Droppin’ Dimes: Remembering the Yankees who won’t be in pinstripes for the 2024 World Series

For the first time since beating the Philadelphia Phillies in 2009, the New York Yankees are going back to the World Series. In the 15 years since their last appearance, the Yankees have turned over an entirely new roster, loaded with some of the best talent baseball has to offer. It will be the first World Series appearance for some of the teams’ stars, Aaron Judge, Giancarlo Stanton, Gleyber Torres and others. Yet, there are players no longer with the organization who have significantly contributed to the Yankees’ long journey to get back to the World Series. These players helped cultivate a new culture in the Bronx and have provided fans with unforgettable moments over the years. 

Brett Gardner  

Unlike the rest of this list, Brett Gardner has gotten to bask in the limelight of winning a World Series. He debuted for the Yankees in 2008 and was a part of the team that defeated the Phillies in 2009. Being so early in his career, Gardner had a much smaller role with the team during this run. In 2010, he became a consistent starter, batting .277 and stealing 43 bases through 150 games. In the following year, he stole a career high of 49 bases. His competitive personality provided a fiery spark, always speaking his mind. Gardner will be remembered as a bridge between eras. As the greats of the 2009 Yankees slowly went their separate ways, Gardner remained the final link to that championship team. Before long, a new wave of Yankee stars had come into the fold. Judge credits Gardner as being a leader and helping to prepare the next generation of Bronx Bombers.  

“What this guy meant inside this clubhouse, the things he taught me about being a leader and trying to treat people with respect — even what I observed from him and how he treated people. I don’t want people to forget that” Judge said. 

Gardner retired in 2022 as the last player to retire from his championship team. Judge still pays homage to his former teammate today during the Yankee Roll Call, flexing at the bleachers, just like Gardner did. 

Didi Gregorius 

No one had bigger shoes to fill than Didi Gregorius coming to the Yankees in 2015 as the new starting shortstop. When Derek Jeter retired in 2014, it left a massive void in the hearts of Yankees fans. Jeter was a New York icon, serving as the 11^th captain in the franchise’s history. He won five World Series with the Yankees and forever redefined what it meant to be the starting shortstop in New York. Gregorius was given the impossible task of following in these footsteps. He struggled under this weight in the early months of his Yankee tenure. However, he was able to win over the hostile New York crowd with his hard work ethic and his growth as a hitter. Gregorius had a .277 batting average while knocking 20 or more homeruns from 2016-2018. Gregorius made his mark in the Bronx during the 2017 playoffs, a run that will live in infamy for Yankees fans. In the AL Wild Card game, Gregorius hit a game-tying three-run homerun igniting a comeback victory over the Minnesota Twins. He followed this up in the ALDS, by hitting two homeruns off the Cy Young winner Corey Kluber in game five to secure the series victory. Following the 2019 season, where he struggled to recover from injury, the Yankees decided not to re-sign Gregorius. He entered free agency that off-season, signing with the Phillies. He played three seasons with them before retiring in 2022 at age 32. 

Masahiro Tanaka  

Masahiro Tanaka debuted for the Yankees with high expectations. He was a phenom in Japan’s Nippon Professional Baseball, signing a seven-year 155 million contract. He immediately met those expectations. Tanaka was lights out through his first 14 starts, earning an 11-1 record while keeping a 2.10 ERA. He dominated with his splitter and seemed to have near perfect control over his pitches. Unfortunately, he suffered a partial UCL tear during his rookie campaign. Despite the initial concern over his longevity, Tanaka decided to go through rehab instead of Tommy John surgery and miraculously avoided any major surgeries during his Yankee career. While he didn’t get back to the same level of dominance he had in his rookie season, Tanaka was one of the New York’s most reliable starters. He posted a 78-46 career record with a 3.74 ERA. Where Tanaka separated himself was in the playoffs. In his postseason career, he made ten starts with a 3.33 ERA. During the 2017 playoffs, he made three starts and had a stellar 0.90 ERA. After the 2020 season, Tanaka decided to return to his former team, the Tohoku Rakuten Golden Eagles in Japan. Tanaka left an everlasting impression on New York fans of professionalism and consistency.  

Gary Sánchez 

Gary Sánchez burst onto the scene for the Yankees in 2016. “The Kraken” hit 20 home runs in just 53 games played, earning him a runner-up finish in American League Rookie of the year voting. In 2017 he followed up his impressive rookie campaign by hitting 33 homeruns, emerging as one of the best offensive catchers in baseball and receiving his first All-Star selection. Alongside Judge and Torres, the “Baby Bombers” era in New York had begun. After the explosive start to his MLB career, Sánchez’s production became inconsistent. Injuries and bad plate discipline led to a decline in his statistics. While he still could tear the cover off the ball if he got a hold of one, he became too much of a boom-or-bust player. Playing in New York comes with intense scrutiny from both the fans and the media, and with his performance dwindling he became a lightning rod for criticism. His poor defense and, at times, utter laziness turned the fans against him. At the same time, his raw talent had fans hoping he could return to the player he once was. The Yankees traded Sánchez to the twins in 2022, and his potential seemed to be missed by that point. Despite how it all ended up for him, Sánchez gave Yankees fans some incredible highlights.