Red Sox Set to Miss out on Jordan Montgomery? Boston Team’s Free Agency Misfortune Continues

It’s common for people to yell “Kobe!” after making a perfect shot. For baseball fans, it might be right to yell “Red Sox!” when you miss one. The Boston Red Sox have been missing some of the biggest free agents this offseason. The list includes the likes of Yoshinobu Yamamoto, Teoscar Hernandez, and Shota Imanaga among others. But amidst all of these misses, there was one ray of light – Jordan Montgomery, now even that is turning bleak.

The talks between Montgomery and the Red Sox have continued on since November. The interest was always mutual but the Sox have failed to close the deal. Call it a budget issue or a vision mismatch, things have stalled in this connection. Is there a positive end to this struggle or are the Sox about to lose another race?

Jordan Montgomery and Boston Red Sox’s complicated love story 

The links first began when Montgomery shifted to Boston to accompany his wife. Ever since then, it became obvious that the Red Sox had an advantage in the Monty sweepstakes. However, until that time the Texas Rangers were firmly in the race as well. But then by January, it became obvious that the Rangers’ monetary issues were too big to ignore, and suddenly Beantown became the place to be for Monty. However, things have changed since then.

Jon Heyman of the New York Post revealed that the Boston Red Sox weren’t interested in a long-term deal with Monty. They preferred a “short-term innings eater” instead. Reportedly the World Series Hero was looking for a seven-year deal. While it isn’t long for a 31-year-old, the Red Sox’s youth push makes a deal like that highly unsuitable.

Evidence of that strategy is the latest extension that the Red Sox offered to their young ace Brayan Bello. ESPN’s Kiley McDaniel first reported that he had signed an extension worth $55 million. Then MLB.com’s Mark Feinsand remarked that it also includes a 7th-year $21 million option. So where does a long-term deal for Montgomery fit in this youth push? Logically there is no fit.

Read more: Top MLB Teams That Need Blake Snell and Jordan Montgomery, as MLB’s Pitching Market Declines

Perhaps that’s why doubts are beginning to emerge about the future of the Monty-Sox connection. Is a short-term deal a possibility at this stage for the pitcher? 

Another short-term solution in store for a Scott Boras client?

According to Jon Heyman, while Blake Snell is fine with a short-term deal with opt-outs, Montgomery still seeks a long deal. While reasons weren’t given, one can speculate on why the pitcher doesn’t want to enter the market next year again. It could be that, unlike Snell, Monty’s market won’t change much next season. 

On the other hand, a short-term deal would entail a front-loaded structure. Will the famously financially prudent Red Sox ownership part ways with so much money for a single year? That would certainly be a surprising development. However, it will not be as surprising as the fact that it’s 10th March, and both Scott Boras star pitchers do not have a home yet.

Read more: “Better Than What People Think”: Confident Alex Cora’s Walk Year Last Chance to Sell Red Sox on Long-Term Fit