One man’s master plan is another one’s mega dud. This season the Los Angeles Dodgers showed the complete power of deferrals. So it was only a matter of time before others tried their luck on something similar. But one method cannot work every time, the New York Yankees’ pursuit of Jordan Montgomery has just proven that fact beyond any doubt.

While until now it looked like the New York Yankees’ payroll troubles were the reason for their failure, it seems the story goes deeper than initially imagined. In their bid to do what the Dodgers did, the Bronx Bombers might have overplayed their hands. Not just that, they may have actively pushed Monty toward the Arizona Diamondbacks.

Top insider Jim Bowden has revealed that the Yankees’ offer for Montgomery was laden with deferrals. Bowden said the deferrals were around “15-20 plus years.” This pretty much means that the Bronx Bombers had offered their former member a multi-year contract. However, due to their 110% taxation issue, the team asked him to defer that amount to some other time.

The key issue stems from the fact that the AAV was “much less” than the D-Backs’ $25 million deal that Montgomery eventually signed. While that is a disappointing ending, it once again shows how the Yankees may have overextended themselves this offseason. With the team not able to make any more signings, they’re entering this season with a pitching staff sans Gerrit Cole. 

However, one wonders whether this prudence of the Yankees might be a way to get themselves ready for the 2024-25 offseason. Could the lack of free-agent signings other than Marcus Stroman be a way to save for Juan Soto?

Unwilling to risk Juan Soto for Jordan Montgomery?

The Yankees currently sit above the highest tax threshold of $297 million. This pretty much means that they would’ve had to pay a 110% tax on Montgomery’s salary. So at $25 million, Monty would’ve cost the Yankees $52.5 million. Perhaps Hal Steinbrenner wouldn’t have wanted to spend that much when he’s staring at a major battle next season for Juan Soto. 

Soto’s free agency is bound to garner interest from all over the league. The 25-year-old’s unique position as a youngster with high experience has made him a league favorite. As a result, it wouldn’t be surprising if a bidding war ensues for the superstar. In that case, wouldn’t the Yankees like having all the flexibility they can have? Could this just be preparation for that? What if this was the master plan all along? That would make more sense than low-balling a Montgomery right before a make-or-break season in a season where the pitching market is drying up quickly.

Read more: Jordan Montgomery Deal Sows Discord Among Yankees Fans, Front Office Accused of Penny-Pinching