Why are the Red Sox still playing the waiting game with Jordan Montgomery?

With the first full week of Grapefruit League games underway, this is typically when roster battles are discussed and bullpen decisions are debated. Instead, one of the biggest question marks surrounding the Boston Red Sox is a player not even on the roster: free-agent left-hander Jordan Montgomery.

ESPN’s Buster Olney reported over the weekend that the Red Sox recently had a Zoom call with Montgomery and his agent, Scott Boras. Another Boras client, Cody Bellinger, signed with the Chicago Cubs on Sunday for a three-year, $80 million deal, widely considered to be below market value. Based on these two pieces of news, it would be fair to assume that Montgomery’s free agency decision should be concluding soon.

On Monday, Red Sox manager Alex Cora didn’t avoid the Montgomery questions.

“Buster is right,” Cora told reporters. “We zoomed with him. But we’ve been zooming with a lot of people throughout the offseason. I’m not going to get into specifics but yeah, it’s part of the process. It was a while ago, too. I was in South Beach for that one. I was in Miami.”

Cora was referencing the Caribbean Series in Miami from Feb. 9-11 that he’d attended before spring training. Did a somewhat recent Zoom with Montgomery mean anything? Is Bellinger’s deal a harbinger for a Montgomery deal the Red Sox might be more willing to sign? More importantly, why are we still debating this when there’s a clear need in the Red Sox’s rotation and a clear fit with Montgomery available?

Last week, when asked about the Red Sox’s offseason additions or lack thereof, Rafael Devers said what many in the clubhouse and those following the team were thinking, “everybody knows what we need.”

The Red Sox haven’t looked half bad this spring. Yes, it’s early, but camp has had an added intensity and focus, so perhaps that’s why it feels even more enticing to invest in Montgomery. The lone offseason addition to the rotation in Lucas Giolito has looked good in the early going, while it’s clear Brayan Bello, Garrett Whitlock, Tanner Houck and Kutter Crawford have taken steps forward. If only there was that one extra piece to push the Red Sox into a more likely spot for wild-card contention.

Make no mistake, Montgomery is not the sole elixir for this team. They still need several players to perform at the top of their potential from Giolito to Bello to Devers, Trevor Story and Triston Casas. But, as we’ve written here several times over the last few months, adding a starter like Montgomery to the mix can only help.

Last season, Montgomery posted a 3.20 ERA over 32 starts for the St. Louis Cardinals and Texas Rangers before putting up a 2.90 ERA in six playoff appearances for Texas, helping the Rangers win a World Series. He’s durable, having thrown 157 innings or more each of the last three seasons; has pitched in the American League East, coming up with the Yankees; and his wife is currently a dermatology resident at a Boston area hospital.

The Red Sox have such an obvious opportunity in front of them and have, up to now, still not made this work.

Chief baseball officer Craig Breslow has mentioned throughout the winter his goal of not jeopardizing the future for the present, but it’s not clear how a Montgomery deal would jeopardize the future. If the worry is about payroll, the only major contracts going forward are Devers, Story and Masataka Yoshida at the moment. A young, emerging core of prospects like Marcelo Mayer, Kyle Teel and Roman Anthony would inherently keep payroll down. Perhaps the Red Sox are planning on doling out several long-term extensions to that young core, in addition to Casas and Bello, but that seems unlikely to be done in quick succession.

At the moment, the Red Sox payroll sits around $205 million, well below the $237 million luxury tax threshold and well below last year’s team payroll of $225.7 million. There’s room to add Montgomery and still be below both of those marks, if that’s the goal.

On Sunday, Breslow joined the WEEI radio broadcast of the game and was asked if the Bellinger deal would open the market a bit for the rest of Boras’ clients to sign.

“I’m not sure we’re seeing the implications of Bellinger’s signing yet,” Breslow said on the broadcast. “I think a lot has been made of the constraints or parameters we are or aren’t working under. We’ll obviously continue to look at every opportunity that is out there to improve the team, while ensuring that we prioritize the long-term outlook alongside the shorter-term outlook. I don’t know, is the short answer, but it would be irresponsible not to find out (if the market is changing).”

Breslow later mentioned trading players this winter on “expiring contracts,” alluding to Chris Sale and Alex Verdugo, as a way to impact the club this season and in the future.

Meanwhile, the longer the wait for Montgomery, the more risk there is he won’t have a proper build-up this spring. He’s surely been working out on his own (he was reportedly working out at Boston College earlier this offseason), but without organized game action, it adds another element of uncertainty to the mix.

On the one hand, it’s only the end of February. On the other, it’s already the end of February. A deal sooner than later seems beneficial for both sides. Whether ultimately that deal comes with the Red Sox is, of course, the biggest question.

(Photo of Montgomery: Bailey Orr / Texas Rangers / Getty Images)

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