With Dave Dombrowski out and a new baseball operations guru presumably on the way in, the Red Sox are approaching a critical juncture. Chief among the priorities of Boston's revamped front office will be dealing with 2018 AL MVP Mookie Betts, which could mean dealing Mookie Betts ahead of his contract year or trying to build one last team around him before he becomes a coveted free agent.

The question is simple, the answer is not: Should the Red Sox trade Mookie Betts this winter?

Tom Verducci

The Red Sox should explore the trade market for Mookie Betts immediately after the season–before the free agent market starts to percolate. That doesn't mean he should be moved at any cost. And the value of one year of a star position player isn't as great as you might think it should be. But Boston hasn't gained any traction on an extension, so it would be prudent to see if a good deal could be made. If not? Announce you're keeping Mookie through 2020 and playing it out. Don't let trade talks of a star player linger.

Emma Baccellieri

No. There'll be reasonable pressure for action after this disappointing season (beyond the dismissal of Dave Dombrowski) and this particular move could seem attractive; Betts doesn't seem interested in a contract extension and carries a $20 million annual salary—which will almost certainly increase after this winter's arbitration—on a team that's reportedly interested in getting under the luxury-tax threshold.

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But he's also Mookie Betts. Sure, he'd yield a hefty return. But he'd also create an enormous loss for a club that's ostensibly still trying to contend for the World Series in 2020, not to mention a potentially awful public relations scenario. The Red Sox are not backed into a corner here. They don't need to blow their situation up. There are plenty of ways to upgrade the team that don't involve trading Betts, and doing so could create more problems than it solves.

Jon Tayler

No. The Red Sox aren’t a team that needs to tear it down, which is what trading Betts would signal. The core is strong, and the window of contention is still open. Giving up Betts is giving up, period. But on top of that, there’s no team that’s going to give up the ransom of prospects necessary to make a Betts trade worth it. With only a year to go until free agency and most contenders unwilling to spend their prospect capital for anything other than young players with lots of team control left, Betts’ market likely wouldn’t be all that strong. Boston should run it back one more time with Mookie, then let the chips fall where they may—bet on Betts, as it were.

Connor Grossman

I'm all for transactional chaos. That's part of what makes the NBA so entertaining to follow. But the Red Sox going out of their way to trade a supremely talented player such as Betts is hard to justify. Why trade a sure thing for a grab bag of pieces? As Tom notes above, Boston should explore a trade of the former MVP this offseason. Anything short of a slam-dunk opportunity however, should be turned down so the team can field its best lineup in 2020.

Matt Martell

The Red Sox should only trade Mookie Betts if J.D. Martinez doesn't opt out. I don't think the Boston fanbase can buy into a complete rebuild, and I don't think the team should do a full teardown, so the franchise can't lose both Betts and Martinez. If Martinez stays, the Red Sox should flip Betts for young, controllable talent. If Martinez leaves, then they keep Betts, try to get under the luxury tax, and hope their pitching staff that they invested in heavily gets healthy. It's still a talented roster without one of the two stars, but Boston becomes a lot less competitive without both of them.

Michael Shapiro

Have the Red Sox completely forgotten 2018? We're not even a full year removed from Betts's MVP season, a completely dominant campaign in which he led the AL in runs, batting average and slugging before Boston won its fourth World Series this century. Betts plays a premium position and is just 26. Boston has plenty of holes on its roster (namely its leaking pitching staff), though dealing Betts won't necessarily solve the issues. The seats at Fenway will stay pretty packed even if Boston goes through a brief title “drought,” and the revenue will continue to line John Henry's pockets. Even if a brief downturn is ahead, dealing Betts isn't close to the solution.