Dennis Gilbert

Dennis Gilbert serves as a Managing Partner at Higginbotham Financial, bringing more than five decades of experience across life insurance, estate planning and sports management. He has consistently ranked among the top one percent of life insurance professionals nationwide.

Dennis began his professional career as a minor league baseball player before transitioning into life insurance, where he has built a distinguished practice serving high-net-worth clients in the entertainment and sports industry. At the same time, from 1979 to 2000, he established himself as one of the most influential sports agents in the country, founding the Beverly Hills Sports Council, which became the top sports agency in the United States during its time.

Over the course of his sports management career, Dennis negotiated more than 1,000 player contracts and played a pivotal role in transforming the salary structure of professional baseball. He represented some of the game’s most iconic players, including Barry Bonds, Rickey Henderson, Mike Piazza and George Brett. He also represented two iconic figures in broadcasting, Vin Scully and Larry King. He is perhaps best known for negotiating the landmark deferred compensation contract for Bobby Bonilla, widely regarded as one of the most creative deals in sports history. Since 2002, he has served as Special Assistant to the Chairman of the Chicago White Sox, advising on player contracts and personnel matters.

Throughout his career, Dennis has earned numerous honors, including “Man of the Year” from the Anti-Defamation League, a Lifetime Achievement Award from the Baseball Assistance Team and induction into the Los Angeles City College Hall of Fame. He has also received “Man of the Year” honors from Equitable, Nationwide and Mutual of New York.

Dennis’s commitment to giving back includes serving as Founder and Chairman of the Professional Baseball Scouts Foundation, which has raised millions for financially vulnerable scouts and their families. He also financed the development of the baseball field at Southwest College and has served on the MLB’s Salary Arbitration and Player Development committees. Most recently, he was named Commissioner of Perfect Game and founded the Believe in Baseball Foundation to support underprivileged players.

Dennis resides in Holmby Hills, California, with his wife, Cindi. He enjoys spending time with their three daughters and grandchildren.