After a short stint in minor league baseball with the New York Mets, Boston Red Sox, and the Mexican League, Dennis Gilbert rose through the ranks of financial sales to form the nationally acclaimed insurance advisory firm, The Gilbert Group of Beverly Hills, which lists legendary TV Host Larry King among its clients.Gilbert’s accomplishments have far exceeded his humble beginnings in Gardena, California, where, as a child, he honed his work ethic as a newspaper delivery boy and door-to-door salesman in the fifties and sixties.Gilbert found himself at a crossroad when his baseball career ended.
He was scared out of his mind and not sure what to do next. So, he went to work back on the baseball diamond as a coach at Los Angeles City College (LACC). The pay was next to nothing, but he was working.The course of Gilbert’s life changed forever when one day he noticed that the farther of his first baseman drove a Cadillac. Gilbert drove a Dodge Van. Gilbert’s curiosity and ambition prompted him to ask the father about his line of work. The gregarious parent invited Gilbert to lunch and, over a meal, introduced him to the field of insurance sales.Gilbert’s illustrious business career doesn’t end with his preeminent insurance practice. During his time in sports, Dennis was able to develop some important relationships. Included among those were friendships with the Brett brothers, John, Ken, Bobby, and George. They all became insurance clients. 
Fast forward a few years and Gilbert receives a phone call from George, who would go on to be inducted into baseball’s Hall of Fame. George shares with Gilbert that his brother Bobby, who was handling hs finances, is having problems negotiating George’s contract with then-Kansas City Royals owner Ewing Kauffman.George asks Dennis if he will help with the negotiations. Gilbert agrees, starting a new chapter in his professional career as a sports agent. Nicknamed “Go-Go” by former major leaguer Rick Dempsey, Gilbert hustles 7-24 to grow the practice into one of the most powerful sports agencies in the country, negotiating more than 1,000 baseball contracts for Major League stars such as Barry Bonds, Bobby Bonilla, Jose Canseco, Brett Saberhagen and Mike Piazza.
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One of the most fascinating and visionary contracts Gilbert negotiates is for Bonilla in the late 90’s. It is still talked about today, although Bonilla has long been retired. Why? Because the contract still pays Bonilla and will continue to do so through 2035.At the time, the New York Mets owed Bonilla $5.9 million for the 2000 season. They no longer wanted him and desired to use the money to sign other players to immediately compete for a championship. Gilbert reached an agreement with the Mets to defer payment of Bonilla’s salary. The agreement stipulated that the Mets would begin paying Bonilla the deferred salary in yearly installments of $1,193,248.20 through 2035 beginning on July 1, 2011 and that the deferred salary would earn 8-percent interest per year.Thanks to the magic of compound interest, it means the cumulative payout of Bonilla’s contract will come to a whopping total of $29,831,205 or almost 5 times the amount originally owed the former sandlot star. Interestingly, it also means the 55-year-old Bonilla will out earn rising New York Yankees star Aaron Judge this year, as well as many other active baseball players. Judge will earn $622,300. 
This is a wonderful illustration and comparison for all of us, perhaps kids the most, on the difference in value between power hitters and the power of compound interest.Gilbert retired from the sports agent business in 1999. Today, Dennis is still active in insurance, he is a special assistant to Chicago White Sox owner Jerry Reinsdorf, as well as chairman and co-founder of the Professional Baseball Scouts Foundation, a non-profit organization which raises money for ill or financially troubled scouts.
Questions and Answers
Renick: Your love and passion for baseball and people led to your career in insurance, finance and sales. Did those subjects areas come naturally to you?
Gilbert: No. I had to learn and study them. I probably had to study twice as hard.
Renick: What role did reading play in your professional development?
Gilbert. It played a significant role. I read as much as I could. I always like to be improving.
Renick: What is the most important money habit you learned as a child? Please share the story behind how you learned the habit and what impact it has had on you throughout your life.
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Gilbert: We did not have any money. I learned out of necessity that I had to work and work hard. I first earned money as a newspaper delivery boy and then as a door-to-door sales person.
Renick: How important was compound interest to Bobby Bonilla's contract?
Gilbert: It wasn't only that the compound interest was important, it was that it was tax deferred. Compound interest grows much faster when it isn't being taxed. It’s interesting, I’ve negotiated lots of contracts throughout my career, including ones for Barry Bonds, but the Bonilla contract is the one people talk and write about the most.
Renick: What are Dennis Gilbert's Top Five Financial Principles?
Gilbert: There are not five principles. There is only one. It is not what you make that matters most, it's what you keep!