Answer: It hasn’t happened yet. And the record in the Kentucky Derby isn’t much better; only Princess Turia, the 1956 Oaks champion, has a Kentucky Derby winner to her credit, and that was by disqualification when Forward Pass was moved up after apparent winner Dancer’s Image tested positive for Bute, then illegal under Kentucky racing regulations.
The next trick question is a bit subtler than the first. In 150 years, why haven’t Kentucky Oaks winners had much luck in reproducing themselves in America’s biggest races?
The likeliest answer is simple math. Unlike a Kentucky Derby-winning stallion, who may be represented by over 200 foals in a single year, a Kentucky Oaks winner can have only one. Given that no more than 10 Oaks winners are likely to have 3-year-old foals in a given year—and in most years, it has been less than that—the odds are heavily stacked against them even compared to their Kentucky Derby-winning brethren, who in any given year will have hundreds of foals of the requisite age between them. For 2022, the year in which this year’s Derby and Oaks contenders were born, 17,146 Thoroughbred foals have been registered in the United States. Even if only foals out of stakes-winning or stakes-producing mares are considered, the Oaks winners’ progeny are outnumbered by hundreds if not thousands to one by other foals which at least have some chance of having inherited the genetic wherewithal to be top-level winners.
At this time, eight Kentucky Oaks winners have current 3-year-olds. While a review of these offspring proves nothing in itself, it does serve as a snapshot of the odds against even a well-bred, high-performing mare with excellent breeding opportunities to produce a runner showing high enough class in the spring of its 3-year-old season to make the starting gate on Churchill Downs’ biggest days.
2004 Kentucky Oaks winner Ashado’s 2022 foal is Bernardo, a Bernardini gelding who has placed third twice from 10 starts. He is a full brother to 2018 Runhappy Stakes (USA-L) winner Westwood, Ashado’s only black-type winner from 12 other named foals.
Lemons Forever (2006 Oaks) has an unraced 2022 filly by Speightstown, Forever Speighty. The only Kentucky Oaks winner to be named the Kentucky Broodmare of the Year, Lemons Forever is the dam of 2017 American champion dirt female Forever Unbridled (by Unbridled’s Song) and her Grade 1-winning full sister, Unbridled Forver, who took her top-level win in the 2015 Ballerina Stakes.
Proud Spell (2007 Oaks) was exported to Japan, where her 2022 filly by Duramente, Proud Moment, was foaled; this filly has started once without placing. Proud Spell’s first foal, indian Spell (by Indian Charlie), is her only stakes winner, having captured the 2013 Miss Woodford Stakes at Monmouth.
Plum Pretty (2011 Oaks) is the dam of the 2022 Speightstown filly Pretty Speightful, who has not raced. Plum Pretty has produced only one winner during her broodmare career.
Believe You Can (2012 Oaks) is the dam of Bells of Maranello, a Nyquist filly who is unraced, Believe You Can has previously produced multiple Grade 2 winner Conclude (by Collected) and Grade 3-placed stakes winner Believe in Royalty (by Tapit) from five previous named foals.
Lovely Maria (2015 Oaks) was exported to Japan. Her 2022 foal, the Lord Kanaloa filly Heart Meteor, has raced once without placing. Neither of Lovely Maria’s two previous foals were winners.
Abel Tasman (2017 Oaks) has a 2022 filly by Into Mischief named Take a Look. She is unplaced in two starts, and Abel Tasman has yet to have a winner from three foals of racing age.
Serengeti Empress (2019 Oaks) produced the Into Mischief colt Invictus as her first foal in 2022. He has won one of his two starts.
Rags to Riches (2006 Oaks), Blind Luck (2010 Oaks), Untapable (2014 Oaks), and Cathryn Sophia (2016 Oaks) had no live foal in 2022 although they were still active producers at that time. None of the Oaks winners from 2020-2024 began producing foals until after 2022.
Among this year’s Oaks and Derby contenders, the one with the closest connection to an Oaks winner is Bourbonette Oaks (USA-L) winner Bless the Broken, whose dam is a half sister to 2013 winner Princess of Sylmar. She’s currently listed at 30-1. Take that for what it’s worth, and perhaps next year the stars will come together to bring the son or daughter of an Oaks winner into the spotlight on one of racing’s biggest days.