With 19 postseason appearances, seven President’s Trophies, 601 wins and six league championships during his 26-year tenure, Scott Pickler has created a lasting legacy as manager of the Yarmouth-Dennis Red Sox.

Pickler, often referred to as “Pick,” took his role as manager of Y-D back in 1998 and has become synonymous with the team and the Cape as a whole since then. He has racked up an immeasurable amount of feats, including the most wins by any manager in the history of the Cape League. Along with his time on the Cape, he spent 35 years as the head coach of Cypress College, a community college in California.

The first Cape League championship for Pickler came in 2004, which started a stretch of three championships in the span of four years for the Red Sox (with titles in ‘06 and ‘07). Pickler added three more championships to his tally with a three-peat in ‘14, ‘15 and ‘16. Overall, his six championships and seven President’s Trophies are the most by any Cape League manager.

Picker’s most recent accolade came in 2024 when he added his ninth division title and another President’s Trophy to his storied career with Y-D completing the regular season atop the standings at 24-12-4. He also became the first Cape League manager with 600 wins on Aug. 1, 2024 when the Red Sox defeated the Harwich Mariners 7-4.

During his tenure, Pickler has managed around 125 future Major League Baseball players. Some of the most notable names that he has managed include: 2024 NL Cy Young Award winner Chris Sale, Guardians pitcher Shane Bieber, Giants former catcher/current President of Baseball Operations Buster Posey, Red Sox pitcher Walker Buehler, star reliever David Robertson, World Series champion Justin Turner and numerous others.

Pickler’s legacy goes far beyond what he’s done on the Cape, though, as he won five state championships (‘91, ‘94, ‘97, ‘03, ‘13) during his time as head coach of Cypress. Pickler still serves as Head Coach Emeritus for Cypress, now in his 40th season with the team, and has accumulated more than 1,000 wins and led more than 400 student-athletes to receive scholarships at four-year schools.

Thanks to his time with both Y-D and Cypress, Pickler finds himself as a member of various different Hall of Fames across the country. He was inducted into the Cypress College Athletics Hall of Fame in 2017, along with both the Cape League Hall of Fame and the American Baseball Coaches Association Hall of Fame in 2019. Last year, he was welcomed into the California Community College Baseball Coaches Association Hall of Fame for his success at Cypress.

Off the field, Pickler has been married to his wife, Sharon, for over 40 years and she is present at every game at Red Wilson Field throughout the summer. They also have two children together, Jeff and Kari.

As he enters his 27th season leading the helm for Y-D, Pickler has his sights set on adding even more accolades to his already prestigious career.