Each year that the Oaks is run, it brings with it different stories and contexts. And if we have a “filly favourite” running, we learn their stories by heart. Some of these narratives stay with us. Join me as I re-memory the fillies and the Oaks runs over the last sixteen years that remain my favourites to this day.
A Brief History of the Kentucky Oaks
Despite the fact that the history of the Kentucky Oaks is as venerable as its twin, the Kentucky Derby, through much of the latter part of the last century it has been treated as the “second” on the card. Yet it’s fair to say that any filly who runs in the Oaks is as exceptional, in every way, as the colts who will run in the Derby on the first Saturday in May. Like the boys, these fillies are the best of their year and, in some Oaks years, even better than the colts that win the Derby.
The first Kentucky Oaks was run in 1875 and won by a filly named Vinaigrette. Its founder was Colonel Meriwether (aka “Lutie”) Lewis Clark, Jr., the grandson of explorer General William Clark, of Lewis and Clark fame. The tempestuous Lutie — who would commit suicide after the stock market crash of 1893 — did much to introduce horse racing to America, also founding the Kentucky Derby and the Louisville Jockey Club, as well as supervising the building of Churchill Downs on land purchased by his mother’s family, the Churchills, after which the track takes its name. In Lutie’s eyes the Oaks and Derby would showcase America’s finest thoroughbreds, just as the Epsom Derby and Oaks did in the United Kingdom.
It was a place built to welcome dreams. And it did just that.
My Favourites: Kentucky Oaks 1990 – 2016
These are the Oaks that most moved me over the last quarter of a century. I have never had much interest in comparing the winners, since each filly ran in different contexts unique to her time and circumstance. But there are two qualities the fillies showcased here share: the racing heart that got them to Churchill Downs in the first place, and the courage to take on their peers no matter the challenge.
1990: SEASIDE ATTRACTION (Seattle Slew ex Kamar, by Key To The Mint)
She was a daughter of Seattle Slew out of a Key To The Mint mare, Kamar, but she was decidedly unlucky to be born in the same year as the incomparable Go For Wand. An over one million dollar Keeneland purchase by William T. Young of Overbrook Farm, Seaside Attraction was trained by D. Wayne Lukas. In the 1990 Oaks, Seaside Attraction would have her work cut out for her: even the legendary Joe Hirsch (in video below) felt the winner was a foregone conclusion. The track was sloppy, but few felt this would hinder Go For Wand, a “filly for the ages.”
(Note: The videotape runs for 41 minutes, but I started it closer to the actual race itself, even though the whole telecast is a treat to watch.)
Hearts were broken on this day, mine among them.
I wanted to see Go For Wand wear the blanket of pink, but her previous start had almost been a walkover, the Churchill track was tiring, and the sheer number of times she had raced as a three year-old may have, indeed, been her Achilles heel. But this takes nothing away from Seaside Attraction, who ran her heart out. And even through my disappointment, I was reminded of the hopefulness that fills the heart in a race of this calibre. It’s the “secret ingredient” of the sport: the knowledge that nothing is certain once the starting gates fly open.
1994: SARDULA (Storm Cat ex Honor An Offer, by Hoist The Flag)
In 1994, Sardula was Jerry and Ann Moss’ Kentucky Oaks filly. The daughter of Storm Cat, like her grandam Terlingua, had been a hot-blooded two year-old and trainer Brian Mayberry had invested hours and hours into teaching her how to relax. This is another “secret ingredient” of racing: colts and fillies that don’t relax when they run are unlikely to do their best work. Too, the risk of injury is far greater when a thoroughbred is wound up too tight.
A year earlier, at Del Mar, Sardula broke into racing with a 10-length victory. A month after that, she won the Del Mar Debutante by 7 1/2 lengths. In April, after a layoff of almost four months, she won the Santa Paula Stakes at Santa Anita by 8 1/2 lengths. And only a month before the Oaks, at Hollywood Park, Sardula won the Princess by 5 1/2. All very Terlingua-like. Sardula was a speedball and she came into the Oaks a multiple-stakes winner. Regular jockey Eddie Delahoussaye would again be in the irons.
But despite earnings of over $800,000, Sardula didn’t start as the Oaks favourite. That honour went to another outstanding filly: Lakeway.
I was, of course, in Sardula’s camp and principally because of my lifelong love for Terlingua. But Sardula’s courage in battling Lakeway to the wire is something I will never forget. It is the mark of a champion and was to be Sardula’s final legacy. Later that year, the filly was diagnosed with osteomyelitis, a painful bone disease. Despite the efforts of veterinary facilities in Kentucky and California, the magnificent Sardula could not be saved. She is buried in California, on the grounds of the veterinary facility where she was humanely euthanized.
1999: SILVERBULLETDAY (Silver Deputy ex. Rockeby Rose by Tom Rolfe
Like so many Oaks contenders, Silverbulletday had a spectacular fan following before she even stepped onto the track at Churchill Downs. Under Bob Baffert’s guidance and in the skilled hands of Gary Stevens, Silverbulletday had won top honours as the Two Year-old Eclipse Champion filly in 1998. As a juvenile, she had raced on the East and West coasts but seemed to prefer the former to the latter, resulting in her being permanently moved to Churchill Downs. There, she reeled off another three straight wins including the G2 Alcibiades and the Breeders Cup Juvenile Fillies.
Silverbulletday’s three year-old campaign was as brilliant as her accomplishments at two. She annexed the Ashland, Black-Eyed Susan, Monmouth BC and Fair Grounds Oaks, the Gazelle, Alabama and Davona Dale Stakes, losing out to Beautiful Pleasure in the Beldame. Her achievement resulted in an Eclipse Award that year. She raced at four but was less accomplished, retiring at the end of the season with over three million USD in earnings. In 2009, she was inducted into the Racing Hall of Fame.
