The Boston Red Sox are one of the most renowned franchises in recent MLB history. Over the past 15 years, they have won three World Series championships, but this season has greatly disappointed the organization. Signing Trevor Story in the offseason seemed to be a band-aid solution as the front office has not prioritized the extensions of Xander Bogaerts and Rafael Devers.

Bogaerts and Devers have been loyal to the franchise since the start of their careers, but Boston has not seriously negotiated with both parties. Bogaerts was offered a one-year, $30 million contract extension, which was a shocking offer from the Red Sox. This is Xander Bogaerts, the franchise cornerstone of the Red Sox, and he cannot get a gigantic extension from a wealthy organization?

That is a significant cause for concern, and one of several reasons why it seems unlikely Bogaerts will re-sign with Boston.

3 reasons why Xander Bogaerts will not re-sign with the Red Sox in free agency

3. His agent, Scott Boras

Power agent Scott Boras is notorious for encouraging his clients to test the market in hopes of securing the biggest possible bag from the most alluring possible free agent destination. Boras is a terrific negotiator who normally ends up getting what he desires. For instance, declining a $440 million offer to Juan Soto from the Washington Nationals was a move that required a ton of courage. Boras knew Soto deserved more, and that another organization would be willing to pay him when he enters free agency in 2024.

Tteams like the New York Yankees, Philadelphia Phillies and Houston Astros could target a shortstop in free agency during the offseason. These franchises are known to spend in free agency, making them attractive prospective suitors to Bogaerts, a player who deserves a big-money payday and the organizational clout that comes with it.

Boston hasn't treated a player of Bogaerts' caliber fairly in extension talks, and Boras is bound to react accordingly by directing the four-time All-Star elsewhere in free agency.

2. Subpar defense for Bogaerts

Some shortstops who are paid an enormous amount could excel at that position for the rest of their careers. Francisco Lindor and Carlos Correa thrive as hitters and fielders, but Xander Bogaerts has been inconsistent as a fielder for most of his career. He has improved a ton from the beginning of his MLB tenure, but he is from a Gold Glove-worthy shortstop.

Legendary shortstops like Derek Jeter have excelled defensively, a vital position in the infield. Bogaerts does not commit an especially large number of miscues or errors, but his defensive runs saved are a problem regardless. Bogaerts is also not getting any younger, so at 29 years old, he may only be able to provide a couple more years of adequate defense. Story could always slide over to shortstop for the Red Sox, but they would only be at their best going forward if Bogaerts remains a capable fielder.

1. Trea Turner and Dansby Swanson are FA in 2023 

Age is a critical factor affecting player performance at any position in baseball, but especially shortstop. With Story seemingly entrenched as the Red Sox's highest-paid player, the franchise could decide to go after a pitcher, first baseman or outfielder this offseason. Furthermore, Bogaerts is in an unlucky position because he is a free agent the same same year as superstar shortstops Trea Turner and Dansby Swanson, who Boston may prefer.

Turner and Swanson possess a more well-rounded arsenal than Bogaerts, ensuring their partnership with Story could be spectacular. As a Boras client, Bogaerts may only be willing to accept a long-term deal from Boston that allows him to finish his career where it started. That type of offer may not be beneficial for the franchise, especially over the latter half of its duration. Thus, choosing a shorter-term deal with Turner or Swanson could be a more plausible outcome for Boston.