Greg grew up in Southern Oregon and graduated from Crater High School in 1976. His fire service journey began in 1974 when he joined the City of Central Point Fire Department as a volunteer firefighter. In 1977, he transitioned into a full-time role with the same department as a paid firefighter.

In 1981, Greg was appointed as a Captain with the Rogue River Fire District, where he demonstrated strong leadership and commitment. His dedication earned him a promotion to Fire Chief in 1987—a role he honorably served in until 2005.

That same year, he joined Fire District 3 as a Battalion Chief, where he continued to contribute his expertise until his retirement in 2015. However, his passion for public service brought him out of retirement in 2018 when he accepted the position of Fire Chief for Jackson County Fire District 4.

Outside of his professional life, Chief Winfrey enjoys spending time in the great outdoors of Oregon—camping, fishing, and enjoying nature alongside his wife Paige, their children, and grandchildren.