Starting pitching, or lack thereof, has been the name of the game the last few seasons for the Boston Red Sox. The lack of starting depth cost them in 2023, as a free-fall at the end of August and all of September led to their second straight last-place finish in the American League East.

The offseason brought largely crickets in the starting pitching department — the Sox signed only Cooper Criswell, who has just two games of big-league starting experience, and Lucas Giolito. Now, Giolito is out long-term with an elbow injury that requires surgery, leaving the Red Sox in an even more precarious position than ever before.

There is a set of parameters for this winter’s spending which may not allow Craig Breslow to go over the luxury tax threshold, or seemingly near it. With the first luxury tax threshold at $237 million for 2024 and the Red Sox payroll hovering around $161 million, they still have lots of wiggle room.

There is still time for upgrades to the starting rotation to make a dire situation a little less so. The Red Sox could sign any of these free-agent pitchers and remain under the first threshold.

Jordan Montgomery

It’s well into spring training and Jordan Montgomery has not signed with Boston. It’s the most obvious match of player and team all winter and it hasn’t happened. Montgomery is everything the Red Sox need, both before the Giolito injury and after.

The most important thing is that Montgomery has been a good pitcher the last few years and was a playoff warrior in 2023, so he’d be the top-of-the-rotation arm the Red Sox sorely need right now. He’s also able to throw a lot of innings, surpassing 155 innings pitched in each of the last three seasons. He is healthy more often than not, which is also something the Red Sox haven’t had a lot of luck with recently.

Montgomery is a lefty, which is another big need for the Red Sox in the rotation. Brayan Bello, Nick Pivetta, Kutter Crawford, Garrett Whitlock, Tanner Houck, and Criswell are all righties, with no clear lefty starter option in sight.

There aren’t a lot of teams pursuing Montgomery right now, it’s basically a staring contest between him and the Red Sox. Boston needed to sign Montgomery before Giolito went down, and it’s a move it still needs to make now.