Jordan Montgomery

The Red Sox have been continually connected to free agent 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 today 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, though 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 earned run average. 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 $211MM, which is $26MM below this year’s base threshold of $237MM. 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 $133MM. 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.

The Red Sox have been tied to Jordan Montgomery for the bulk of the offseason. Reporting last week indicated the Sox remained interested in the left-hander but continued to wait for his asking price to drop.

ESPN’s Buster Olney tweeted this morning that the Red Sox had “recently” conducted a Zoom meeting with Montgomery. Manager Alex Cora confirmed to the Boston beat the meeting took place but indicated it happened before the beginning of Spring Training.

“Buster is right,” Cora said (link via Christopher Smith and Sean McAdam of MassLive). “We zoomed with him. But we’ve been zooming with a lot of people throughout the offseason. I’m not going to get into specifics but yeah, it’s part of the process. It was a while ago, too. I was in South Beach for that one. I was in Miami.” Smith and McAdam point out that Cora was in Miami on the weekend of February 9-11 to watch the end of the Caribbean series and take part in a University of Miami alumni event.

Clearly, that conversation didn’t result in an immediate agreement. With Montgomery still on the market two and a half weeks later, the Sox remain a logical fit. They haven’t markedly upgraded their rotation throughout the winter. Boston took a flier on Lucas Giolito before shipping out Chris Sale for second baseman Vaughn Grissom.

They’re currently set to enter the season with a front four of Giolito, Brayan Bello, Nick Pivetta and Kutter Crawford. Righties Tanner Houck, Garrett Whitlock and Josh Winckowski would battle for the final spot. Installing Montgomery atop the group would allow Boston to keep the latter three arms in multi-inning relief roles to begin the year.

[Related: Where Does The Market Stand For Jordan Montgomery?]

The question is whether his asking price will fall to a level with which the Red Sox are comfortable. CEO Sam Kennedy sam last month the Sox anticipated opening the season with a lower payroll than they had in 2023. Roster Resource calculates their 2024 CBT number around $202MM. That’s nowhere near the $237MM base threshold and around $23MM shy of last year’s estimated mark. Signing Montgomery wouldn’t push the Sox into CBT territory, but it would likely push them close to their 2023 spending range.

One of the “Boras Four,” Cody Bellinger, came off the market over the weekend on a three-year deal. The $80MM guarantee was nowhere near what his camp had sought early in the offseason. A reported ask above $200MM never materialized, leaving Bellinger to settle for a modified pillow contract that could allow him to retest free agency via opt-outs in either of the next two offseasons.

That kind of contract might not be as appealing to Montgomery. He recently turned 31 and was ineligible for the qualifying offer this offseason thanks to the midseason trade sending him from St. Louis to Texas. If he took an opt-out laden deal, he could have to wrestle with draft compensation in a future offseason. Montgomery is coming off a third straight year in which he reached 30 starts. He tossed a personal-high 188 2/3 innings with a 3.20 ERA that was the best mark of his career. He added 31 innings of 2.90 ERA ball over six postseason outings to help the Rangers to the first title in franchise history.

The end of February is now less than a week away and Spring Training games have begun, yet plenty of significant free agents remain unsigned. As long as they linger on the open market, they will continue to be the subject of discussion. That’s particularly true of the “Boras Four,” which is formed by Blake Snell, Jordan Montgomery, Cody Bellinger and Matt Chapman, all of whom are represented by the Boras Corporation.

The Red Sox have been loosely tied to Montgomery throughout the offseason and that connection was addressed this morning by both Rod Bradford of WEEI and Sean McAdam of MassLive. Bradford reports that the club appears to prefer Montgomery to other available free agents but it is still waiting for the price to come down. McAdam frames it similarly, noting that the club has stayed in contact with Scott Boras “as a matter of course.” McAdam also suggests the Sox could fit Montgomery into their budget if his asking price drops, but he also points out that several other clubs would jump into the fray at that point. At any rate, it seems to be a moot point for now since McAdam relays that the asking price has not dropped.

The fit between the two sides is a sensible one in some ways. Montgomery’s wife is doing a residency at a Boston hospital and there would surely be some appeal to the convenience of working in the same city for much of the year. But beyond that, the club has been searching for starting pitching all winter and hasn’t really found it. They did sign Lucas Giolito but also traded away Chris Sale, leaving them roughly where they started. One might argue that Giolito is an upgrade on Sale but that substitution doesn’t address the overall depth.

The Red Sox have also been quieter than some other traditional big spenders. While clubs like the Yankees and Dodgers are well beyond the fourth and final luxury tax tier, the Sox aren’t even above the lowest threshold of $237MM. Boston’s competitive balance tax figure is at $202MM, per Roster Resource, which gives them plenty of room to theoretically make a big splash and still avoid the tax. Some other clubs like the Padres, Rangers, Mariners and Twins seem to be operating with diminished spending capacity this winter due to uncertainty in their TV revenue situations.

All that could perhaps put the Red Sox in a position to strike, but there are also reasons to suspect it won’t happen. The club’s president Sam Kennedy was recently present as Spring Training facilities and spoke to the media, with Christopher Smith of MassLive relaying some video. “We have set parameters for him,” Kennedy said in response to a question about whether chief baseball officer Craig Breslow has a hard budget. “He’s operating under those parameters.” He declined to elaborate with specifics.

All teams have budgets but there can sometimes be a point where opportunities push a club to alter their plans. Both the club and Boras appear to be holding their positions for now and time will tell whether one side blinks or if the staredown leads to Montgomery signing elsewhere.

It’s possible something will happen to get things moving, but the Sox might proceed into the season with their current rotation mix. Last month, Breslow said the rotation consists of Giolito, Brayan Bello, Kutter Crawford and Nick Pivetta. That would leave Garrett Whitlock, Tanner Houck and Josh Winckowski as options for the final spot.

Giolito has plenty of success in his career but his earned run average has finished just below 5.00 in each of the past two seasons. Bello and Crawford each have just over 200 major league innings under their belts. Pivetta’s 2023 finished strong but he was bumped to the bullpen for a time due to some shaky results. The latter three worked both as starters and relievers in their careers and are still trying to establish themselves as legitimate rotation options.

There’s plenty of uncertainty in that mix and an addition would make sense if the Sox are willing to add some money to the payroll. In addition to Snell and Montgomery, the free agent market still features Michael Lorenzen, Mike Clevinger, Rich Hill, Zack Greinke and others. In addition to the Sox, Montgomery has received reported interest from clubs like the Angels and Giants, with other clubs making logical sense. MLBTR predicted him for a six-year, $150MM deal coming into the winter but his continued stay in free agency suggests that he hasn’t had offers in that vicinity and the chances of him getting there will likely drop as time goes on.