World Series-winning pitcher seeking long-term deal that Red Sox are unwilling to give him

The Red Sox have been continually connected to free-agent pitcher Jordan Montgomery as he has remained unsigned throughout the offseason, but without a deal seeming close to fruition. Jon Heyman of the New York Post reports that the two sides have stayed in contact but that the lefty is looking for a seven-year deal that the club is unwilling to give.

There are arguments for and against the Red Sox making a huge splash to improve the rotation at this point. From the start of the offseason, upgrading the starting staff has been a priority but the club hasn’t done it. They traded away Chris Sale and then signed Lucas Giolito, which amounted to something close to a lateral move, depending how one feels about those two pitchers. But it was recently reported that Giolito has a partial tear of his UCL and a flexor strain. The next steps still aren’t known but season-ending surgery is a possibility.

If Giolito is out of commission, then the Sox are essentially going into the season with the same rotation as last year but without Sale. Nick Pivetta struggled enough last year to get bumped to the bullpen, but he did finish the year strong. Brayan Bello had a decent year and the club clearly believes in him, since they just signed him to an extension, but he seemed to run out of gas late in the year and the low strikeout rate is still a bit of a concern. Kutter Crawford, Tanner Houck and Garrett Whitlock are talented arms to fill out the rest of the staff but those three are still not fully established as starters, with none of that trio having hit 130 innings in a big league season. Cooper Criswell, Brandon Walter and Chris Murphy are on the 40-man as depth but no one in that group has 50 big league innings pitched yet.

Adding someone like Montgomery would be a clear upgrade, both this year and in the future. He has thrown 524 1/3 innings over the past three seasons with a 3.48 ERA. He tossed another 31 frames in last year’s postseason with a 2.90 ERA, forming a key part of the Rangers’ World Series championship club. Pivetta is slated for free agency after 2024, so the need for rotation help should be even greater a year from now.

But the flip side of the argument is that the Sox may want to wait to put another big contract on their books. They are considered by many observers to be the weakest club in the American League East. The club’s lack of activity this offseason suggests they may view things similarly. Perhaps they don’t want to commit a huge pile of money to Montgomery when they don’t have faith in their current squad.

When a club signs a player to a long-term deal, they generally expect to recoup the most value in the early years when the player is still relatively close to their prime, and clubs are also aware that the later years might be a bit more painful. If the Sox don’t think they have a path to contention right now, perhaps they don’t have much desire to get a deal done with the 31-year-old Montgomery.

Instead, they could use 2024 as a year to evaluate younger players like Ceddanne Rafaela, Wilyer Abreu, Vaughn Grissom, Kyle Teel, Nick Yorke, Marcelo Mayer, Roman Anthony and others. They could trade impending free agents like Pivetta, Kenley Jansen, Chris Martin and Tyler O’Neill this year to further stock up on young talent, then decide on the best time to make a big strike in the future. They could bolster the rotation in the short-term by signing someone like Michael Lorenzen or Jake Odorizzi.

RosterResource currently lists their competitive balance tax figure as $211M, which is $26M below this year’s base threshold of $237M. They could fit in a big deal for someone like Montgomery without going over the line but it would be fairly close. Next year’s CBT number, on the other hand, is only at $133M. That doesn’t include raises for arbitration-eligible players but the appetite for a giving out a big contract might be higher going forward than it is now.

For Montgomery, the fact that he is still unsigned as we approach the middle of March suggests that no club has met his asking price yet. It’s understandable that he is looking to maximize his guarantee here this winter, as he is coming off a great season and just helped the Rangers win the World Series.

This winter’s market has forced some other free agents to pivot to short-term deals, most notably Cody Bellinger and Matt Chapman. Those two, like Montgomery and Blake Snell, are all represented by the Boras Corporation. Boras clients have generally had a stronger willingness to wait out the market than players with other agencies. But Bellinger and Chapman didn’t find the long-term deals they were seeking and pivoted to shorter pacts with opt-outs that will allow them to return to free agency next winter or the one after that. Reporting has suggested Snell is willing to do the same.

Montgomery may be less inclined to do so, however, since he didn’t receive a qualifying offer at the start of this offseason. Players traded midseason are ineligible to receive a QO and Montgomery was flipped from the Cardinals to the Rangers prior to the deadline. That means he can currently be signed without the club forfeiting any draft picks or international bonus pool money. If he were to pivot to a short-term deal with opt-outs, he would be highly likely to receive a QO whenever he decided to return to the open market, which would put a damper on his earning power at that point. He would also obviously be older and therefore less likely to find a club willing to make a long-term commitment to him.

It’s theoretically possible that he could sign a short-term deal and then be traded at midseason again, though he wouldn’t be able to control that. Clubs are also fairly unwilling to acquire such contracts at the deadline, as they would be taking on the downside of being committed to the player for many years if they got hurt and decided not to trigger their opt-out.

With Montgomery seemingly sticking to his seven-year ask, it suggests he and his reps are perhaps aware that the he is a less viable fit for the pivot to a short-term pact than Bellinger, Chapman or Snell. But he hasn’t found the right deal yet and time will tell if he does end up getting it.