June 23, 2024

The Red Sox have maintained contact with free-agent pitcher Jordan Montgomery throughout the offseason, but a deal has yet to materialize. According to Jon Heyman of the New York Post, Montgomery is seeking a seven-year contract, a term that the club is unwilling to meet.

The Red Sox have been prioritizing upgrades to their starting rotation, but significant moves have yet to materialize. They traded away Chris Sale and signed Lucas Giolito, which some view as a lateral move. However, Giolito’s recent injury concerns have added uncertainty to the rotation.

If Giolito is sidelined, the Red Sox could enter the season with a rotation similar to last year’s, minus Sale. While Nick Pivetta struggled at times, he finished the season on a positive note. Brayan Bello, despite a decent year, showed signs of fatigue late in the season, and his low strikeout rate remains a concern. Kutter Crawford, Tanner Houck, and Garrett Whitlock offer talent but lack extensive experience as starters. Cooper Criswell, Brandon Walter, and Chris Murphy provide depth, but none have significant big league innings.

Acquiring someone like Montgomery would be a significant upgrade, both in the short term and long term. Over the past three seasons, he has amassed 524 1/3 innings with a 3.48 ERA. His postseason performance last year, with a 2.90 ERA, was crucial in the Rangers’ World Series victory. With Pivetta set for free agency after 2024, the need for rotation help may become even more pressing in the future.

The flip side of the argument is that the Red Sox may hesitate to add another significant contract to their payroll. Many observers consider them the weakest team in the American League East, and their lack of offseason activity may indicate a similar view from the organization. Committing a large sum to Montgomery could be seen as risky if they lack confidence in their current roster.

When teams sign players to long-term deals, they typically expect the most value in the early years, when the player is closer to their prime. The later years of the contract may present challenges, especially if the player’s performance declines. If the Red Sox don’t see a clear path to contention, they may be reluctant to sign the 31-year-old Montgomery to a long-term deal.

Alternatively, the Red Sox could use 2024 as a year to evaluate young talent like Ceddanne Rafaela, Wilyer Abreu, Vaughn Grissom, and others. They could trade impending free agents to acquire more young talent and wait for a better opportunity to make a significant move in the future. Short-term solutions like signing Michael Lorenzen or Jake Odorizzi could help bolster the rotation in the interim.

While the Red Sox could afford a big contract for Montgomery without exceeding the competitive balance tax threshold this year, their future CBT number is significantly lower. This could influence their decision-making going forward, especially considering potential raises for arbitration-eligible players.

Montgomery’s current unsigned status suggests that no team has met his asking price yet. He may be seeking a long-term deal to maximize his earnings after a successful season with the Rangers. Other free agents represented by the Boras Corporation have opted for short-term deals with opt-outs, but Montgomery’s lack of a qualifying offer makes this strategy less appealing.

Signing a short-term deal with opt-outs could lead to a qualifying offer in the future, limiting Montgomery’s earning potential. Additionally, he may be less likely to find a team willing to make a long-term commitment as he gets older. While a trade midseason is possible, it would come with risks for both Montgomery and any acquiring team.

Overall, Montgomery’s insistence on a seven-year deal suggests that he and his representatives believe he is less suited for a short-term pivot compared to other players. However, his future in free agency remains uncertain as he seeks the right opportunity.

Red Sox unwilling to give this pitcher long-term deal

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