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Gary Drewrey

Assistant Superintendent

With Winters Construction since



I help supervise the subcontractors and make sure the job is progressing as planned. I’ve worked on four projects for Winters so far in Tupelo, Pontotoc and Oxford.


I’m married, and we have four daughters, three are married. The youngest graduated this year from Lafayette High School.


I’m the kind of guy that, when I get home at night, I usually stay outside until dark doing something. I love to pheasant hunt in South Dakota, quail hunt in Texas and crappie fish on the reservoirs.


I’m originally from Oxford. I graduated from Ole Miss with a bachelor’s degree in physical education in 1983 and then earned a master’s degree at Mississippi State before returning to Ole Miss to get a degree in educational leadership.

I’m retired as football coach, athletics director and school administrator from Water Valley High School for 25 years and Lafayette High School for five years. I taught health classes in history and coached football and baseball. So I’m not as familiar with the construction end but I’ve done construction my whole adult life, just not to this scale.I worked part-time as a laborer and carpenter, just depending on what we were doing at the time. I’ve always loved the construction business.


I enjoy life. I enjoy work. I enjoy being around other people. I had nine assistant coaches when I was a head coach, and I enjoyed the camaraderie. I enjoy dealing with different personalities. I’m one of eight children, so dealing with different personalities is not hard for me.

I want, when I die, for my kids to think as much of me as I think of my father. That’s really the only goal I’ve had in life. I want my wife to love me just as much as I love her and I want my kids to do the same.