Loved by their fans and hated by nearly everyone else, the New York Yankees have a unique reputation in baseball as the most accomplished franchise in history. Past generations of fans have witnessed the Yankees win countless titles. However, the current generation of Yankees fans have endured a drastically different experience.
The Yankees have struggled, getting eliminated in the first round of the playoffs in 2015 and missing the playoffs again in 2016. 2017 marked the start of a new era in the Bronx. In his rookie season, Aaron Judge smashed 52 home runs and led the Yankees through a deep postseason run. New York notched a comeback win in the Wild Card to defeat the Minnesota Twins before upsetting the top seed Cleveland Indians in the American League Divisional Series (ALDS). In the best-of-seven American League Championship Series (ALCS), the Yankees took a three games to two lead over the Houston Astros before losing the last two games. While the 2017 season ended in heartbreaking fashion, it introduced young Yankees fans to the euphoric experience that was winning in the playoffs.
After 2017, Yankees fans endured a brutal stretch as they watched the team suffer playoff eliminations from the Boston Red Sox in 2018 and 2021, the Astros in 2019 and 2022, the Tampa Bay Rays in 2020 and missing the playoffs in 2023. Throughout this period, the Yankees never came closer to a World Series appearance than they did in 2017.
After missing the playoffs for the first time in the Aaron Judge era, the Yankees front office made a monumental move before the 2024 season. The San Diego Padres traded Dominican superstar Juan Soto to New York, adding serious firepower to their offense. The trade paid off as Soto clubbed a go-ahead home run in the deciding game of the ALCS to send the Yankees back to the World Series after 15 years. Oftentimes when younger Yankees fans tout the teams league leading 27 championships, they are reminded that they were either not alive or merely toddlers the last time New York won it all. This was the Yankees’ best chance yet to provide the new generation with a championship memory of their own, and they failed. The Los Angeles Dodgers defeated the Yankees in five largely uncompetitive games. With each year’s painful closure, fans have come to expect traumatic experiences come October.
So where have the Yankees gone wrong? How has the organization only managed one championship in the last 24 years? Run by the Steinbrenner family, the Yankees consistently have one of the biggest budgets in the league, spending well over $200 million on player contracts. Each offseason, the front office signs talented free agents and makes blockbuster trades that lead fans to expect championship-level baseball. Despite the high spending, the Yankees front office has failed to construct strong overall rosters.
Take the 2020 season for example, while the Yankees acquired elite pitcher Gerrit Cole on a nine year contract, they made no notable additions to the offense. Aside from outfielders Aaron Hicks and Brett Gardner, no other Yankees starters were left-handed hitters. This proved to be a massive weakness in the playoffs when the Rays pitching staff dominated New York’s poorly structured lineup.
Another instance of an incomplete roster compromising the Yankees occurred over the last two seasons. This was when the Yankees acquired utility player Jazz Chisholm Jr. from the Miami Marlins and stationed him at third base. Chisholm had no experience playing third and struggled throughout the 2024 season. With no other choice but to move Chisholm away from third, New York needed a new third baseman. Rather than exploring free agency or the trade market, the Yankees reassigned utility player Oswaldo Cabrera to third. This move limited Cabrera’s contributions to the team, as his greatest strength was his ability to play numerous positions.
A topic of debate amongst fans is whether manager Aaron Boone is merely a puppet of the front office. Fans speculate that the Yankees analytics department and front office have Boone manage based on their predetermined strategy rather than managing with his intuition. However, fans constantly demand Boone be fired, contradicting their theories about the Yankees’ management.
Compared to most sports fanbases, Yankees fans are spoiled. It has been over 30 years since New York last had a losing record. The team rarely misses the playoffs. The fans’ high standards don’t only stem from New York’s winning history, Yankees ownership are vocal about their championship aspirations. Owner Hal Steinbrenner has said on numerous occasions that a season that doesn’t end with a World Series title is a failure. Through Aaron Judge’s first eight years with the team, he has played out a career that some already consider to be Hall of Fame worthy. With six years left on Judge’s contract, the Yankees have a window of opportunity to build a championship caliber team around their star. If they don’t succeed, the Aaron Judge era will be looked back on by fans as the single worst wasted opportunity in Yankee history.
