Chaim Bloom isn't a quick-fix kind of guy. His meticulous attention to process and ability to take the long view made him attractive when the Red Sox revamped their baseball operations department in 2019, and those very same qualities have helped him maintain the confidence of ownership despite a disappointing 2022.
The looming offseason is filled with peril, however, and if the Red Sox hope to contend next year, it's going to take one hell of a winter makeover that will require Bloom to step out of his cautious comfort zone.
"Daunting" doesn't even begin to describe the task.
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Forget about building a championship roster -- the Red Sox will need to extend themselves just to field a representative team. As things stand now, only four offensive starters remain under contract for next season: second baseman Trevor Story, third baseman Rafael Devers, left fielder Alex Verdugo, and catcher Reese McGuire, who's technically a career backup. If you want to throw in veteran first baseman Eric Hosmer, that's five, but he's a candidate to be moved, especially with the Padres basically paying the remainder of his salary.
The pitching staff is equally ill-defined. The only guaranteed starters are Chris Sale (gulp), Nick Pivetta, and Brayan Bello. The only surefire relievers are Matt Barnes (again, gulp) and John Schreiber, with Tanner Houck and Garrett Whitlock factoring into one unit or the other. There will probably be a home for Kutter Crawford, too.
That means the Red Sox will enter the offseason potentially in the market for a first baseman, middle infielder, two outfielders, and a DH. They'll need at least two starters no matter what they do with Houck and Whitlock, and potentially as many as five relievers.
That is, quite frankly, insane. No one wants to build an entire roster in one winter, even a team like the Red Sox that projects to have about $140 million to spend under the $233 million luxury tax threshold. That's an exercise in futility, because the odds of hitting on that many players are low.
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And yet, in an interview with The Athletic, Red Sox CEO Sam Kennedy said he believes the turnaround could be swift.
Kennedy insists Cora and Bloom will be back with Red Sox in 2023
"To be looking up at the American League East at this point of the year is painful and frustrating," he said. "And frankly we deserve the criticism we're getting. We've got to own that. It's on us. But we've been around here a long time and we're prepared to turn things around quickly here as we head into '23."
That's easier said than done, especially in a division with the Orioles already pushing for a playoff spot despite barely dipping into baseball's best farm system. Catcher Adley Rutschman is only the start of Baltimore's talent wave. And we're not even mentioning the Yankees, Rays, and Blue Jays, who'd all be playoff-bound if the season ended today.
The Red Sox, meanwhile, may be able to fill first base with prospect Triston Casas. They can surely find a home for the oft-injured Christian Arroyo, a tantalizing offensive talent who has yet to prove he can play every day. Maybe they find a way to re-sign shortstop Xander Bogaerts if his market doesn't materialize elsewhere.
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That still leaves two massive holes in the outfield and at DH, and I suspect the Red Sox may target Yankees outfielder Aaron Judge, an insane offensive talent who's probably going to win the AL MVP award, but who nonetheless turns 31 in April and hasn't exactly been a model of durability during his seven seasons in pinstripes.
Judge declined a seven-year, $213.5 million extension offer in April, and his current production could push his ask over $300 million. That would be a massive risk for any team, but the Red Sox could be tempted not just for the talent, but the opportunity to steal a star from their rivals while also countering the narrative that they no longer wish to spend. While Judge isn't Hanley Ramirez or Pablo Sandoval, PR is still a bad reason to sign anyone.
The pitching staff offers its own drama. If free agency has taught us anything, it's that starters in their 30s make bad investments. That would seemingly rule out the pursuit of Mets Cy Young Award winner Jacob deGrom, though recent elbow and shoulder injuries could leave him looking at a short-term deal that might be more palatable to Bloom.
Maybe the Red Sox offer Nathan Eovaldi a qualifying offer and he accepts. Perhaps they attempt to retain free agent Michael Wacha. Either way, the starting staff can't afford another season of Josh Winckowski, Connor Seabold, and other internal candidates soaking up starts.
The bullpen needs a total makeover, as evidenced by the recent designations of Hirokazu Sawamura and Austin Davis, as well as the deadline trade of Jake Diekman and the continued struggles of Ryan Brasier. The two best returning arms are probably Whitlock and Houck, but given the dearth of starting options internally or on the market, they might both best be utilized in the rotation, as damaging as that would be to the later innings.
Bullpen help is cheaper and easier to find than good starters. This feels like one of those choices with only wrong answers.
It's hard to remember a Red Sox team that entered an offseason with more needs across the roster, and we didn't even mention the challenge of signing Devers to a long-term extension. Fixing those issues won't happen overnight, which means we should prepare for the possibility that the Red Sox are even worse at this time next year than right now.