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A hero of the Texas Rangers’ 2023 World Series win, Jordan Montgomery has been seeing his free agency linger far longer than expected this season. For a pitcher with his postseason experience and reliable track record, he should have normally been snapped up quickly. After initial favorites Texas seemed to be cool on the idea of a reunion, speculation ramped up surrounding a potential move to the East Coast. Could the New York Yankees’ archenemy, the Boston Red Sox, with their well-known need for a reliable starter, be the left-hander’s final destination?

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The rumors are swirling, and the longer Montgomery remains on the market, the more likely Boston seems to be his landing spot. But is this a sure thing? Could his former team make a late play? Or, might another contender emerge from the shadows?

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Red Sox: Why are they a compelling fit for Jordan Montgomery?

The Red Sox have a glaring need for stability in their starting rotation, and Montgomery fits the bill perfectly. They are aware of this issue themselves, as proven by their persevering pursuit after the ace. As insider Bob Nightengale pointed out recently in a USA Today report, “The Red Sox have kept in constant contact with Montgomery.”

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“He is a perfect fit for them,” another market report notes, though cautioned that Boston’s ownership needs to be willing to spend a fortune to secure him, considering his $170 million+ asking price. However, Jordan Montgomery’s track record, including his crucial postseason role with the Rangers, makes him a clear upgrade for Boston. Despite a less impressive offseason overall, hints of promise are emerging from the Red Sox Spring Training camp.

This potential, coupled with Montgomery’s addition, could transform the team into a contender. BoSox Injection draws a clear picture of the impact he would bring to the team mired by misfortune: “Somehow, the 2021 Red Sox made it just two games away from World Series contention. The 2023 squad was just a few games from a winning record.” A pitcher like him could be the missing piece. But they are not the only team with depth needs.

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Lingering Link vs. New Suitors

Throughout Monty’s extended free agency, a consistent rumor has linked him to Boston. Several reports suggest these rumors have substance, stating that “MLB team executives widely believe… Texas Rangers’ postseason hero Jordan Montgomery will wind up with the Boston Red Sox.” 

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Read More: Red Sox Ideal Fit for Jordan Montgomery, but Patience Could Spoil Plans

However, the door may not be closed on Texas, just yet. Nightingale himself believes that “The Rangers are keeping tabs if owner Ray Davis suddenly changes his mind.” Adding further complexity, the San Francisco Giants have emerged as a potential competitor for Montgomery’s services. With injuries in their rotation, the Giants have an immediate need that the left-hander could fill.

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Time is of the essence for all teams involved. Opening Day is quickly approaching, and Jordan Montgomery will need ample time to ramp up for the season. While Boston remains the apparent frontrunner, both the player and the team seem ready for this free-agency saga to end. Could an unexpected late surge from San Francisco change the narrative, or is Montgomery destined to don the iconic Red Sox uniform?

Read More: MLB Free Agency: 4 Top Contenders Left For Star Pitchers Blake Snell and Jordan Montgomery

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Written by

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Shrabana Sengupta

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Shrabana Sengupta is the Desk Editor at EssentiallySports with over a decade of experience in journalism and content management. She started as an MLB writer, covering key events like the 2023 World Series and Shohei Ohtani’s record-breaking contract with the LA Dodgers. After transitioning to an editorial role, she covered major events, including the 2024 Paris Olympics, 2025 Stanley Cup Playoffs, and 2025 Kentucky Derby over the past two years alongside other major sports. Specializing in tennis, she has now covered top tournaments such as the French Open, Wimbledon, and the US Open live in 2025. Renowned for her editorial insight, Shrabana consistently produces content that has earned recognition from officials across multiple sports leagues.

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Sampurna Pal

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