During his time in professional golf, Green has had a reputation for rebelliousness and a propensity to pull stunts. He has had over two dozen fines levied by the PGA Tour for his bad boy antics. Some of his antics included sneaking friends into The Masters in the trunk of his car, drinking beer on the course while playing with Arnold Palmer at the 1997 Masters, and hitting golf balls through narrow openings in sliding-glass doors. Other fines were for more mundane offenses like swearing on the course, criticizing officials, and signing autographs while playing. His personal problems—divorces, gambling, clinical depression—led to near financial ruin, and affected his playing time and the quality of his play. In his 40s, Green had difficulty maintaining his PGA Tour playing privileges and was forced to play some on the Nationwide Tour.