Cowan has caddied for Ed Sabo (1976–1978), Peter Jacobsen (1978–1996), Tiger Woods (1996–1999), Jim Furyk (1999–2024)[1] and Pan Cheng-tsung (2024–present).
"[3] Although he worked with Jacobsen for over 18 years, Cowan's public profile reached its peak while partnered with emerging superstar Woods as his first PGA Tour caddie.
Following the Nissan Open in Los Angeles in February 1999,[4] Cowan was released by Woods in early March for undisclosed reasons,[5] replaced by Steve Williams of New Zealand.
[8] Born in Winslow, Maine, Cowan was a multi-sport athlete at Lawrence High School in Fairfield and graduated in 1966,[9][10] then attended William Penn College in Oskaloosa, Iowa, and played for its golf team.
[12] Cowan is an avowed "Deadhead" (ardent fan of the American rock and roll band The Grateful Dead),[13] and is a member of Congressional Country Club in Bethesda, Maryland, and resides in nearby Rockville with his wife Jennifer and their daughter, Bobbie.