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.
