The Boston Red Sox of today are quite unrecognizable from yesteryears. It seems like yesterday when they were at the top of the league (4 World Series this century), had a competitive payroll, and were an attractive option for every player. The issue isn’t so much their lost competitiveness but that the Sox look disinterested in returning to their best. It’s become obvious to their recent dealings with Jordan Montgomery.

Montgomery’s been the primary link of the Boston Red Sox since early November. However, talks have never progressed past the initial getting-to-know-each-other stage. Partly because of high demands and partly due to the unwillingness to spend money, things have stalled. Now, if reports are to be believed, the Red Sox might be looking in another direction as well.

Jordan Montgomery finds himself at a crossroads this late in the offseason

For Jordan Montgomery, his free agency couldn’t have come in at a worse time. Normally a pitcher entering the market after having played a heroic role in his team’s World Series win commands a huge price. But this was the year when multiple teams decided to curtail their payrolls leading to a slow market. The Boston Red Sox are also one such team, as Jon Heyman of the New York Post reports. 

Heyman reported that the Red Sox management held a Zoom call with Montgomery three weeks ago and is still in touch. But things haven’t moved forward between the two parties. “They seem disinclined to the seven-year deal Montgomery seeks, and some still believe a short-term innings-eater (Michael Lorenzen or Mike Clevinger?) may be more likely,” said the report. 

That is a big development in this story. Until now, the Red Sox looked to be in prime position to sign Monty, but this changes things up. The Sox believe they only need a short-term pitcher and Montgomery’s stance toward a shorter deal isn’t quite clear. So in that scenario, could the BoSox look elsewhere? That would certainly prove to be a major blow for the pitcher.

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Talking internally, the recent injury to Lucas Giolito has opened up a huge pitching gap in the Red Sox. While Montgomery can fill it, the Red Sox’s unclear plan has made things complicated.

Boston Red Sox’s vague strategies complicate the links?

On one hand, the Red Sox are completely focused on their farm system. But on the other hand, they signed an experienced hand like Lucas Giolito to a two-year $38 million deal. Now Giolito might miss at least one year owing to his partially torn UCL and flexor strain. However, even after his injury, the team would rather have a short-term pitcher than a long-term one.

As a result, instead of Monty, their interest may go toward Michael Lorenzen or Mike Clevinger. Or maybe Scott Boras can convince Montgomery to accept a short-term deal with opt-outs and bet on himself. Two of his clients have already done it. There’s a chance that Montgomery could be next. But until then, as it stands, a short-term deal (or maybe trade) looks to be the way forward for the Boston Red Sox.

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