This project is an investigation into the many financial issues professional athletes face. These issues include bad spending habits, poor investments, freeloaders (posses/entourages), and more. Following is an explanation of Financial Planning and Wealth Management, and how the application of these strategies and tactics - specifically the use of Sustainable Withdrawal Rates in a Capital Sufficiency Analysis - can help to avoid such issues. An illustration of these practices "in action" is given through a case study of fictional athletes and portfolios. Lastly, recommendations are given on potential solutions that could help prevent these problems from affecting more athletes.