Generous, the champion three-year-old of 1991, has died at the age of 25.
The Paul Cole-trained colt took his three-year-old campaign by storm winning the Epsom and Irish Derbies along with the King George VI and Queen Elizabeth Stakes.
He stood at Alfred Buller's Scarvagh House Stud in Northern Ireland for over eight years.
"He was unbelievably intelligent for a horse, kind and truly regal," Buller said in a statement.
"He will be sadly missed and, to all involved with him, it has been a privilege to have cared for him and looked after him during his last period of life."
Generous was also a top juvenile, springing a 50-1 surprise in the Dewhurst Stakes at Newmarket in October 1990 before finishing fourth in the 2000 Guineas on his seasonal return.
"He was a special horse. You have never seen a kinder and more likeable animal," Buller said.
"He got fan mail and Christmas cards, even up to this year, and the guy who looked after all his fan mail used to send out wee bits of hair from his tail in a plaque as a souvenir.
"There are other stallions, all of whom were champions in their own way, but there was only one Generous."