John Mozeliak and Brian Cashman are evidence of holding onto leadership for too long

The New York Yankees and St. Louis Cardinals are the two most storied franchises in Major League Baseball history. The organizations rank first and second in World Series championships all-time and have represented what winning baseball looks like for generations of fans.

Except for the generation of fans growing up right now, who have only known the disappointment and struggles that have come with the franchises as of late.

There is no doubt that the Yankees are still the biggest brand in baseball and that the Cardinals are still viewed as a historic franchise in baseball history. Baseball fans have still expected these two organizations to find ways to win, and yet, both have failed to live up to expectations for over a decade.

There are a lot of differences between these two franchises. The Yankees are in the biggest market in the United States and will always be able to dwarf the payroll of the Cardinals. Cardinals fans can point to the fact that the Yankees still have names like Aaron Judge and Juan Soto, and yet, if you were to listen to fans of both teams, there has been overall discontentment with the leadership in the organization for some time now.

Yankees' Brian Cashman and Cardinals' John Mozeliak are the longest-turned baseball executives in today's game. Cashman has been in charge of the Yankees baseball operations since 1998, while Mozeliak took control of the Cardinals in 2007. The beginning of both of their tenures was exceptional, but the latter years have been, well, frustrating at best.

Cashman won three straight World Series to begin his leadership and collected another title in 2009. The Cardinals, under Mozeliak, won the World Series in 2011 and went to the NLCS or World Series every year from 2011-2014. But since those glory days, neither have found much success.

The Yankees have not appeared in a World Series since 2009, and the Cardinals have not been back to the October Classic since 2013. With each passing year, fans grow more and more weary of the current front office and the ownership group supporting them.

Yankees fans have been able to enjoy some big swings from the front office in this down period, such as signing Gerrit Cole, extending Aaron Judge, and trading for names like Juan Soto and Giancarlo Stanton, but those are the kinds of moves you expect the Yankees to make, and their fans still hold winning as the true standard for Yankee baseball.

Mozeliak has made his own fair share of aggressive moves, trading for Marcell Ozuna (and having a deal in place for Stanton before that), as well as trading for the duo of Paul Goldschmidt and Nolan Arenado. The front office also threw big money deals unsuccessfully at David Price and Jason Heyward, while locking in guys like Willson Contreras and Sonny Gray.

Both seem to be embracing some sort of succession plan in the near future. It is widely expected that Mozeliak's will begin this offseason and run through the end of the 2025 season in some sort of fashion, while people are also speculating that Cashman will be succeeded by Kevin Reese following the 2026 campaign.

In the case of both executives, fans seem to be at their wits' end. Even with the Yankees playing at a high level, fans of the team seem to be overwhelmingly against Cashman continuing to lead the organization. Cardinals fans know the frustration with Mozeliak all too well.

Mozeliak and Cashman have arguably done more damage in the stretch of their career than good for their own legacies, and both organizations seem like they are well overdue for some changes in who calls the shots. A strong finish to the 2024 season could do wonders for Cashman's standing with Yankees fans, but Mozeliak seems like he is out of time to "fix" the things fans have grown weary of.

Both executives will end up in their organizations' Hall of Fames and will be seen as two of the better front-office leaders in baseball history, but their status could have been more secure had they finished stronger or transitioned power much sooner.