Brian Cashman Speaking Fee: $100,000 to $125,000

Brian Cashman, born on July 3, 1967, in Rockville Centre, New York, has been a pivotal figure in Major League Baseball for over three decades. Raised in Washingtonville, New York, he developed an early passion for baseball, attending a summer camp hosted by Bucky Dent before high school. His enthusiasm for the sport was further fueled when he served as a batboy for the Los Angeles Dodgers during spring training in 1982, thanks to a family connection with former Dodger Ralph Branca. Cashman played college baseball at The Catholic University of America, where he was a four-year starter at second base and set a school record for most hits in a season. He graduated in 1989 with a bachelor's degree in history. In 1986, while still in college, Cashman began his career with the New York Yankees as an intern. His dedication and work ethic led to a series of promotions: assistant farm director in 1990, major league administrator in 1991, and assistant general manager in 1992. In 1998, at the age of 30, he was named senior vice president and general manager of the Yankees, becoming the second-youngest GM in MLB history. Under his leadership, the Yankees won the World Series in his first three seasons (1998–2000), a feat unmatched by any other GM. Cashman's tenure has been marked by a commitment to both tradition and innovation. He has balanced the Yankees' storied legacy with modern strategies, emphasizing player development and analytics. His approach has led to multiple division titles, American League pennants, and a World Series championship in 2009. Despite the challenges of maintaining a competitive team in a high-pressure market, Cashman's adaptability and strategic acumen have kept the Yankees consistently in contention. Beyond his executive role, Cashman is known for his candid communication style and sense of humor, traits that have helped him navigate the complexities of baseball management. He has also engaged in philanthropic efforts, such as participating in events to raise awareness for the Wounded Warrior Project and homelessness. His leadership extends beyond the baseball diamond, offering insights into effective team building and organizational success. As of 2025, Cashman continues to serve as the Yankees' general manager, a position he has held for over 25 years. His enduring presence and influence in the organization underscore his integral role in shaping the team's direction and sustaining its competitive edge in the ever-evolving landscape of Major League Baseball.