Down the Rabbit Hole with Jerry Dipoto

Twenty years of playoff drought ended not with a bang, but with a thousand small decisions.

I truly believe that big results come from small, intentional actions. With that in mind, I'm thrilled to introduce a new monthly segment: Down the Rabbit Hole. This series explores the stories and strategies of leaders whose small, deliberate decisions have sparked extraordinary transformations.

For this inaugural feature, I am beyond thrilled to highlight Jerry Dipoto, President of Baseball Operations for the Seattle Mariners.

Jerry embodies the power of purposeful evolution. A former Major League pitcher turned baseball executive, he's transformed the Mariners by embracing a philosophy that small, calculated decisions compound into remarkable outcomes. As President of Baseball Operations, Dipoto has revolutionized how baseball teams approach improvement—not through occasional big splashes, but through consistent, intentional moves that create lasting value. His methodical approach to team building combines analytical insight with a clear vision: every transaction, no matter how minor, should align with long-term organizational goals.

Under his leadership, the Mariners have built one of baseball's most dynamic player development systems and ended a two-decade playoff drought, proving that sustainable success comes from daily commitment to improvement. In both his pitching career and executive role, Dipoto has demonstrated that transformative change happens through deliberate action and unwavering focus on the bigger picture.

Jerry Dipoto: Down the Rabbit Hole

Q1: Chief Rabbit is about small actions creating big change. What's one seemingly minor adjustment you've seen completely reshape a player's career or team's direction?
Jerry Dipoto:
In our business, like in all sports, every career arc, every day, every game, every event within a game is a constant series of small changes. In many cases, the changes are physical; simple things like altering hand position as a hitter, as happened with one of our outfielders (Victor Robles) after we acquired him from the Nationals last summer. In his case, the change was profound and led to career-best performance during the season's second half and established him as a key part of our plans moving forward. In other instances, the changes may be strategic, such as a pitcher choosing to prioritize a specific pitch type. Most often, the adjustments are in mental approach or mindset. To me, the mental approach serves as the great separator among successful people in any walk of life.

Most often, the adjustments are in mental approach or mindset. To me, the mental approach serves as the great separator among successful people in any walk of life.

Q2: Throughout your career, what's one unconventional idea or strategy that initially raised eyebrows but ultimately proved game-changing?
Jerry Dipoto:
I retired as a player prior to the 2001 season and immediately moved to the front office, quickly gravitating towards scouting. I didn't realize it at that time, but the first decade of the 2000s was such a unique time in the evolution of the game, with so much experimentation and innovation. Initially, it was smaller-market teams who led the charge, but ultimately the era of information/data management and decision-making became the norm around the league. In the time since, the age of advanced analytics has changed so much about the game, as well as virtually everything else in our everyday lives.

Q3: You're known for making bold moves with the Mariners. How has your approach to making changes evolved since your early days in baseball operations?
Jerry Dipoto:
I have had the privilege of working for five different organizations since retiring as a player 25 years ago. I'm fortunate enough to have a World Series Ring (2004 Red Sox), been with half a dozen playoff clubs in BOS, ARI, LAA, and SEA, have worked with incredible players, and learned from many wonderful teachers along the way. By the time I arrived in Seattle in the fall of 2015, I had developed a clear vision for what I hoped to accomplish. At that time, we had a talented but older core, very limited roster depth, a top-heavy payroll, and a shallow farm system. I thought we had 2–3 years to make a run for the postseason with that core, while simultaneously working in the background to develop the types of systems and programs that would provide a strong foundation for an organizational rebuild.

The result was a dizzying number of transactions geared towards improving the depth around that core. In hindsight, while we failed to reach the playoffs during those first three seasons, we did field fun teams to watch, while also affording ourselves the time to construct the type of infrastructure required of teams who aspire to contend year in and year out. After the 2018 season, we pushed forward with our rebuild, and two years later we emerged with a young MLB roster, one of the top farm systems in the industry, and a network of people, systems, and programs that we believe in. While we remain active in making moves, the pace has slowed considerably, and we now rely on all the work we did to create our organizational model.

Q4: The baseball season is incredibly demanding. What are your go-to practices or routines that help you stay energized and maintain clarity during the grinding schedule?
Jerry Dipoto:
Over the years, I have developed a daily routine that works for me. When I first started in the front office, I took pride in working longer hours and being more places than anyone. Now I prioritize sleep and recovery! My morning routine includes a series of cognitive exercises and games that I go through first thing (with my morning coffee) to wake up my mind, then make sure to move for at least an hour (resistance training, cardio, etc.) before heading to the office/ballpark. I'm always reading something not related to baseball, which provides a release, and I love to cook, which requires focus (at least for me!).

Q5: What's a fascinating rabbit hole you've gone down lately that has nothing to do with baseball?
Jerry Dipoto:
Which hole? I'm curious by nature and guilty of getting lost in whatever hole I find 😀 

Closing Thoughts

Jerry Dipoto's journey from pitcher to baseball executive illuminates a profound truth about organizational transformation: breakthrough success rarely comes from singular, dramatic moves, but rather through the patient accumulation of purposeful decisions. His evolution mirrors the very organization he's built—one that values both analytical precision and human development, infrastructure and adaptability, short-term execution and long-term vision.

Breakthrough success rarely comes from singular, dramatic moves, but rather through the patient accumulation of purposeful decisions.

What makes Dipoto's approach particularly compelling is how it extends beyond baseball operations. His personal shift from valuing sheer work volume to emphasizing recovery and mental clarity reflects a deeper understanding that sustainable excellence requires both strategic action and thoughtful restraint. Whether it's adjusting a player's hand position, rebuilding farm systems, or restructuring his own daily routines, Dipoto demonstrates that transformative change happens at the intersection of systematic thinking and willingness to evolve.

The Mariners' journey from a two-decade playoff drought to a revitalized organization with one of baseball's top development systems stands as testament to this philosophy: when every decision, however small, aligns with a clear organizational vision, the compound effect can be extraordinary.

In both baseball and business, the box score may only show the final result, but as Dipoto demonstrates, it's the thousand invisible decisions—made with purpose, patience, and unwavering vision—that truly change the game.

Fans can gain deeper insight into Jerry's baseball philosophy through his regular appearances on the "Mariners Hot Stove" show during the offseason and his candid interviews on the "Baseball America" podcast, where he discusses everything from player development strategies to the future of baseball analytics.

To stay connected with the Mariners' latest moves and Jerry's ongoing transformation of the organization, follow the team on Twitter @Mariners or visit MLB.com/mariners for coverage and updates.

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