The Red Sox have been continually connected to free agent as he has remained unsigned throughout the offseason, but without a deal seeming close to fruition. 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 hasnt done it. They traded away and then signed , which amounted to something close to a lateral move, depending how one feels about those two pitchers. But it was that Giolito has a partial tear of his UCL and a flexor strain. The next steps still arent known but season-ending surgery is a po sibility. If Giolito is out of commi sion, then the Sox are e sentially going into the season with the same rotation as last year but without Sale. struggled enough last year to get bumped to the bullpen, though he did finish the year strong. had a decent year and the club clearly believes in him, since they just signed him to , but he seemed to run out of gas late in the year and the low strikeout rate is still a bit of a concern. , and 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. , and 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 Matthew Poitras Jersey 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 to sed another 31 frames in last years 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 clubs lack of activity this offseason suggests they may view things similarly. Perhaps they dont want to commit a huge pile of money to Montgomery when they dont 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 dont think they have a path to contention right now, perhaps they dont 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 , , , , , , and others. They could trade impending free agents like Pivetta, , and 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 or . currently lists their competitive balance tax figure as $211MM, which is $26MM below this years 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 years CBT number, on the other hand, is only at $133MM. That doesnt 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. Its 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 winters market has forced some other free agents to pivot to short-term deals, most notably and . Those two, like Montgomery and , are all represented by the Boras Corporation. Boras clients have generally had a stronger willingne s to wait out the market than players with other agencies. But Bellinger and Chapman didnt 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 le s inclined to do so, however, since he didnt 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 le s likely to find a club willing to make a long-term commitment to him. Its theoretically po sible that he could sign a short-term deal and then be traded at midseason again, though he wouldnt 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 le s viable fit for the pivot to a short-term pact than Bellinger, Chapman or Snell. But he hasnt found the right deal yet and time will tell if he does end up getting it. Billy Sweezey Jersey