As the 2024 MLB postseason nears, several managers and executives are under intense pressure, potentially facing career-defining moments. October has historically been unforgiving—one misstep can alter a manager’s fate, as was the case with Grady Little in 2003, who was let go by the Boston Red Sox after a costly playoff decision. This year, some of MLB’s top leaders are in the spotlight as they guide their teams through the final stretch of the season.

Aaron Boone, manager of the New York Yankees, could be one such figure at risk. Despite leading the Yankees to the best record in the American League, the pressure to end the team’s championship drought—dating back to 2009—is enormous. If Boone, whose contract includes a club option for 2025, makes a key mistake that costs the Yankees in the postseason, his position could be in jeopardy. Owner Hal Steinbrenner will face a tough decision on whether to retain Boone or pursue a new direction.

On the West Coast, Dave Roberts, manager of the Los Angeles Dodgers, is similarly on the hot seat. Despite dealing with multiple injuries to the team’s pitching staff, the Dodgers are still expected to contend for a title. With just one year remaining on his contract, another postseason disappointment could spell the end of Roberts’ tenure. Though he collaborates closely with the front office, the responsibility for in-game decisions falls squarely on his shoulders.

For the San Francisco Giants, head of baseball operations Farhan Zaidi is feeling the heat as well. The Giants haven’t won a playoff series during his six-year tenure, and if they miss the postseason for a third consecutive season—despite exceeding the luxury tax—Zaidi could find his job in danger. His contract runs through 2025, but a lackluster finish could prompt ownership to reevaluate his role with the team.

Meanwhile, Skip Schumaker, currently with the Miami Marlins, has attracted attention as a potential candidate for managerial openings on the West Coast. His success over the past two seasons has boosted his profile, making him a sought-after name for future vacancies. At the same time, organizations like the St. Louis Cardinals and San Diego Padres are being closely watched, with Cardinals executive John Mozeliak nearing the end of his contract, and A.J. Preller of the Padres maintaining strong support despite the team’s struggles this year.

With the postseason looming, these managers and executives are facing critical decisions. October could prove to be a turning point for their careers, with each decision potentially shaping their futures in Major League Baseball.