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In 1972, he married actress Jo Ann Pflug and they divorced in 1980. Chad was killed in a motorcycle accident in January 1986. Woolery and his first wife, Margaret Hayes, had two children together: Katherine and Chad.

Woolery has been married four times, and has at least five children. Woolery is a Christian who volunteers in ministry. Woolery's contract was not renewed and his final episode aired on December 25, 1981. Griffin offered Woolery $400,000 a year, and NBC offered to pay the additional $100,000, but after Griffin threatened to move the program to CBS, NBC withdrew the offer. In 1981, he was involved in a salary dispute with the program's producers he said in a 2007 interview that he demanded a raise from $65,000 a year to about $500,000 a year because the program was drawing a 44 share at the time, and other hosts were making that much. On January 6, 1975, he began hosting Wheel of Fortune at the suggestion of creator Merv Griffin, who had seen Woolery sing on The Tonight Show. Starting as a singer, Woolery appeared on an episode of Your Hit Parade.

During that time, he made his first game show appearance on an episode of Tattletales, alongside then-wife Jo Ann Pflug. Dingle on the children's television series New Zoo Revue in the early 1970s.

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