Ex-Pirates exec finds playoff success in Seattle, and it’s painfully familiar

Trevor Gooby spent more than a decade in the Pittsburgh Pirates organization, rising through the ranks as one of their most respected baseball operations and ballpark executives. He helped oversee everything from fan experience to spring training operations, earning a reputation for competence and professionalism – two qualities the Pirates have often struggled to project under owner Bob Nutting’s leadership.

Now, Gooby is the executive vice president and chief marketing officer of the Seattle Mariners, who are one win away from their first World Series berth in franchise history. In a recent interview with Jason Mackey of the Pittsburgh Post-Gazette, Gooby was very respectful and complimentary of the Pirates organization for the role it played in his career development, but Pittsburgh fans can't help but see the underlying pattern here.

When Gooby left for Seattle, it was yet another example of the Pirates losing capable people to organizations with stronger infrastructure, better resources and a genuine commitment to winning. Now, as the Mariners enjoy sustained success and a postseason berth with Gooby playing a key role in their off-field operations, it feels like déjà vu for Pittsburgh – watching another talented baseball mind flourish somewhere else.

Former Pirates exec finding playoff success with Mariners feels painfully familiar for Pittsburgh fans

This pattern isn’t new. The Pirates have a long history of seeing their best and brightest thrive after leaving the organization – from players like Gerrit Cole and Tyler Glasnow to front-office figures like Neal Huntington’s lieutenants who have since found new homes. It underscores a systemic problem: Pittsburgh can identify good people, but it can’t seem to keep them, nurture them or build an environment where success is sustainable.

Gooby’s trajectory mirrors that of countless players who blossomed after escaping PNC Park – only this time, the loss isn’t measured in home runs or ERA, but in leadership and institutional competence.

At its core, Gooby’s success elsewhere is an indictment of the Pirates’ organizational culture. In Pittsburgh, ambition often seems capped by budget and bureaucracy. Talented individuals hit a ceiling, realizing their professional growth – or their chance to be part of a winner – must come elsewhere. Seattle gave Gooby what Pittsburgh couldn’t: a forward-thinking environment that rewards initiative and prioritizes progress.

For fans, it’s a bitter but familiar pattern, and another reminder that the Pirates’ problems go deeper than roster construction. It’s a cultural rot, one that drives away good people and leaves the organization constantly rebuilding both its team and its identity.

Gooby’s postseason success with the Mariners is more than just a nice career story. It’s a painful reminder of a recurring theme for Pirates fans: the franchise’s inability to retain talent, both on the field and off of it.