University of Southern California

Dennis J. Gilbert
The Gilbert Group

As The Gilbert Group Senior Partner and co-founder, Dennis Gilbert created The Gilbert Group to serve as the preeminent resource for serving high-net worth individuals and families across sports, entertainment and business. He consistently ranks in the top 1% of life insurance professionals nationwide.

Dennis began his career as a minor league baseball player, after which he pursued a career in life insurance and taught continuing education estate planning to members of the CPA Society in the State of California. These CPAs, who were primarily entertainment business managers, gave Dennis an entree into the Hollywood community through which he acquired an A-list, entertainment industry clientele.

Dennis excelled at developing life insurance policies and creating wealth protection, and he knew these skills could help baseball players achieve better financial success. As his insurance business continued to thrive, he took on an additional career as a sports agent. Within a year, Dennis had developed the free agent system; he ultimately transformed the salary structure of professional baseball forever.

As baseball's leading agent, Dennis set new standards for creating player contracts. He personally negotiated over 1,000 contracts, broke salary barriers and achieved unprecedented contractual success for players such as Jose Canseco, Bobby Bonilla, Barry Bonds, Joe Magrane, Bret Saberhagen, George Brett, Danny Tartabull, Mike Piazza, Brady Anderson, Curt Schilling, Ricky Henderson, Kevin Appier, Scott Erickson, Rod Beck, Trevor Hoffman and many more.

While Dennis focused on insurance and estate planning, the baseball industry continued to seek his counsel. In 2000, the Chicago White Sox recruited him to serve as Special Assistant to Chairman Jerry Reinsdorf. In addition to reviewing contracts and negotiations, Dennis provided key input on personnel and scouting-related matters

Dennis combines his passion for baseball and community as the Co-Founder and Chairman of the Professional Baseball Scouts Foundation (PBSF). Dennis has helped the PBSF raise more than $4,000,000. He also personally financed the building of an inner-city baseball field at Southwest Community College, home to baseball's RBI Youth Program. The ballpark, Dennis Gilbert Field, celebrated its Opening Day on January 20, 2002.

In addition to PBSF, Dennis serves as a member of Cedar Sinai's Board of Governors. He also sits on Major League Baseball's Salary Arbitration and Player Development committees. He has been named "Man of the Year" by the Anti-Defamation League, has been inducted into LA's Jewish Sports Hall of Fame and was the first inductee into the Los Angeles City College's Hall of Fame.

Dennis is a member of the National Association of Insurance and Financial Advisors (NAIFA), and the Advanced Association of Life Underwriters (AALU). Dennis resides in Holmby Hills, CA, with his wife Cindi. Together they have three beautiful daughters.