Any one of these five players would be affordable for Boston to sign.
For the Boston Red Sox, the previous several seasons have been all about starting pitching, or the lack of it. Their lack of starting depth proved costly in 2023, as they finished last in the American League East for the second time in a row due to a free slide at the end of August and the first part of September.
In terms of starting pitching, the offseason mainly produced nothing; the Sox only signed Lucas Giolito and Cooper Criswell, who has only started two games in the major leagues. With Giolito now sidelined for an extended period of time due to an elbow injury requiring surgery, the Red Sox are in much greater danger than they were before.
Craig Breslow might not be able to spend more than, or even close to, the luxury tax level under a set of restrictions for this winter. The Red Sox have plenty of leeway, with the initial luxury tax level set at $237 million for 2024 and their payroll now hovering around $161 million.
Upgrades to the starting lineup might still make a catastrophic scenario a little less severe. It is possible for the Red Sox to sign any of these free-agent pitchers and still fall below the first round cutoff.
The Red Sox could sign five pitchers while still being subject to the luxury tax.
Jordan Montgomery
Jordan Montgomery is far into spring training and still hasn’t signed a contract with Boston. It’s the most evident player-team match of the winter, and it hasn’t taken place. The Red Sox needed Montgomery before Giolito got hurt, and they still do.
The most crucial factor is that Montgomery would be the top-of-the-rotation arm the Red Sox really need right now. He has been a solid starter in recent years and was a postseason warrior in 2023. In each of the last three seasons, he has surpassed 155 innings pitched, demonstrating his ability to toss a lot of innings. He is typically healthy, which is another area in which the Red Sox have struggled recently.
The Red Sox also desperately need Montgomery to be a lefty in their rotation. There isn’t a single obvious lefty starter option in sight, with Brayan Bello, Nick Pivetta, Kutter Crawford, Garrett Whitlock, Tanner Houck, and Criswell being righties.
Right now, Montgomery and the Red Sox are essentially in a staring contest with very few teams vying for his services. Boston still needs to sign Montgomery, even though it should have done so before Giolito was hurt.
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