Forget about the end of the honeymoon period -- Chaim Bloom could be served divorce papers.
Baseball's winter meetings open Sunday in San Diego, and the chief baseball officer of the Red Sox is the man under the microscope. Now entering his fourth full season, Bloom oversees a last-place roster with a staggering number of holes and only one winter to fill them.
Red Sox ownership has a tendency to back its general managers right up until the day it fires them, and Bloom is already nearing the expiration dates of predecessors Dave Dombrowski (four years) and Ben Cherington (three-plus years). Not even a World Series title could save either of them.
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All Bloom can hang his hat on is a run to the American League Championship Series in 2021 that screams "outlier." In many ways, the team's rebuild is just beginning, which is a precarious position for a fourth-year executive in a major market to find himself.
With Bloom focused on strengthening the farm, the big-league roster has suffered, and he's running out of time to fix it. Waiting out the market will not work this winter, not with the Red Sox hemorrhaging high-end talent.
The stakes for Bloom couldn't be higher. His job may very well hinge on how he handles the next three months. Here are five things to watch as the meetings begin and the offseason kicks into overdrive.
1. Does anyone want the Red Sox?
Of all the free agency developments so far, the most shocking is this -- the Red Sox aren't a destination.
Two free agents have already spurned them. First, former White Sox slugger and clear Red Sox priority Jose Abreu signed a three-year, $60 million deal with the champion Astros. Then right-hander Zach Eflin shopped Boston's three-year offer to the Rays and took the same money ($40 million) to play closer to his Florida home, per multiple reports.
The Red Sox have never struggled to attract talent, which makes it so jarring to see someone decide he'd rather play for the Rays. It suggests that if Bloom identifies a target, he's going to have to pay more than he'd like just to get in the door.
This is what happens when you're a last-place team in a loaded division. Players who prioritize winning look elsewhere. Red Sox ownership can't love that.
2. The Trea Turner market
It's clear that a number of teams in the market for a shortstop consider Turner the star of the class. This is relevant to the Red Sox not because they're likely to sign him, but because of the way it will impact Xander Bogaerts.
The Red Sox have proclaimed Bogaerts their No. 1 priority, a regrettable declaration that feels doomed to become a punchline. The clubs aggressively in the market for a shortstop -- Phillies, Dodgers, Cubs, Padres -- can't all sign Turner, and many view Bogaerts as their Plan B.
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Imagine a bidding war between the Padres and Phillies for Turner. The loser could immediately pivot to Bogaerts, with their spending muscles already flexed. There's some debate over whether Bogaerts would give the Red Sox a last chance to match, but it certainly feels like that ship left port sometime in April when Bloom lowballed the proud star.
It's doubtful that Bogaerts is the first domino. But once Turner comes off the board, don't be surprised if Bogaerts quickly follows.
3. Rotation approach
The three-year offer to Eflin, who's basically a league-average starter, suggests the Red Sox are not in the market for a top-of-the-rotation arm. They've already watched the Rangers give former Mets ace Jacob deGrom $185 million, and they haven't been linked to Giants left-hander Carlos Rodon or Astros righty Justin Verlander.
Riding with Chris Sale, Nick Pivetta, Brayan Bello, Garrett Whitlock, and perhaps James Paxton feels extremely risky, and it's worrying that the Red Sox prioritized a pitcher like Eflin to bolster what was one of the AL's worst rotations.
If they remain in that middle area -- perhaps reuniting with Nathan Eovaldi -- it's hard to see how reliable their rotation will really be.
And that leads us to ...
4. Look for a run on relievers
The Red Sox have already signed former Mets lefty Joely Rodriguez, and they've reportedly reached agreement with ex-Dodgers right-hander Chris Martin on a two-year, $17.5 million contract.
While Rodriguez profiles as more of a low-leverage arm, the 36-year-old Martin is a legit late-innings weapon with strikeout stuff who doesn't walk anyone.
If the Red Sox want to build their pitching staff from the back forward, it's hard to argue the approach in today's game. The Astros, after all, just won a World Series with the best bullpen in baseball, a group so deep that veteran standouts Phil Maton and Will Smith didn't even make the initial postseason roster.
Outside of sidewinding right-hander John Schreiber, the Red Sox struggled to find reliable relievers all season. The Orioles are another example of a club that remained in contention based on their bullpen, and if the Red Sox want to hand out a bunch of two-year, $20 million deals, there's a chance they could revamp that weakness this winter, too.
5. Harvesting the farm
After four years of refusing to part with prospects, Bloom must start dealing from his surplus, since the team's needs cannot be filled in free agency alone. Dombrowski may have sold the farm, but he did an excellent job identifying keepers, and no one the Red Sox lost has really come back to haunt them.
Bloom probably won't trade top prospect Marcelo Mayer, but virtually everyone else should be on the table, especially with a tantalizing young outfielder like Pittsburgh's Bryan Reynolds reportedly seeking a trade.
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The Red Sox have hoarded prospects long enough. They missed their trade windows on Bobby Dalbec, Jarren Duran, and Jeter Downs. If Bloom wants to keep his job, he'll start parting with younger players to acquire the established ones that will be key to avoiding another last-place finish.