14. Davis Love III, $44,909,170
A two-time Ryder Cup captain, who joined the PGA Tour in 1986, has 21 wins on Tour, including the 2015 Wyndham Championship when, at age 51, he made history by becoming the third oldest player to win a PGA Tour event. A Hall of Famer, Love has one major championship – the 1997 PGA Championship. He finished seventh in the 2019 Sony Open.