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Born in Marietta in Love County near Ardmore, [[Oklahoma]], to Jack Dillard and former Virgie Fife, Dillard was a veteran of the [[United States Army]]. He first worked as an assistant county agent in Gregg County, Texas, which encompasses the city of Longview. But on Thanksgiving Day in 1959 he switched his focus to become the farm director for KWKH radio in [[Shreveport]] even though he had never been on radio at that time. He also wrote a weekly farm column for ''The Shreveport Times.'' Dillard also became an auctioneer, and co-owned Double D Auctions, which was established in 1965 in Waskom, Texas, with his partner James Michael Duncan (born 1939) of Marshall, Texas. In 2002, he became a minority owner of KMHT Radio, still held by the Dillard family. His journalism career spanned a half century.<ref name=obit>Life Story for Jack Bennett Dillard, Sr. | The Cammack Family - Directors of Funerals, accessed May 20, 2025.</ref>

Born in Marietta in Love County near Ardmore, [[Oklahoma]], to Jack Dillard and former Virgie Fife, Dillard was a veteran of the [[United States Army]]. He first worked as an assistant county agent in Gregg County, Texas, which encompasses the city of Longview. But on Thanksgiving Day in 1959 he switched his focus to become the farm director for KWKH radio in [[Shreveport]] even though he had never been on radio at that time. He also wrote a weekly farm column for ''The Shreveport Times.'' Dillard also became an auctioneer, and co-owned Double D Auctions, which was established in 1965 in Waskom, Texas, with his partner James Michael Duncan (born 1939) of Marshall, Texas. In 2002, he became a minority owner of KMHT Radio, still held by the Dillard family. His journalism career spanned a half century.<ref name=obit>Life Story for Jack Bennett Dillard, Sr. | The Cammack Family - Directors of Funerals, accessed May 20, 2025.</ref>

Dillard penned a weekly column for ''The Marshall News Messenger'' in Marshall, Texas, for many years and contributed a twice-daily radio program carried by KMHT and its sister station, KGAS, in Carthage in East Texas. He also had a weekly Texas Farm Bureau Radio segment for many years and was affiliated with the Cattlemen's Association, Texas Farm Bureau, the National Association of Farm Broadcasters, and Farm City Week, an agricultural program that encourages young people to purse farm careers. In 2019, he was named "Waskom Citizen of the Year" in the small community of Waskom, Texas, west of Shreveport. In his early years he was also a rodeo photographer.<ref name=obit/>

Dillard penned a weekly column for ''The Marshall News Messenger'' in Marshall, Texas, for many years and contributed a twice-daily radio program carried by KMHT and its sister station, KGAS, in Carthage in East Texas. He also had a weekly Texas Farm Bureau Radio segment for many years and was affiliated with the Cattlemen's Association, Texas Farm Bureau, the National Association of Farm Broadcasters, and Farm City Week, an agricultural program that encourages young people to pursue farm careers. In 2019, he was named "Waskom Citizen of the Year" in the small community of Waskom, Texas, west of Shreveport. In his early years he was also a rodeo photographer.<ref name=obit/>

Dillard and his wife, the former Burniece Freeman, had three sons and a daughter, Jack Bennett Dillard, Jr., and his wife Dottie, Jerry Brent Dillard and his wife Dawn, James Barry Dillard and his wife Nancy, and Janet Burniece Greer and her husband, Gregg. There are eight surviving grandchildren as well. Dillard was an active member of the First [[Southern Baptist|Baptist]] Church of Waskom. He died in Carthage and is interred at Yates Cemetery in Scottsville, Texas.<ref name=obit/>

Dillard and his wife, the former Burniece Freeman, had three sons and a daughter, Jack Bennett Dillard, Jr., and his wife Dottie, Jerry Brent Dillard and his wife Dawn, James Barry Dillard and his wife Nancy, and Janet Burniece Greer and her husband, Gregg. There are eight surviving grandchildren as well. Dillard was an active member of the First [[Southern Baptist|Baptist]] Church of Waskom. He died in Carthage and is interred at Yates Cemetery in Scottsville, Texas.<ref name=obit/>