Bob Gay graduated from Bishop Feehan High School in 1970 and from Bridgewater State University in 1974 with a B.A. degree in History. Bob was the captain of both his high school and college golf teams. He earned his M.Ed degree in Guidance in 1975. Bob was hired to teach history at Whitman-Hanson Regional High School (W-H) part-time in 1974 and full-time in 1975. He married his college sweetheart, Linda, on July 17, 1977. Their daughter Kristin was born on April 8, 1980 and their son Kevin was born on April 16, 1983. Bob was the coach of the girls' golf team from 1975-79. History department colleague Ron Brown often accompanied Bob with the golf team and played courses such as the Country Club in Brookline and Hatherly Country Club in Scituate. Ron had begun a wrestling team at W-H during the 1977-78 school year. Entering the 1979-80 wrestling season, Ron needed an assistant coach. On Friday evening, November 30, 1979, Ron telephoned Bob and asked him to be his assistant wrestling coach. Bob had never wrestled, but agreed to go to practice the next morning. This was the beginning of Bob's career as a high school wrestling coach. Bob served as Ron's assistant coach from 1979-84. He did not coach during the 1984-85 season as he was completing his M.B.A. degree at UMass Dartmouth.

Ron Brown left W-H to teach at B.C. High, where he would also begin a wrestling program. Bob agreed to coach a young and inexperienced W-H team for the 1985-86 season. Bob focused on physical conditioning and the team responded with a league championship despite only having two returning varsity wrestlers. In February 1988, W-H won its first South Sectional championship, with Bob being named Coach of the Year. W-H won a second league championship over Division 1 power house Randolph on February 14, 1989 before a standing-room only crowd. Many area coaches and officials were in the W-H stands watching this epic match. Previously, on December 23, 1987, Bob had been appointed assistant principal at W-H, while continuing to coach. The mid-1990's saw W-H as one of the top teams in Massachusetts setting a state record of winning 53 consecutive dual meets over three seasons. W-H won South Sectional Championships in 1994 and 1995, along with Bob being selected as Coach of the Year. He was also the Division 2 Boston Globe Coach of the Year in 1994. On July 1, 1995, Bob was named principal of W-H. In January 1997, he had his 200th win at Wayland High School. In his 16 years as the W-H varsity coach, his team record was 271-60-2. Bob's teams won 9 league championships, 3 sectional championships, 9 individual state champion wrestlers, and more than 30 sectional champions.

Also, in the 1990's Bob worked with Chelmsford coach Bruce Rich to realign wrestling from two divisions to three. They believed that smaller schools such as Cohasset could not compete consistently with the larger Division 2 schools. The MIAA approved Bob and Bruce's plan and three wrestling divisions still continue to this day. Bob left W-H to become principal of North Attleboro High School (NA) on July 1, 2001. Although he would not coach again for a dozen years, Bob served as the MIAA Division 2 tournament director during that time. He also worked as an announcer for North TV, covering NA wrestling. In 2005, Bob was named Met Life Massachusetts High School Principal of the Year.

Bob retired from the public school system on June 30, 2010 and started the very next day as principal of Coyle & Cassidy (CC) High School. In 2012, Bob was selected to the Massachusetts Wrestling Coaches' Hall of Fame and to the New England Wrestling Coaches Hall of Fame in 2016. As principal of CC, Bob was asked to coach a cooperative wrestling team with Bristol-Plymouth (BP) Regional Technical School. He was a volunteer assistant in 2012-13 and became varsity coach in 2013-14. Bob won his 300th dual meet on December 30, 2015. The BPCC team won its first league championship in school history in 2017. In the past 5 years, BPCC has had several Sectional champions, more than 30 league all-stars, more than 20 state qualifiers and 10 state place finishers. Bob was voted Mayflower League Coach of the Year in 2017 and the Taunton Gazette Coach of the Year in both 2016 and 2017. BPCC placed 10th at the 2018 Division 3 State Wrestling Tournament. The BPCC team has won 41 dual meets the past two wrestling seasons. Bob's lifetime record is 355-113-4.

Bob gives much credit to the outstanding coaches he has worked with: Paul Holmes, Gary Rabinovitz, Kevin Broderick, Dale Smith, Dave Armstrong, Nick Flynn, and Kyle Hargreaves.

Finally, Bob saves the best for last. He thanks his best friend, soul mate, and wife, Linda for all of her support throughout the years. Bob also thanks his children Kristin and Kevin for their understanding as to why Dad was seldom home in the winter months from 1979-2001.