If the Boston Red Sox chose to let go of superstar outfielder Mookie Betts at a time when he was arguably the best player in Major League Baseball besides Los Angeles Angels outfielder Mike Trout, why would they be motivated to sign third baseman Rafael Devers entering a contract year?
The situations surrounding the star players are quite different, and the Red Sox are better suited to back up the brinks truck for Devers in the present scenario than Betts ahead of the 2020 season.
Red Sox chief baseball officer Chaim Bloom explained at length why he'd be more likely to work out a deal with Devers now than Betts years ago, but here is the summarization:
"We are in a different position as an organization," Bloom told Rob Bradford on WEEI's "Bradfo Show" on Monday. "I think the young talent in the organization is in a much better spot and we are not committed in the same way financially to as many players as we were (in 2020)."
It's not about the players -- both are fantastic -- it's about the circumstances surrounding the timing of the deals.
Here are two reasons why Devers makes a lot more sense to sign than Betts:
The Red Sox have more financial flexibility to sign a substantial long-term deal Boston always will have the money to pay up for an individual contract at virtually every price; that was not the issue and never will be. The problem Bloom faced with Betts was the lack of payroll flexibility surrounding the larger contracts.
Former Red Sox president of baseball operations Dave Dombrowski chose to sling out sizeable deals without any regard for the future in a failed attempt to win another championship in 2019. The way Dombrowski operated placed Bloom in a terrible circumstance, with notable contracts for oft-injured left-handed pitcher Chris Sale, fellow southpaw David Price (who was shipped to the Los Angeles Dodgers in the Betts trade but still was owed money from Boston), and a myriad of overpriced mid-level deals.
The team also was still paying injured second baseman Dustin Pedroia and the absolutely useless third baseman Pablo Sandoval.
Bloom managed to get most of the "bad" deals off of the books and now just has Sale's deal as the only notable contract that still hurts. He'll have the ability to both extend Devers and build around him. Had he signed Betts, he would not have been able to put the necessary pieces around him to win a championship.
The farm system is in a much better place than it was years ago When Bloom took the reigns of the Red Sox's front office, the farm system was ranked No. 25 by MLB Pipeline due to Dombrowski's aforementioned lack of regard for the future. In just three seasons (including a pandemic that severely altered 2020) Bloom has brought the system up to No. 11.
If the majority of the roster is built on budding talent on rookie deals, it's easier to go out and sign a star player. The Red Sox were in a position where free agency was the only place where they could improve their team. It's hard to sign big deals when the team has to infuse veteran talent (also via free agency) to put the bulk of the roster together as well.
The budding farm system can help Bloom not only with depth the roster previously did not have but to acquire impact players. Top prospects can be used as trade chips to improve the team without having to pay marquee-free agents.
Say what you want about Bloom, but extending Betts in 2020 with a bad farm system and a lack of quality talent at the major league level would have been a terrible venture. Don't believe me? Just take a look at the Angels, who boast arguably the top two players in the game and still are absolutely horrendous.
More Red Sox: Chaim Bloom Explains Why He'd Sign Rafael Devers Over Mookie Betts
Scott Neville covers the Boston Red Sox for Sports Illustrated's new page "Inside The Red Sox." He got his start covering the team for NESN after graduating from Merrimack College in 2021.