Comrie worked briefly as a stockbroker and was formerly a college soccer coach, primarily at Holy Cross.
When he was ten, Comrie's father moved to the U.S. where he settled in Brooklyn and worked to bring over his family.
Soon after, the Comrie family moved to Bedford-Stuyvesant a particularly harsh neighborhood in Brooklyn to join his father.
Comrie attended Fort Hamilton High School where he continued to play soccer.
[2] After high school, Comrie entered the University of Connecticut where he majored in home economics and played on the powerhouse Huskies soccer team from 1979 to 1982.
While Comrie finished his collegiate career in 1982, he did not graduate with a bachelor's degree in fashion design until 1986.
In 1982, the Montreal Manic of the North American Soccer League (NASL) drafted Comrie.
On 19 October 1987, now known as Black Monday, Comrie suffered significant losses, as he found he had not diversified his investments properly, placing large bets on instruments that inevitably collapsed.
At the age of 27, Comrie left his stockbroker career and went to France for a try out where he spent six months playing for Montpellier HSC.
According to the NCAA, Comrie made more than 300 impermissible phone calls to several prospective student-athletes, many before the contact period and others that exceeded weekly limits.
[13][14] On 6 March 2012, Comrie was appointed manager of USL Premier Development League team, Worcester Hydra, for their inaugural season.