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.
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.
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.
Prenderagst, a trainer noted for his handling of precocious two-year-olds,[2] trained the colt at his stable at the Curragh, County Kildare.
[6] Before the start of the 1952 season, Windy City was taken to the United States and offered for sale by his owner, Ray Bell.
[8] Windy City II, as he was now named, finished unplaced on his American debut, but at the end of January he won the San Gabriel Stakes over seven furlongs at Santa Anita Park, beating A Gleam and Hill Gail.
Ridden by Eddie Arcaro, he started favourite and won by two and a half lengths, with Hill Gail in seventh.
[10] In the Santa Anita Derby over nine furlongs, Windy City II started 1/2 favourite but finished second, beaten four lengths by Hill Gail.
The independent Timeform organisation awarded the colt a rating of 142, the second highest they had given up to that time, behind Tudor Minstrel and equal with Abernant.
[14] Windy City was officially retired in January 1953 and began his career as a breeding stallion at Sunnyslope Farm at Riverside, California.