“The Smartest Thing I Did”: Tracy McGrady’s Financial Lesson Every Athlete Should Learn | Jimmy Bisharat
- Jimmy Bisharat
- 2 days ago
- 5 min read
By Jimmy Bisharat
“I ball like Tracy McGrady.”
There is a reason his name became a lyric. Tracy McGrady was one of the most gifted scorers of his generation, earned hundreds of millions of dollars during his career and eventually became a Hall of Famer. But one of the smartest decisions T-Mac made had nothing to do with basketball. Early in his career, McGrady admitted he did not know much about the business and financial world he had suddenly entered. Rather than pretending otherwise, he surrounded himself with professionals he trusted. Then he took it one step further.
McGrady has said that one of the smartest things he did in his career was hire a third-party auditor who was completely separate from his investment team and financial advisors. That person’s job was not to replace his existing team. It was to independently review the books, understand what everyone was doing and create another layer of accountability. That distinction is important. Trusting your team is important. Having checks and balances is prudent. McGrady understood that you can trust the people around you while still verifying that everything is working the way it should.
That same principle applies to athletes today. You are not expected to become an expert in investing, taxes, insurance, estate planning and every business opportunity that comes your way. Your job is to build the right team, understand the big picture and make sure someone is asking the right questions. An independent financial second opinion could uncover an investment that does not make sense, unnecessary risk, poor tax planning, too much cash, too little liquidity, inadequate insurance or a hole in the financial plan that nobody has addressed. It could also uncover something far worse. But there is another possible outcome that athletes sometimes overlook: the review could confirm that everything is being handled correctly. There is real value in hearing from an independent fiduciary that your current team is doing a great job and that you are on the right track. A second opinion does not always need to create change. Sometimes it creates confidence.
McGrady also showed discipline in how he handled his money early in his career. The Washington Post reported that he kept relatively limited access to his wealth and maintained a modest checking balance compared with what he was earning. The principle is something I discuss with athletes today: separate your wealth from your spending money. A large NIL payment or professional contract should not suddenly become one giant checking account. Taxes, emergency reserves, investments and long-term goals can be funded first, while a defined amount is available for lifestyle spending. In simple terms, pay your future self first and live off the rest. You should absolutely be able to enjoy the money you worked so hard to earn, but your lifestyle should fit within your financial plan, rather than becoming the financial plan.
McGrady has also been transparent about making investment mistakes and becoming more selective over time. That may be one of the most relevant lessons for modern athletes. The more successful you become, the more opportunities tend to find you. Friends have businesses. Someone knows about a real estate deal. A startup needs an investor. A new restaurant is raising money. There is always another opportunity. For a high-earning athlete, “Can I afford this?” is usually the wrong question. “Is this actually a good investment?” is much more important. Who is involved? How does it fit with everything else you own? How much could you realistically lose? Is the potential return worth the risk? And perhaps most importantly, has someone who does not financially benefit from your decision independently reviewed it?
McGrady has talked publicly about seeing players make hundreds of millions of dollars and later struggle financially, including former players asking him for loans or looking to sell championship rings. It is a reminder that making money and building wealth are two very different skills. The part of McGrady's story that stands out to me is not that he made every financial decision perfectly. He didn't. It is that he was willing to acknowledge what he did not know, hire people who did, and then create accountability around those people. That is a financial structure more young athletes should consider following.
If you are earning meaningful money through NIL or a professional contract, a financial second opinion can be one of the simplest ways to pressure-test what you already have in place. As a fiduciary financial advisor working with athletes, my goal is not to assume your current team is doing something wrong. It is to independently look at the full picture and help determine whether anything is being missed. Maybe we uncover a mistake. Maybe we find an opportunity. Maybe there is a hole that needs to be filled. Or maybe I review everything and tell you that you are already in great shape. Either way, you leave with more clarity and confidence about the money you worked so hard to earn.
If you are an athlete, parent or representative who wants an independent second opinion on an existing financial plan, investment portfolio or overall financial setup, feel free to reach out.
Sources:
Gerber Kawasaki Wealth & Investment Management is an investment advisor located in California. Gerber Kawasaki Wealth & Investment Management is registered with the Securities and Exchange Commission (SEC). Registration of an investment advisor does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the Commission. Gerber Kawasaki only transacts business in states in which it is properly registered or is excluded or exempted from registration. A copy of Gerber Kawasaki Wealth & Investment Management 's current written disclosure brochure filed with the SEC which discusses, among other things, Gerber Kawasaki Wealth & Investment Management's business practices, services and fees, is available through the SEC's website at: http://www.adviserinfo.sec.gov .
Jimmy Bisharat is a Financial Advisor of Santa Monica, California-based Gerber Kawasaki Inc., an SEC-registered investment firm with approximately ~$4.78B billion in assets under management and assets under advisement as of 06/30/26. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. This material is for general information only and is not intended to provide specific tax or investment advice. Consult your tax professional regarding your individual situation.To determine which course of action may be appropriate for you, consult your financial advisor. No strategy assures success or protects against loss. Readers shouldn't buy any investment without doing their research to determine if the investments are suitable for their situation. “All investments involve risk and one should consult a financial advisor before making any investments. Past performance is not indicative of future results."
