John Tomase

One final plea for Red Sox to sign Jordan Montgomery in free agency

There's still time for Boston to make a morale-boosting move.

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They say you don't often get a second chance in life, and the implication is clear: don't blow it.

But what about third, fourth, and fifth chances? Squander those, and as the saying goes that I just invented, you deserve to finish last for the third straight season.

Is it time for another Jordan Montgomery column? Why yes it is. If you're wondering why we've written so much about the free agent left-hander, it's because he was from Day 1 of the offseason the most obvious solution to the hole atop the Red Sox rotation.

He wouldn't earn as much as Yoshinobu Yamamoto, he didn't have as many durability concerns as Blake Snell, and he wouldn't cost draft pick compensation after being traded last season. Add the fact that he spent the entire bleeping winter working out in Boston while his wife conducted her residency at an area hospital, and Montgomery represented the easiest slam dunk since Jaylen Brown donned Michael Jackson's sequined glove at All-Star Weekend.

But so stubborn are the Red Sox in their refusal to devote even a single solitary resource to the 2024 squad, they've just let Montgomery sit under their noses all winter. Spring training games have already started, and still he remains unsigned.

It's time to move. With Cody Bellinger inking a below-market deal (three years, $80 million) to return to the Cubs this week, the remaining members of the Scott Boras Four should be packing up momentarily for Florida or Arizona, too.

And because we are either stupidly hopeful or hopelessly stupid, we're once again allowing ourselves to be sucked into the possibility of the Red Sox finally doing something, anything, to salvage the most demoralizing offseason of John Henry's tenure.

Per multiple reports – and confirmed by manager Alex Cora in Fort Myers – the Red Sox held a Zoom call with Montgomery on the eve of spring training. Whether that's just more eyewash or an actual sign that they finally intend to seize the good fortune scratching at their door remains to be seen.

"I think we're working," Cora told reporters, including MassLive. "We're working hard towards that. If it happens, it happens. If it doesn't happen, it doesn't happen. But we've been working hard the whole offseason. It's not lack of trying. I'm telling you. It's been a lot of meetings, a lot of conversations.

"Obviously (chief baseball officer) Craig (Breslow) has had a lot of conversations with agents. It's where we're at right now. We're still engaged with position players, with pitchers. We're trying to improve. And if there's an opportunity to do that, I bet we'll jump on it. But right now, it hasn't kind of like worked out or we haven't found a match."

The stars have aligned, if only the Red Sox would look up. Signing Montgomery erases their most egregious sin of the winter, gives them a legit starter to post atop their rotation, and perhaps most importantly, addresses the despair festering within the clubhouse.

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We are, after all, finishing a remarkable week that saw (A) CEO Sam Kennedy finally admit Breslow is working within a budget, (B) franchise icon Dustin Pedroia chide ownership for not signing anyone, and (C) star third baseman Rafael Devers effectively tell the front office to get off its ass or there's no point in playing the season.

Montgomery doesn't suddenly make the Red Sox World Series favorites, but his arrival would quell internal unrest and remind fans there's a reason to watch before Fenway Park houses the law offices of Mayer, Anthony, and Teel in 2026.

They've made late signings before. J.D. Martinez arrived in February of 2018 and immediately helped win a World Series. Shortstop Trevor Story didn't sign until March of 2022, and though that one hasn't worked out yet, he projects to play a key role this season.

Montgomery should've signed months ago, but his agent misread the market, which has created an opening the Red Sox frankly don't deserve. How many more chances do they expect to get at this? Make the obvious move. Show us you care or so help me god, we'll turn around and walk right out that door.

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