How does John Mozeliak stack up against other long-term general managers?

Brian Cashman, New York Yankees -- February 3, 1998

Brian Cashman has overseen now 4 decades of Yankee baseball now. He is far and away the longest-tenured head of baseball operations for any team in baseball, and he has seen just about everything a baseball executive can see.

While other smaller franchises must work within certain financial confines, Cashman has largely been given blank checks to sign for players he wants. Cashman was able to poach talented players from other organizations in the early 2000s, and he's been able to acquire superstars like Alex Rodriguez, Gerrit Cole, and Juan Soto, among others.

It's tough to mess up when given complete financial freedom to build a talented team. Therefore, Cashman almost needs to be judged on a different scale, but alas, the purposes of this exercise deem him a valid player.

League parity has made it more challenging for teams to continually win World Series the way the Yankees did in Cashman's first 3 years. The Yankees of the late 90's and early 2000's were a formidable team. They went to 5 World Series within 6 years, and they won 3 of them. Money played a big factor in Cashman's success early on, but as teams have figured out to use data more effectively, the Yankees have seen a drop in success.

In 10 more years at the helm, Cashman has had double the amount of playoff appearances and division titles than John Mozeliak. The World Series comparison isn't close, although neither baseball ops leader has had a team make it to the Championship Series since 2019. In fact, the Cardinals have made the World Series more recently than the heralded Yankees.