Yankees Eyeing Reunion with Jordan Montgomery Despite 2022 Trade Challenges

Montgomery Reflects on Unexpected Shift in Baseball Career

by Nouman Rasool
Yankees Eyeing Reunion with Jordan Montgomery Despite 2022 Trade Challenges
© Quinn Harris/Getty Images

The captivating saga of Yoshinobu Yamamoto's free agency has finally reached a climax, with the 25-year-old pitcher signing a staggering $325 million contract with the Los Angeles Dodgers. This high-stakes acquisition leaves several teams, including the New York Yankees, recalibrating their strategies.

The Yankees, in particular, are searching for a formidable pitching partner for Gerrit Cole. Amidst various potential candidates, Jordan Montgomery's name resonates the loudest, especially following his pivotal role in the 2023 World Series victory.

Jordan Montgomery, a seasoned pitcher with nearly six seasons under his belt with the Yankees, is no stranger to the 27-time World Series champions. This familiarity positions him as an ideal candidate for the Yankees. However, the lingering aftereffects of his unexpected 2022 departure from the team overshadow potential negotiations.

Despite this, a reunion could be on the horizon if both parties can navigate past the bitter remnants of their previous parting.

Montgomery's Emotional Trade Impact

Communication, or the lack thereof, often defines the trajectory of professional relationships.

In Montgomery's case, the surprise trade that transformed him from a Yankee to a St. Louis Cardinal, in exchange for Harrison Bader, left a notable impact. Montgomery expressed his shock and emotional attachment to the Yankees and highlighted the depth of his bond with the team.

A tangible sense of loss and nostalgia marked his subsequent encounters with his former team. Now, as the possibility of a reunion emerges, the Yankees and Montgomery stand at a critical juncture. A smooth departure in the past could have paved the way for an easier reconciliation, but the abrupt nature of their separation adds complexity to any potential agreement.

Despite this, reports from The Athletic’s Ken Rosenthal suggest internal discussions within the Yankees’ camp about welcoming Montgomery back. Montgomery's post-Yankees trajectory has only bolstered his value. His impressive record of ten wins and 166 strikeouts during the last season's league stages, coupled with his exceptional performance in the postseason, has significantly raised his stock.

This resurgence has reignited the Yankees' interest, but securing his return might prove challenging. However, the Yankees' recent strategic signings indicate a renewed determination, potentially signaling a shift that Montgomery might find appealing.

After a previous exit marred by miscommunication, a second chance offers an opportunity to rewrite their shared history and contribute to the Yankees' quest for another championship. The outcome remains uncertain with both parties yet to reach a definitive agreement.

The question now is whether the Yankees can rectify their past misstep or if it will continue to overshadow their future endeavors.