Sep 17, 2025; Minneapolis, Minnesota, USA; New York Yankees designated hitter Aaron Judge (99) celebrates scoring a run against the Minnesota Twins during the first inning at Target Field. Mandatory Credit: Nick Wosika-Imagn Images
The Major League Baseball (MLB) postseason is upon us, set to begin on October 3, 2023, and the stakes couldn’t be higher for the league’s superstars. As the focus shifts to the playoffs, players face immense pressure to perform, which can significantly impact their legacies. A strong postseason can elevate a player’s status, while a lackluster performance may lead to scrutiny and debate during Hall of Fame voting seasons.
Defining Legacies in October
Consider the case of Clayton Kershaw, the Los Angeles Dodgers left-hander who boasts a remarkable career record of 222-96 and a 2.54 ERA. Despite being a three-time NL Cy Young Award winner and an 11-time All-Star, Kershaw’s postseason struggles—his record stands at 13-13 with a 4.49 ERA over 39 playoff games—have raised questions about his Hall of Fame worthiness. Many argue that postseason statistics should serve as tiebreakers rather than definitive factors in a player’s legacy. The pressure is palpable, especially as the Dodgers aim for a championship.
As teams prepare for the postseason, we assess the pressure on key players from each playoff roster, focusing on how their performances could shape their reputations.
Stars Under Pressure
1. **Aaron Judge, New York Yankees**: The Yankees are in dire need of a World Series title, their last victory dating back to 2009. While Judge’s individual accomplishments are impressive, including his record-setting 62 home runs in 2022, securing a championship is crucial for his place in Yankees history.
2. **Vladimir Guerrero Jr., Toronto Blue Jays**: Guerrero recently signed a $500 million, 14-year contract extension that takes effect next year. A World Series title this postseason would significantly enhance his stature within the game and help attract further talent to Toronto.
3. **Jose Ramirez, Cleveland Guardians**: Known as J-Ram among baseball aficionados, Ramirez’s elite skills remain underappreciated by the general public. Winning a championship could elevate his visibility and legacy in the sport.
4. **Manny Machado, San Diego Padres**: With a reputation that has been somewhat inconsistent, Machado needs a postseason highlight to anchor his career and solidify his status among the game’s elites.
5. **Tarik Skubal, Detroit Tigers**: Likely on the verge of winning his second AL Cy Young Award, a successful postseason performance could establish Skubal as one of the best pitchers of his generation.
6. **Kyle Tucker, Chicago Cubs**: After a moderate regular season, Tucker needs a standout postseason to redeem himself and bolster his free agency prospects as he heads into the offseason.
7. **Alex Bregman, Boston Red Sox**: Bregman, who can opt out of his three-year, $120 million contract after this year, is positioned to elevate his value significantly with a strong playoff run.
8. **Kyle Schwarber, Philadelphia Phillies**: Known for his power hitting, Schwarber has the opportunity to make a name for himself this postseason, potentially leading to a lucrative contract.
9. **Elly De La Cruz, Cincinnati Reds**: A dynamic player with significant potential, De La Cruz’s ability to disrupt games could play a crucial role in the Reds’ postseason aspirations, even as he has one more pre-arbitration year remaining.
10. **Shohei Ohtani, Los Angeles Dodgers**: Ohtani has already solidified his legacy as one of the game’s greatest talents. With his contract situation looming, the postseason could further enhance his already stellar profile.
11. **Christian Yelich, Milwaukee Brewers**: The 2018 NL MVP has a solid legacy, but adding a championship ring would enhance his already impressive career.
12. **Cal Raleigh, Seattle Mariners**: Though he is seen as a one-hit wonder, Raleigh, under contract through 2030, could benefit from a breakout postseason that could redefine his trajectory.
As the postseason unfolds, the spotlight will be on these superstars as they chase not only a championship but also the enduring legacies that come with it. Each player’s performance will be scrutinized, and the outcomes could resonate far beyond October, shaping their careers for years to come.
