A graduate of the University of Kentucky by way of the GI Bill, Ramsey was a trucking industry executive before turning to real estate in the 1970s and then to cellular telephone network franchising in the 1980s primarily along Interstate 75 in northeastern Georgia and southeastern Kentucky. He sold the cellular business, valued at $39 million, in 1994 and bought historic Almahurst Farm near Lexington, renaming it Ramsey Farm.
During his real estate heyday in the 1970s, he developed his passion for horse racing by attending Keeneland, Churchill Downs, River Downs or any track that was open. He first entered racing in 1969 by claiming Red Redeemer for $1,500 at the now-closed Miles Park in Louisville; the horse was blind in one eye and never won again.
Have been the dominant owners in the win category at Kentucky tracks for the past decade including taking the 2010 Churchill Downs fall meeting title, he earned their first title outside the state in 2004, taking honors at Gulfstream, and followed with the Saratoga title in 2008. The Ramseys earned their first Breeders' Cup trophy on their 11th attempt when Furthest Land, a former claimer, won the G1 Breeders' Cup Dirt Mile in 2009.
After a year that saw them win 17 graded stakes, including three Grade 1s in 3 hours on Aug. 17, in 2013 for over $12.2 million in earnings, the Ramseys were named both the 2013 Outstanding Owner and Breeder at the end of the year.
In 2014, the Ramseys started off the year by winning both the Spiral Stakes and Louisiana Derby with We Miss Artie and Vicar's In Trouble, respectively to have two horses locked into the Kentucky Derby starting gate.