What Red Sox Learned From Mookie Betts Fiasco; How It Impacts Rafael Devers Talks

The Red Sox certainly sound like they learned a lot from their negotiations with the six-time All-Star

The Boston Red Sox have plenty of decisions to make this off-season. 

After a rough 2022 season that saw the Red Sox finish in last place in the American League East at 78-84, Boston has plenty of holes to fill. The most pressing matter for Boston certainly is the future of Xander Bogaerts. The four-time All-Star is a free agent and there is a real possibility that he may not be back in Boston in 2023, although there still is plenty of hope. 

On top of Bogaerts' future, the team will reportedly be extremely active in the free agent market outside of their star shortstop -- even potentially consider marquee free agents Aaron Judge and Justin Verlander -- but they also need to think the future of the team past 2023. 

Star third baseman Rafael Devers is up for an extension and will be commanding a massive deal himself. Boston has been in this position before with one of their young homegrown stars up for a massive extension but hasn't been to get the job done. Bogaerts comes to mind as the team actively is negotiating with the shortstop after failing to come to terms on an extension before the 2022 season kicked off. 

Another example of the team's failure to negotiate with a young homegrown star certainly is Mookie Betts. The 2018 American League Most Valuable Player was drafted by the Red Sox, worked his way up through the farm system, and spent the first six years of his MLB career in Boston before being dealt to the Los Angeles Dodgers ahead of the 2020 season in a package that brought Alex Verdugo to the Red Sox. 

Betts and the team -- similar to Bogaerts -- failed to come to terms on an extension before his final full season with the team and then never were able to come to an agreement before the team deal with the six-time All-Star. While Bogaerts may still re-sign with Boston, the Red Sox still have time to come to terms on a deal with Devers as well and it sure sounds like the team learned a lot from their negotiations with Betts.

“I think engaging with your players earlier — early and often — about arrangements that are mutually beneficial is something that well-run teams do and are doing," Kennedy said to the Boston Globe's Michael Silverman. "We just did that with Garrett Whitlock. We’ve had extensions for younger players in the past, and that’s certainly a lesson learned.

“We have not always been able to sign our own homegrown players long-term, I fully acknowledge that and when that doesn’t happen, it’s disappointing for the fans, and it’s disappointing for us on a personal level. But we get paid to make very, very difficult decisions, and we’ll see how those decisions work out.”

Boston certainly sounds like it is in a different place now than it was when the team was negotiating with Betts. The Red Sox reportedly will be one of the biggest spenders this offseason and even has sent an updated offer to Devers since the 2022 season came to an end. 

While no deal has been signed yet, it's certainly a welcomed sight that there seems to be progress. 

More MLB: Red Sox Made 'Several Offers' In Free Agency, Expect To Break News Soon