The Red Sox have consistently been linked to free-agent pitcher Jordan Montgomery, who has remained unsigned throughout the offseason. However, there hasn’t been significant progress toward a deal. According to Jon Heyman of the New York Post, discussions between the two parties have continued, but Montgomery is seeking a seven-year contract, which the club is unwilling to offer.
There are pros and cons to the idea of the Red Sox making a significant move to bolster their rotation at this stage. Improving the starting pitching has been a priority since the offseason began, but the team has yet to make a substantial move. They traded Chris Sale and brought in Lucas Giolito, which some might see as a lateral move depending on their assessment of the two pitchers. However, recent reports indicate that Giolito has a partial tear in his UCL and a flexor strain. The next course of action is uncertain, but season-ending surgery is a possibility.
If Giolito is sidelined, the Red Sox will essentially be entering the season with a rotation similar to last year’s, minus Sale. While Nick Pivetta struggled enough last season to be relegated to the bullpen initially, he finished the year on a high note. Brayan Bello showed promise but appeared to tire towards the end of the season, and his low strikeout rate remains a concern. Although the club extended him, indicating their belief in him, his durability and strikeout ability are still in question.
Kutter Crawford, Tanner Houck, and Garrett Whitlock are talented pitchers to round out the rotation, but none of them have yet accumulated over 130 innings in a major league season, making their reliability as starters uncertain. Cooper Criswell, Brandon Walter, and Chris Murphy provide depth on the 40-man roster, but none of them have significant experience at the major league level, with none having pitched more than 50 innings.
Acquiring someone like Montgomery would represent a clear upgrade, both for the upcoming season and beyond. Over the past three seasons, Montgomery has pitched 524 1/3 innings with a 3.48 ERA. In last year’s postseason, he contributed 31 innings with a 2.90 ERA, playing a crucial role in the Rangers’ World Series victory. With Pivetta set for free agency after 2024, the need for rotation reinforcement could become even more pressing next year.
On the contrary, the Red Sox might be hesitant to add another significant contract to their payroll. Many observers regard them as the weakest team in the American League East, a sentiment reflected in their limited activity during the offseason. This lack of action suggests they may share similar doubts about their current roster. It’s possible they are reluctant to commit a substantial sum to Montgomery without confidence in their current squad.
When clubs sign players to long-term deals, they typically expect to derive the most value in the early years, when the player is nearer to their prime, while acknowledging that the later years could be more challenging. If the Red Sox believe they are not in a position to contend at present, they may not be inclined to strike a deal with the 31-year-old Montgomery.
Instead, they might view 2024 as an opportunity to assess younger players like Ceddanne Rafaela, Wilyer Abreu, Vaughn Grissom, Kyle Teel, Nick Yorke, Marcelo Mayer, Roman Anthony, and others. They could also opt to trade impending free agents such as Pivetta, Kenley Jansen, Chris Martin, and Tyler O’Neill to accumulate more young talent, and then determine the optimal timing for a significant move in the future. In the short term, they could strengthen the rotation by signing players like Michael Lorenzen or Jake Odorizzi.
RosterResource currently indicates their competitive balance tax figure at $211 million, which is $26 million below this year’s base threshold of $237 million. They could potentially accommodate a significant deal for someone like Montgomery without surpassing the limit, although it would be a close call. However, next year’s competitive balance tax number stands at only $133 million. While this doesn’t factor in potential raises for arbitration-eligible players, there may be a greater willingness to entertain a major contract in the future compared to the current situation.
The fact that Montgomery remains unsigned as we approach mid-March suggests that no team has yet met his desired price. Given his strong performance last season and his contribution to the Rangers’ World Series victory, it’s understandable that he seeks to maximize his earnings this offseason.
This offseason’s market dynamics have led some other free agents to adjust their strategies towards short-term deals, notably Cody Bellinger and Matt Chapman. These players, along with Montgomery and Blake Snell, are all represented by the Boras Corporation. Historically, Boras clients have been more inclined to wait out the market than those represented by other agencies. However, Bellinger and Chapman didn’t secure the long-term contracts they sought and opted for shorter agreements with opt-outs, allowing them to revisit free agency in the near future. Reports indicate that Snell may be open to a similar approach.
Montgomery might be less inclined to pursue a short-term deal with opt-outs, primarily because he didn’t receive a qualifying offer at the beginning of the offseason. Players traded midseason are ineligible for a qualifying offer, and since Montgomery was traded from the Cardinals to the Rangers before the deadline, he falls into this category. Consequently, he can currently sign without the club forfeiting any draft picks or international bonus pool money.
Opting for a short-term deal with opt-outs would likely lead to Montgomery receiving a qualifying offer when he re-enters the market, which could limit his earning potential at that point. Additionally, he would be older by then, making it less probable for a team to offer him a long-term commitment.
While there’s a theoretical possibility that Montgomery could sign a short-term deal and be traded again midseason, he wouldn’t have control over this scenario. However, teams are typically reluctant to acquire such contracts at the deadline due to the potential downside of being committed to the player for several years if they get injured and choose not to exercise their opt-out clause.
Montgomery’s insistence on his seven-year request suggests that he and his representatives may recognize that he is less suited for a shift to a short-term deal compared to players like Bellinger, Chapman, or Snell. However, he has yet to secure the right deal, and only time will tell if he ultimately finds it.