Red Sox: Boston must address outfield issues before 2021 free agency

BOSTON, MA - APRIL 12: Jackie Bradley Jr. #19 of the Boston Red Sox makes a leaping catch in the eighth inning agains the Baltimore Orioles at Fenway Park on April 12, 2019 in Boston, Massachusetts. (Photo by Kathryn Riley /Getty Images)
BOSTON, MA - APRIL 12: Jackie Bradley Jr. #19 of the Boston Red Sox makes a leaping catch in the eighth inning agains the Baltimore Orioles at Fenway Park on April 12, 2019 in Boston, Massachusetts. (Photo by Kathryn Riley /Getty Images) /

The curious case of the Red Sox outfield

Well my friends, right when we think baseball is about to come to 2020, it gets ripped right from our hands. In the span of a week we went from the players not negotiating, to the owners not negotiating, to a deal being done, and finally a deal nowhere close. For the Red Sox, this is just the start of their issues as they have a full plate without this debacle.

Remember that time the Red Sox traded a five-tool superstar that could be the face of the franchise for his entire career? Unfortunately, I think we all do. When Boston traded away Mookie Betts ahead of the 2020 season it was a massive blow on and off the field. As far as the on the field is concerned it created a bit of a conundrum in the outfield.

Not only is Mookie set to be a free agent in 2021 but so is Jackie Bradley Jr. and the newly signed Kevin Pillar. This essentially leaves just Andrew Benintendi and the recovering Alex Verdugo running the outfield. Last time I checked, you need three guys out there. If we check the crystal ball for the 2021 free agency class, it’s riddled with either more expensive or older players, not quite what Boston wants right now.

So how can Chaim Bloom combat the impending exodus of outfielders from Boston?

Where does the Red Sox outfield go from here?

I highly doubt Boston will re-sign Mookie in free agency. As much as I’d love to have him roaming right field again, his price tag may be out of the budget. On the other side of that coin with the gigantic financial hit the league is taking thanks to COVID, his price may go down and the chance may be there. I sure don’t like he’s going to be in the $350M neighborhood that he would’ve been had 2020 gone as planned.

Verdugo is dealing with some back issues but a few months ago he got some positive news from the doctors and was hitting regularly. He was set to be the heir apparent to Betts in right field but with JBJ also nearing the exit door, he could be back in his more natural centerfield role. Verdugo will have to get acquainted with that pesky triangle as well as the Green Monster but he can succeed.

Benny will be the general of the outfield for the next few seasons. He’s not set to hit free agency for some time and with his comrades being shuffled around, he’s the veteran voice out there. Benintendi also has the ability to cover centerfield and can push Verdugo back to right. I’m not a fan of that plan as Benny is easily on of the best left-fielders in the game right now and I’d hate to take him from his sweet spot. When all is said and done he may be one of the best to ever man the Green Monster.

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Then we have the duo of free agents in JBJ and Pillar. Both are in their early 30’s and each has seven seasons in the big leagues. Neither player lights the world in fire at the plate and both are known more for their defensive abilities. I love what Bradley has done in Boston but if I’m looking at this purely based on salary, I’m re-signing Pillar. JBJ was set to earn $11M in 2020 compared to Pillar’s $4.25M.

With the Red Sox becoming more financially conscious, I don’t know if Bloom would want to write Jackie another big check. Chaim could always go to his talent pool in the minors, especially with the MiLB season being canceled. There are some great options out there in C.J. Chatham and Jarren Duran, but neither are ready just yet. If this was 2021 going into 2022, then I’d make some calls to the farm system, but not yet.

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Chaim Bloom and the Red Sox need to act swiftly with this issue before it becomes something too big to conquer. The path of least resistance would be to offer a short-term deal to either Pillar or Jackie and keep them in Boston for the next few years. That’ll buy the Sox some time to continue developing Chatham and Duran for the future. With zero ideas of what 2020 is going to look like as we work out way through June, it’s hard to plot out the solutions to the problem.