As a trainer, he won his first race in 1959 at Florida's Sunshine Park but made his reputation at racetracks in his native Maryland.
In 1987, he won race number 2,500 of his career at Tampa Bay Downs.
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He was a long-time fan favorite at Florida Downs in Oldsmar, Florida where he won four races on a single day on February 15, 1968, set a season record with 75 wins in 1969, and by 1975 had won five riding titles.
In 2007, Hall of Fame trainer Carl Nafzger brought his 3-year-old Street Sense to Oldsmar for the Tampa Bay Derby, and the colt's victory was a springboard to his win in the Kentucky Derby at Churchill Downs.
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Another Hall of Fame trainer, William Mott, selected Tampa Bay Downs for the first 2011 starts for his 3-year-old filly Royal Delta and 4-year-old colt Drosselmeyer.
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Legendary names like Grantland Rice, Red Smith, Fred Russell and Arthur Daley became regular visitors, calling the track the “Santa Anita of the South.”
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The daughter of Chester Howell Ferguson, for whom the University of South Florida’s College of Business Administration building is named, Thayer has been active in thoroughbred racing and has been in ownership with her brother, Howell Ferguson, of Tampa Bay Downs since 1986.