Jerry Lawless graduated from the University of Toronto with a Bachelor of Arts degree in 1955 and started teaching in Englehart, Ontario. In 1956, Jerry moved back to Cobourg where he began teaching and coaching at C.D.C.I. West. While teaching, Jerry continued his own education by studying at night and during summers to complete a Bachelor of Physical and Health Education degree at McMaster University in 1962. The following year, Jerry was appointed head of the Department of Physical Education.
In those early years, Jerry coached anywhere from five to nine different teams due to a shortage of coaches. On one occasion, Jerry coached the school's soccer and volleyball teams to championship wins on the same day. As a coach and a teacher, Jerry influenced the lives of countless students, helping to develop both their athletic skills and more importantly, imparting to them valuable life lessons.
Jerry would go on to coach numerous teams (volleyball, basketball, soccer) and individuals (particularly in track and field) to championship wins. Some of the most notable teams were 1967 and 1968 Kawartha and COSSA Boys Volleyball as well as 1975, 1978, and 1979 Kawartha and COSSA Midget Boys Basketball. In recognition, Jerry was a recipient of the Pete Beach Award, a provincial coaching excellence award given to outstanding coaches for their contributions to better their sport and athletes.
Upon his retirement in 1988, C.D.C.I. West presented him with the Coach's Dedication Award and named two athletic awards in his honour: the Jerry Lawless Coaching Award and the Jerry Lawless Senior Male Athlete of the Year Award. In 2005, the gymnasium at C.D.C.I. West was christened the Jerry Lawless Gymnasium.
In a 1967 profile in the Cobourg Daily Star, no less an authority than Layton Dodge wrote that “Many years from now, however, C.D.C.I. West graduates will not remember Jerry Lawless for the number of winners he produced, directed, assisted or just encouraged. They'll remember him for the kind of person that he was. And that, I suggest to you, dear reader, is undoubtedly the finest compliment they could ever hope to pay him.”