Rocco became captivated by golf in high school after years of baseball. While at Florida Southern College he began constructing his swing with help from Champions Tour member Jim Ferree and his college coach Charlie Matlock. He started using a long putter to compensate for back problems and in 1991 and when he captured the Doral-Ryder Open he became the first player to win on the PGA Tour using a long putter. He has five career PGA Tour victories. In 2007, Rocco spent the early season as a walking commentator for The Golf Channel. He finished second at the Arnold Palmer Invitational in March of 2007. In 2008, Rocco delighted the golf world with his runner-up finish at the U.S. Open at Torrey Pines. He played Tiger Woods evenly in an 18-hole Monday playoff before finally falling on the first sudden-death playoff hole. It was his best career finish in a major championship. An avid poker player since he began in 2004, Rocco finished 600th out of 5,619 players in his first appearance at the 2005 World Series of Poker's Main Event.