Total earnings: $20.5 million Prize money: $8.5 million Endorsements: $12 million Williams regained the No. 1 ranking in the world in February for the sixth time in her decorated career. She has racked up 15 tournament victories since the start of 2011. Her $47 million in career prize money is 65% more than second ranked Venus Williams. Nike, Wilson, Gatorade and OPI have endorsement deals with Williams and she holds equity deals with HSN, Sleep Sheets, Mission and the Miami Dolphins.