One more request that Jordan Montgomery be signed by the Red Sox in free agency

Mike Felger and John Tomase speak about Alex Cora’s recent remarks, the Red Sox’s current situation, and whether or not he gives them motivational speeches throughout Spring Training.


It’s frequently said that you don’t get second chances in life, so the lesson here is to make the most of it.


However, what about possibilities three, four, and five? Waste those, and you’re deserving of finishing last for the third season in a row, to use the phrase I just made up.


When will there be a new Jordan Montgomery column? Yes, it is, for sure. If you’re wondering why we’ve written so much about the left-hander who is a free agent, it’s because he was the most obvious answer to the top hole in the Red Sox rotation from the first day of the summer.


He wouldn’t cost a draft selection after being traded the previous season, he wouldn’t make as much as Yoshinobu Yamamoto, and he didn’t have as many durability issues as Blake Snell. When you consider that Montgomery worked out in Boston for the whole winter while his wife was doing her residency at a local hospital, it was clear that Montgomery was the easiest slam dunk since Jaylen Brown wore Michael Jackson’s glittery glove to All-Star Weekend.


However, the Red Sox have been so obstinate that they have chosen to ignore Montgomery throughout the winter rather than commit even the slightest amount of resources to the 2024 team. Games for the spring training camp have already begun, and he is still unsigned.


Now is the time to relocate. With Cody Bellinger signing a three-year, $80 million deal below market value to rejoin the Cubs this week, the other three members of the Scott Boras Four ought to be packing their bags and heading to Florida or Arizona as well.


And once again we’re letting ourselves get carried away by the idea that the Red Sox might finally do something, anything, to turn around the most disheartening offseason of John Henry’s tenure because we’re either hopelessly foolish or naively hopeful.

As per many accounts, which manager Alex Cora in Fort Myers verified, the Red Sox and Montgomery had a Zoom conversation the night before spring training began. It remains to be seen if that’s just more spin or a real indication that they really do want to take advantage of the good fortune knocking on their door.


As Cora stated to reporters, including MassLive, “I think we’re working.” “We’re putting a lot of effort into that. When it occurs, it occurs. It isn’t happening if it doesn’t. However, we have spent the entire summer working hard. It’s not for lack of effort. I am informing you. There have been numerous meetings and discussions.


“Craig Breslow, the chief baseball officer, has undoubtedly spoken with agents frequently. That’s our current situation. Pitchers and position players are still our focus. We’re working to get better. And we’ll definitely seize the chance to do that if it presents itself. However, as of right moment, nothing has really worked out or a match has been found.”


If only the Red Sox would look up, the stars would have aligned. By signing Montgomery, they atone for their worst wintertime mistake, add a reliable starter to the top of their rotation, and—possibly most importantly—take care of the hopelessness that has been brewing in the clubhouse.


We are, after all, coming to the end of an incredible week that saw (A) team legend Dustin Pedroia chastise ownership for not signing anyone, (B) CEO Sam Kennedy finally acknowledge that Breslow is operating within a budget, and (C) star third baseman Rafael Devers effectively tell front office to get off its ass or there’s no point in playing the season.


Although Montgomery doesn’t instantly make the Red Sox the favorites in the World Series, his arrival would calm tensions among the team and give supporters one more incentive to follow before Mayer, Anthony, and Teel’s legal offices move into Fenway Park in 2026.

They had previously signed late. When J.D. Martinez arrived in February 2018, he contributed right away to the World Series victory. Trevor Story, a shortstop who signed in March 2022, is expected to be a major player this season even though things haven’t worked out yet.


Montgomery ought to have signed months ago, but his agency misjudged the market, creating an opportunity that, to be honest, the Red Sox don’t deserve. How many more opportunities are they hoping for to pull this off? Take the obvious action. Please show us that you care, or else we’ll turn around and leave by that door.


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