The Highest-Paid Athletes of All-Time 1. Michael Jordan Career earnings: $1.85 billion (2017 dollars) Jordan still maintains his longtime endorsement relationships with Gatorade, Hanes, Nike and Upper Deck, but the investment that made him a billionaire was the $175 million fire-sale price he got the Charlotte Bobcats (now the Hornets) for in 2010. Jordan bumped his Hornets stake to 90% in 2013, and the team is now worth $780 million. 2. Tiger Woods (Photo by Mike Ehrmann/Getty Images) Career earnings: $1.7 billion The 14-time major winner has played only 18 official PGA Tour events since the start of 2014 because of injuries (he's missed the cut or withdrawn from half of them). Sponsors still see value in partnering with Woods, with TaylorMade, Bridgestone and Monster Energy the most recent additions to his endorsement portfolio. 3. Arnold Palmer Career earnings: $1.4 billion Palmer died in September 2016, but his estat...