Daily online updates continue to suggest that the Yankees organization is ready to cease discussions regarding Cody Bellinger’s contract. The team reportedly maintains its original five-year proposal, valued around $150 million, extended to the former MVP since free agency began. Bellinger’s representatives, however, reportedly remain convinced they can secure a seven-year commitment. Reports indicate that the Blue Jays and Mets are also in talks with Bellinger’s representatives, and the Yankees are seemingly prepared to allow a divisional or local competitor to sign him if the cost exceeds their current offer.
The team’s reported shift in strategy mainly focuses on the trade market, with significant interest expressed in Freddy Peralta, a pitcher for the Brewers, despite acquiring Ryan Weathers recently (Austin Hays is also mentioned as a less prominent outfield prospect). In my view, the Yankees require substantial reinforcements, particularly since the Blue Jays, Red Sox, and even the Orioles appear stronger on paper compared to their previous season. New York’s success hinges on several optimistic scenarios materializing: Gerrit Cole performing well in his 35th year post-Tommy John surgery, Jazz Chisholm Jr.’s outstanding 2025 season reflecting his true ability, Austin Wells demonstrating his 2024 form rather than his previous year’s performance, and Aaron Judge sustaining what could be considered the most impressive peak of any right-handed batter in history.
The acquisition of Peralta, and particularly Bellinger, would mitigate some of these potential risks. Without Bellinger, the Yankees’ batting order appears quite weak—noticeably more so than their pitching staff. This forces reliance on improvements from Anthony Volpe and Jasson Domínguez, or Trent Grisham maintaining his performance, or Spencer Jones developing into a legitimate Major League player, with each of these outcomes seeming equally improbable. Although I believe Cody Bellinger has moved past his MVP-caliber performance, I would reasonably anticipate him outperforming all four of those individuals in the 2026 season.
However, this is where the situation becomes complicated. A five-year deal is likely my maximum for Bellinger, and I would anticipate the final year’s performance to be significantly below expectations. Extending the contract to six or seven years would transform a single season of diminished output into a protracted, frustrating situation reminiscent of Aaron Hicks’ tenure. Nevertheless, every personnel and roster choice made by the Yankees must be evaluated in the context of achieving success alongside Aaron Judge. The duration of having a player with a 200 wRC+ and 10-WAR output, currently ranked as the second-best hitter and seventh-most valuable player in the history of the sport’s most legendary franchise, remains uncertain.
The sentiment that “the playoffs are a matter of chance” is frequently echoed, and the organization seemingly subscribes to this idea. The strategy involves assembling a team strong enough to reach the postseason, reinforcing the bullpen heavily, and then observing the outcome. Within a diluted playoff format, and considering an American League that appears less challenging than the National League, the Yankees, in their current configuration, are likely a postseason contender unless a major disaster occurs. Moreover, it’s a playoff team that would present a formidable pitching rotation for opponents in the postseason.
However, one crucial aspect the organization hasn’t fully adopted throughout nearly a decade of “Baby Bombers” era baseball is this: while the postseason indeed contains considerable unpredictability, it’s possible to mitigate those risks. The Dodgers narrowly avoided a World Series defeat due to a crucial base-running decision by an opponent – an example of such randomness – yet they consistently invest significant effort and resources to enter the playoffs with the strongest possible roster, a strategy that has proven effective over the past two seasons.
While certain factors will inevitably lie beyond one’s influence, many aspects remain within one’s dominion. The upcoming two free agency periods appear notably thin in talent, with prominent names like Nico Hoerner and Randy Arozarena seemingly being the best options in the 2027 class. There isn’t a strategy of “delaying a year for a specific player” on the horizon, and with a potential labor dispute looming next year, that presents another possible unproductive year during Aaron Judge’s prime. He is already considered by some to be the most outstanding Yankee without a championship, and failing to re-sign Cody Bellinger or secure a comparable player to provide similar supplementary output significantly increases the probability of that championship drought continuing.
