
The Boston Red Sox have been gaining momentum recently, boasting a 48-40 record and securing the third American League Wild Card spot. While their recent success has shifted focus away from their lackluster offseason, there were high expectations for Red Sox chief baseball officer Craig Breslow to make significant moves, which ultimately fell short.

One notable target was left-handed pitcher Jordan Montgomery, who was heavily linked to Boston throughout the winter. However, despite being offered a multi-year contract by the Red Sox, Montgomery opted not to join the team, preferring to hold out for a return to the Texas Rangers, according to Jon Heyman of the New York Post.
Montgomery had an impressive 2023 season, posting a 3.20 ERA with a 166-to-48 strikeout-to-walk ratio, a .247 batting average against, and a 1.19 WHIP in 188 2/3 innings between the St. Louis Cardinals and the Rangers. However, since signing a one-year, $25 million contract with the Arizona Diamondbacks, including a vesting option for 2025, he has struggled with a 6.44 ERA and a 1.68 WHIP.
While Montgomery’s decision to avoid Boston may seem like a blessing in disguise given his current performance, it highlights a broader issue. Some marquee players are reluctant to join the Red Sox due to a perceived lack of commitment from ownership. Despite the allure of playing in a major market like Boston and calling Fenway Park home, principal owner John Henry has inadvertently turned it into a disadvantage in free agency.
For Montgomery, keeping his options open in the future would be wise, as his status as a highly coveted frontline starter has diminished.