Robert Bailey

Super Bowl XXX and XXXV Champion. Former cornerback for the Los Angeles Rams, Dallas Cowboys, Washington Redskins, Detroit Lions and Baltimore Ravens. President of Rosenhaus Sports Representation.

Athletes and entertainers face unique wealth management opportunities, considerations and challenges. The athletes and entertainers we interviewed shared their personal stories and perspectives to highlight the need for more financial education in the sports and entertainment world. We thank them for being strong advocates of financial literacy.

Robert’s advice

“Work with financial advisors who are focused on financial education and helping you and your family gain insights on how to plan for your long-term goals. You should be able to explain how an investment builds or preserves wealth—before you invest your money.”

Family values

Robert was nine years old when his family moved from Barbados to Miami in search of a better life. Although his mother and father worked long hours, they made time for talks around the family dinner table. “My parents stressed the principles of hard work and accomplishment. We were chasing success.” For Robert, the importance of academics was so firmly established that the eventual two-time Super Bowl champion never even considered the NFL until his final year with the University of Miami Hurricanes. “I only thought about going to medical school.”

A wake-up call

With the Hurricanes, Robert earned two national championship rings. The Los Angeles Rams selected him in the 1991 NFL Draft. He soon discovered that managing his NFL earnings was a challenge. “I had no budget in place. By the end of my first year, I had to borrow $10,000 against my second year. I needed the money to make it through the months before training camp.” It was a wake-up call. “I started saving every penny.”


By the end of my first year, I had to borrow $10,000 against my second year. I needed the money to make it through the months before training camp.


In the history books

In 1994, in a game between the Rams and the New Orleans Saints, Robert made history. He scored a touchdown by returning a punt for 103 yards, the longest punt return in NFL history. He was signed by the Dallas Cowboys in 1995. The team won Super Bowl XXX the following year. While enjoying a higher income and more success on the field, Robert also became more interested in investing. “I started asking, ‘Who is making money in this country?’ I learned about stocks and bonds and how to evaluate companies.”

He vowed never to repeat the financial mistakes he made in his first year with the NFL. “I refused to buy jewelry, expensive cars or anything that doesn’t bring value. I look at everything as an investment. If I spend $5,000 on going out each month, that’s $60,000 in a year. I could invest that money instead and receive a healthy return. I started seeing everything in a different perspective.”

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