another organization, now would be the time to maximize the value of Nick Yorke, for instance -- we'll be left to wonder if they hope to assemble their next great team via a combination of prospect promotions, waiver wire additions, and short-term veteran free agents.
This is uncharted territory since the arrival of Dan Duquette in 1994. The Duke had the moribund Sox back in the playoffs by 1995 and boasting serious star power by 2000, when they added Manny Ramirez to a core that already included Nomar Garciaparra and Pedro Martinez.
Theo Epstein then built a juggernaut that won titles in 2004 and 2007 while falling just short in 2003 and 2008. He complained about ownership's insatiable desire to "feed the monster," but even when he pushed to build through youth like Dustin Pedroia, Jonathan Papelbon, and Jon Lester, he still found time to augment the roster with productive high-priced veterans like Keith Foulke, J.D. Drew, and Adrian Gonzalez.
His successor, Ben Cherington, hewed more closely to the build-from-within model, befitting his formative tenure as farm director, but he wasn't afraid to spend, even if it meant landing the occasional Pablo Sandoval. At least Cherington knew which prospects to keep, as his minor-league core of Xander Bogaerts, Betts, and Jackie Bradley Jr. formed the backbone of the 2018 title.
Dave Dombrowski won that one by treating the farm as a means to an end, trading pretty much any prospect who wasn't nailed down while building one of the greatest Red Sox teams ever. He was fired almost exactly four years ago, and all he has done since joining the Phillies is lead Philadelphia to last year's World Series, with another playoff berth likely this fall.
Bloom belongs to a different category of boss: cautious to a fault, never more concerned with today than tomorrow, determined to keep virtually every minor leaguer for as long as possible, because you can't K if you never swing big.
Maybe his approach will be justified when Marcelo Mayer hits it big and Roman Anthony is launching rockets as an everyday center fielder. Just as likely, however, is that Mayer turns into a solid but unspectacular big leaguer, and Anthony becomes Hunter Renfroe.
It could be five years before we know for sure what either of them are. In the meantime, that's a lot of baseball encompassing the rest of Rafael Devers' prime, but not much reassurance that better days will arrive anytime soon.