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The Boston Red Sox have not yet identified their next top baseball operations executive after dismissing Chaim Bloom near the end of the season, yet they may have already identified their top offseason priority. According to Red Sox team president and CEO Sam Kennedy, the club intends to be aggressive this winter in signing their best young players to long-term extensions.

"I think it's really important. I think the best organizations really go out of their way to try and shore up the players that they feel that they have real strong conviction in," Kennedy said during an appearance on MassLive's Fenway Rundown podcast. "That effort has absolutely been there. In certain instances, we haven't yet done that. We were able to make a deal with Garrett Whitlock, for example, along those lines. And there's been conversations with other guys.

"We should be able to determine which players would qualify for longer-term extensions, whether it's Bello, whether it's Abreu, whether it's Duran or Casas. These are really important decisions that our baseball operations people have to make."

It should not register as a surprise that the Red Sox (or any team, for that matter) want to sign long-term deals with young players. MLB's pay structure is slanted in a way that gives players their lowest earning potential (and therefore the least leverage) early on in their careers. In other words, the first few seasons of a player's big-league stay is usually when teams can get the "best deal" for themselves and, in turn, the worst deal for the player.

What is notable here is that Kennedy explicitly named several players, including right-handed pitcher Brayan Bello, first baseman Tristan Casas, and outfielders Jarren Duran and Wilyer Abreu. Perhaps Kennedy was merely rattling off the first young players that came to mind, or perhaps that's an indication that those four players in particular will be extension candidates. 

PlayerAgeMLSCareer WAR



< 2 years




< 2 years




< 2 years




< 1 year


This is pure conjecture on our part, but it would also make some sense for the Red Sox to investigate long-term extensions with top prospects like shortstop Marcelo Mayer and outfielder Roman Anthony. Although neither has debuted in the majors, teams have grown more comfortable in recent years signing players to lengthy extensions before they've reached The Show. 

The Red Sox went 78-84 in 2023, finishing last in the American League East for a second consecutive year and the fifth time in the last 10 seasons.