Bob Gebhard's journey in professional baseball began when he was drafted by the Minnesota Twins in 1965. Although he initially played as a pitcher, his career in Major League Baseball (MLB) was relatively brief. Gebhard made his MLB debut with the Twins in 1971, appearing in a handful of games over two seasons. His time on the mound was limited, and he spent much of his playing career in the minor leagues, where he honed his skills and gained valuable experience.

After retiring as a player, Gebhard transitioned into a front-office role, where he found a new avenue to contribute to the sport. He joined the New York Yankees organization as a scout and later moved to the Montreal Expos, where he served as the Director of Minor League Operations. His work with the Expos laid the foundation for his future endeavors in baseball management.

In 1991, Gebhard took on a new challenge as the first general manager of the Colorado Rockies, an expansion team entering the National League. His task was to build a competitive team from scratch, a formidable undertaking that required strategic planning and a keen eye for talent. Under his leadership, the Rockies quickly became competitive, reaching the postseason in just their third year of existence in 1995. This achievement was a testament to Gebhard's ability to assemble a team capable of competing at the highest level.

Gebhard's tenure with the Rockies lasted until 1999, during which he played a crucial role in establishing the team's identity and laying the groundwork for its future success. His efforts in building the Rockies from the ground up were recognized throughout the baseball community, and he remained a respected figure in the sport even after his departure from the team.