While playing golf together, Michael Jordan advised Charles Barkley to restructure his Nike deal — instead of taking $3 million a year in cash, Jordan suggested taking $1 million and converting the remaining $2 million into stock options.
Barkley’s advisors were skeptical of the risk, but he trusted Jordan’s business instincts. Nike was trading at just over $1–2 per share in the early 1990s; it has since climbed to around $62.76 per share. That growth turned Barkley’s bet into a roughly $50 million windfall.
Jordan himself has benefited enormously from Nike — the Jordan Brand recently surpassed $5 billion in annual revenue, and Jordan collects 5% based on his original licensing deal, a payout that now exceeds double his entire NBA career earnings.

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