11. Dan Marino – $36 Million

Former Miami Dolphins quarterback Dan Marino is still considered the best player in franchise history. Dan isn’t broke today but, after earning one of the highest salaries of his time, he did go bankrupt and he stayed broke for almost five years. Marino wasn’t much into wild parties – he lost his fortune by making one horrible investment. Instead of a wide portfolio, he put all of his millions into ‘Digital Domain,’ a virtual-reality developer.

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The company never achieved a successful prototype and Marino lost everything. Any worthwhile financial adviser would warn him not to “put his eggs in one basket”. Of course, after so many NFL players were scammed by wannabe-advisers, it’s no wonder Dan insisted on making his own decisions.