Red Sox Facing ‘Last Chance’ to Add Projected $110 Million Ace

Getty Red Sox manager Alex Cora has an inexperienced pitching rotation lined up in 2024.

If the Red Sox are going to make one last major move to bolster their starting rotation and bring in a pitcher who at least resembles an ace, well, they’re running out of time. It could very well be that there are no more chances left at signing last year’s postseason hero, lefty Jordan Montgomery, who is the last major piece remaining in what was a difficult offseason for big-name free agents.

It’s clear that, with Opening Day nearly upon us, Montgomery won’t be the No. 1 starter out of the gate for any team. His strategy now appears to be to wait for a team that suffers an injury in the rotation and is desperate enough to overpay him.

The Red Sox have had that injury, with expected ace Lucas Giolito out for the season with elbow surgery. If Montgomery is the answer, The Athletic’s Jen McCaffrey pointed out it’s got to happen now, in an article titled, “Jordan Montgomery remains on the market. It’s the Red Sox’s last chance to sign him.”

Wrote McCaffrey: “By some logic, if the Red Sox haven’t signed Montgomery by now, they probably aren’t going to. On the other hand, the Red Sox could add $25 million in payroll and still not hit the luxury tax threshold this season. But even if Montgomery has backed off his pursuit for a seven-year deal, like he was still seeking as of two weeks ago, the Red Sox are not the only team in need of pitching.”

Jordan Montgomery Banking on Pitching Injuries?

Indeed, the Yankees, Mets and Cubs have been among the teams suffering pitching injuries and possibly in the Montgomery mix. If the Red Sox are hoping that Montgomery’s price drops, they’ll need to remember that his price will drop for other teams, too. And those teams will offer him a better chance to return to the postseason than he’ll get in Boston.

Montgomery has been holding out for a long-term deal, as did several fellow clients of superagent Scott Boras. But those others—Cubs slugger Cody Bellinger, Giants third baseman Matt Chapman, Giants pitcher Blake Snell—all settled on short-term deals with opt-outs that allow them to hit free agency again. That hasn’t happened with Montgomery.

Spotrac has Montgomery’s value at $18.4 million per year, projecting a contract worth $110 million for six years. Alas, no such contract has been forthcoming as Spring Training has gone on.

Montgomery is 31 but has a career record of 38-34 with a 3.68 ERA. He struggled early in his career in New York but has been solid for two years since, going 19-17 with a 3.34 ERA in 64 starts for three teams. He was 3-1 in the Rangers’ playoff run to the championship last fall, with a 2.90 ERA.

Red Sox Rotation Lacks Experience

It’s hardly a Cy Young resume, but on a Red Sox team that currently is leading off with Brayan Bello as its ace and Nick Pivetta as the No. 2, Montgomery would be the top hurler on the staff right away. Bello is 24 and has 39 career starts under his belt. Pivetta went 10-9 last year in 38 appearances split between the rotation and the bullpen.

Kutter Crawford is the clear No. 3 and manager Alex Cora has Garrett Whitlock and Tanner Houck in the 4-5 slots. Newly signed Chase Anderson, a career starter, will likely work his way into the first five at some point, too, perhaps early in the year.

The Red Sox also have 27-year-old Cooper Criswell, who looked good in spring training, with a 2.95 ERA and 17 strikeouts against just three walks, in 18.1 innings. He will start at the season in Worcester.