Brian Gay, unfortunately, was heading toward a crossroads. In his late 40s, with more than 600 starts on the PGA Tour and his job becoming more of a grind than a joy, doubts about his future in golf crept into his head. Stay on the PGA Tour or head to the PGA Tour Champions? Then he went to Bermuda. On the first day of November, after missing nine of his last 11 cuts, Gay defeated Wyndham Clark in a playoff to win the Bermuda Championship, his fifth PGA Tour title and first since 2013.