Skip to Content

Our Team

Dennis J. Gilbert | Paradigm Gilbert

Dennis J. Gilbert

Dennis J. Gilbert is one the Managing Principals of Paradigm Gilbert and has served high net worth individuals and families across sports, entertainment and business for over four decades. He consistently ranks in the top 1 percent 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 him 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 and started the Beverly Hills Sports Council Agency. It didn’t take long to become baseball’s top agent, ultimately transforming 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 George Brett, Jose Canseco, Bobby Bonilla, Barry Bonds, Joe Magrane, Danny Tartabull, Mike Piazza, Brady Anderson, Curt Schilling, Ricky Henderson and Trevor Hoffman, just to name a few. In 1999, Dennis sold his interest in Beverly Hills Sports Council

Dennis continued selling large policies to a roster of elite clients. In 2009, he formed The Gilbert Group, another of the country’s top insurance firms. He continues to teach educational workshops to high-end financial, legal and accounting organizations

While Dennis focused on insurance and estate planning, the baseball industry continued to seek his counsel. In 2001, he joined the Chicago White Sox as Special Assistant to Chairman Jerry Reinsdorf. He continues to hold this title today and assist the White Sox in various business matters, such as negotiating and reviewing player contracts, as well as providing 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), an organization devoted to helping scouts and their families who have fallen on hard times. He has helped the PBSF raise more than $1 million and also spearheaded the building of an inner-city baseball field at Southwest Community College, home to baseball’s RBI Youth Program. Dennis was raised in Gardena, Los Angeles, so there is a connection with him and his community. He hopes to provide more opportunity for kids

In addition to PBSF, Dennis 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, received the “Life Time Achievement Award” by Gardena High School’s 50th reunion, inducted into LA’s Jewish Sports Hall of Fame and was the first inductee into the Los Angeles City College’s Hall of Fame. He is a member of the National Association of Insurance and Financial Advisors (NAIFA) and the Advanced Association of Life Underwriters (AALU)

Dennis is truly a passionate man whose storied career continues in entertainment, baseball, insurance and helping those in need. He and his wife, Cindi, reside in Holmby Hills, CA and have three daughters, Ashlee, Shannon and Hailey