True to his reputation, he was something of a handful behind the barrier and when the tapes went up Gordon Richards is said to have lost his irons. a medium-sized chestnut, well nigh impossible to fault in conformation, symmetry or balance. The Bloodstock Breeders Review of 1951 report of the Gimcrack by James Park follows.

Ridden by English champion jockey Gordon Richards he started 5/4 favourite and won by five lengths from Pharaos. Later that month, Windy City was moved up in distance to six furlongs for the Gimcrack Stakes at York Racecourse. The colt was back in Ireland in August and took the Phoenix Plate over five furlongs at Phoenix Park Racecourse by eight lengths. He was then sent to England where he won the Oulton Stakes at Chester Racecourse in May by five lengths. Windy City made his racecourse debut at Phoenix Park Racecourse in April, winning a maiden race by ten lengths.

Prenderagst, a trainer noted for his handling of precocious two-year-olds, trained the colt at his stable at the Curragh, County Kildare. He was bought for 700 guineas by Paddy Prendergast on behalf of American owner Ray Bell. Īs a yearling, Windy City was sent to the sales at Dublin where his modest pedigree meant that he attracted little interest. Windy City's dam, a French-bred mare named Staunton, came from a relatively undistinguished Thoroughbred family which had produced little of note since the 1901 Epsom Derby winner, Volodyovski. He was by far the most successful horse sired by Wyndham, a sprinter whose most important wins came as a two-year-old in 1935, when he won the New Stakes at Royal Ascot and the National Breeders' Produce Stakes at Sandown Park. Windy City was a strongly built chestnut horse bred by Herbrand Charles Alexander the son of the 4th Earl of Caledon and the older brother of Field Marshal Alexander. He was retired to stud where he had some success as a breeding stallion. In the following season he was sold and exported to the United States where he twice defeated the future Kentucky Derby winner Hill Gail before his racing career was ended by injury. He was the leading European two-year-old of 1951 when he won four races including the Gimcrack Stakes and was awarded a Timeform rating of 142, which remains one of the highest in the organisation's history. Windy City (also known as Windy City II, 1949–1964) was a British-bred Irish-trained Thoroughbred racehorse and sire. Top-rated two-year-old in Britain, France and Ireland (1951) British-bred Thoroughbred racehorse Windy City

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