The New York Yankees are synonymous with baseball excellence but it comes with a twist. The Pinstripers have a historic legacy, however, certain aspects of the mega-franchise are questionable this season.  A past trade involving Jordan Montgomery has resurfaced, raising eyebrows about his unceremonious trade. After all, it led him to say the words, “I didn’t really have much faith in my heater at the Yankees”.

For New York, nurturing homegrown players has always been key. However, the abrupt departure followed by certain remarks from Montgomery presents a narrative that demands attention. His revelations about the constraints he felt in the Big Apple pose a serious question. Will history play a part in the Yankees’ free agency pursuits this offseason?

Will the New York Yankees’ Past Trade Haunt Them? 

The Yankees are grappling with roster decisions this off-season, especially after delivering a disappointing 82-80 season this year. While certain moves like acquiring the one-year rental Juan Soto are optimistic, their future free agency strategies might be doomed, thanks to their not-so-great past with Montgomery. His 2022 revelations were, “I had been told that it wasn’t that good compared to my other pitches, and if I was gonna get hit, it was gonna be on a curveball or changeup, which isn’t how you can pitch.” This definitely added a layer of complexity for NYY to recruit Monty.  

His opinion regarding the team’s comments on his fastball usage and the evolution of this pitch into one of his strengths highlights a clear disconnect. Although the organizational directives and player capabilities have not been on the same page, Montgomery expressed belief in being a ‘Yankee for life’. He expressed his current sentiments toward the team, “When you come up homegrown they take care of you, and not everyone can pitch in Yankee Stadium”. 

To add to it, the 31-year-old’s reflections go beyond personal experiences, indicating a new perspective on the Yankees’ recruitment strategies. Nevertheless, the chances of a union with the former team remain uncertain. That said, his honest insights about the challenges of pitching in New York versus St. Louis are worth diving deep into. Will this too affect the club’s chances of reuniting with him? 

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After Struggles in the Bronx, what Does Montgomery’s Resurgence in St. Louis Speak of the Yankees? 

When Monty stepped onto the mound in New York, the pressure of the pinstripes weighed him down. In an episode of Ryan Ruocco and CC Sabathia’s ‘R2C2’ podcast, he stated, “I was always worried about getting booed off the mound in New York. The pinstripes are heavy. Not everyone can handle it. I feel like I handled it OK.” Such sentiments give a glimpse of the pressure and scrutiny that accompany playing for one of baseball’s most storied franchises.

Read More : Is a Yankees Reunion With Jordan Montgomery Possible? Or Will His 2022 Trade be an obstacle?

Contrastingly, Montgomery’s transition to the St. Louis Cardinals has been nothing short of transformative. He boasted a stellar 5-0 record with a 1.45 ERA in seven starts. Additionally, he appeared revitalized, free from the expectations that defined his tenure with the Yankees. His rise to fame in St. Louis, displayed as dominant performances against his former team, speaks volumes of the impact the environment can have on a player. Will the MLB world see Monty in the pinstripes? One can only wait and watch.