Silverbulletday was a hard-working filly and an honest one. Those who loved her during her racing years loved everything about her, but it was her honesty that won my heart. She always gave everything she had and that determination was breathtaking to witness.
2004: ASHADO (Saint Ballado ex. Goulash, by Mari’s Book)
Ashado: I loved her name and everything about her. She was the first filly in the twenty-first century that I thought of as “My Girl.”
Ashado didn’t win every race at two, running against some powerful competition in Society Selection and Halfbridled, winner of the 2004 BC Juvenile Fillies. But she never gave up either, even though Todd Pletcher cited “morning laziness” ( the filly was so resistant that trainer Pletcher felt guilty working her at all) and the fact that Ashado got bored on the lead as probable causes for the races she lost. Context in the year a thoroughbred races has a direct impact on how they do. And in 2004, Ashado went up against the likes of Storm Flag Flying, Nebraska Tornado, Madcap Escapade and Stellar Jane. But her wins in the Oaks and BC Distaff that year were gutsy and brilliant, earning her Eclipse Champion Three Year-Old honours.
Ashado raced on at four, winning three G1’s, before her retirement in 2005. In 2014, “My Girl” was inducted into the Racing Hall of Fame.
2007: RAGS TO RICHES (A.P. Indy ex. Better Than Honour, by Deputy Minister)
How could you ignore Rags? Although arguably not the most cuddly of personalities, Rags To Riches’ courage — some might say “sheer bloody mindedness” — swept all before her, even the mighty Curlin, whom she defeated in the 2007 Belmont Stakes, despite bobbling at the gate. Everything about this filly was bigger than life, from her size to her stride to her determination to win. Those devoted to A.P. Indy saw in this burly, chestnut daughter a fitting testimonial to an outstanding sire nearing the end of his stud career. And, of course, she was all that, defeating the 2006 Eclipse Champion Two Year-Old and BC Juvenile Fillies winner, Dreaming of Anna, in the Kentucky Oaks.
Rags’ defeat of Curlin and Hard Spun in the Belmont Stakes just a few weeks later was a heart-pounding, gut-wrenching battle to the wire that few will ever forget. It was the first time that a filly had won the gruelling classic in over a hundred years.
Following a number of minor injuries, Rags To Riches was retired in 2008 with in excess of one million USD in earnings.
Rags never gave me that “warm and fuzzy” feeling. I didn’t dream of meeting her, or of giving her peppermints as I stroked her head. But she was greatness on four feet, the kind of thoroughbred whose refusal to be headed bespoke a will of iron. It was her weapon and she used it fiercely, like the Warrior Queens of myth and history. Boadicea would have happily ridden her into battle, that’s for certain.
2009: RACHEL ALEXANDRA (Medaglia d’Oro ex. Lotta Kim, by Roar)
It will be impossible for me to ever watch another Kentucky Oaks without carrying Rachel in my heart. Even though she would go on to great heights, culminating with her induction into the American Racing Hall of Fame in 2016, it is the Kentucky Oaks that I still watch, over and over again. With her mane flying, down the home stretch she came — and she owned me, body and soul, from that day forward. That race, at least for me, defined her. Bred by Dolphus Morrison, trained by Hal Wiggins and ridden by Calvin Borel, Rachel’s Oaks was also a victory for small breeding enterprises and successful, hard-working trainers and jockeys who seldom tumble into the spotlight.
It is so hard to know why some fillies go straight to your heart while others, themselves beautiful and brilliant, don’t. But in Rachel’s case, it was the kind of feeling associated with those of us who see in horses something otherworldly, embodying an essence that transports the human spirit. Watching her, I was overwhelmed by the conviction that this is what it must have been like to actually see a Man O’ War or Count Fleet in action. Too, I was reminded of Secretariat’s Belmont, of the exaltation of the soul watching a great thoroughbred running for the sheer love of it.
Watching Rachel cantering home on Oaks day, I was the little girl who played with Breyers and made up stories about them, and who shortened long trips in the car by imagining a beautiful, powerful horse running along beside me, jumping fences and floating over fields high with corn.
Rachel Alexandra took me home.
2010: BLIND LUCK (Pollard’s Vision ex Lucky One by Best of Luck, a son of Broad Brush out of Crowned, by Chief’s Crown)
The anticipation going in to the 2010 Oaks was huge. Two great fillies, Evening Jewel and Blind Luck, were anticipated to face-off in the run for the pink. Blind Luck’s come-from-behind running style was always risky, although she had won the Las Virgennes and the Fantasy by a hair’s breadth and would go on, after the Oaks, to victories of the same genre. Evening Jewel had the more conventional running form, moving into mid-pack and rating just off the pace before striking out for home. Blind Luck went into the Oaks’ the favourite, but I held my breath as the race got underway:
The challenge that Blind Luck and Evening Jewel threw down bespoke magnificence. Two brilliant fillies — one sweeping to the front from the tail of the field — going head to head, as the wire drew ever closer. For anyone unsure as to what “heart of a thoroughbred” looks like, this is it.
2011: PLUM PRETTY (Medaglia d’Oro ex Liszy, be A.P. Indy)
It was a young Martin Garcia and trainer, Bob Baffert, in the spotlight in 2011 when they brought Plum Pretty to the winner’s circle in the Oaks. I tuned in to see Zazu, Daisy Devine and Joyful Victory, and I don’t really remember knowing much about Plum Pretty, even though I was wise enough to respect any filly that Bob Baffert brought to the Oaks. Like so many Medaglia d’Oro’s, she was a striking filly with lots of scope and a fine head. But for all that, what lay within on that first Friday in May was so much more:
Plum’s Oaks might not have conjured the stuff of legend: she hung on to just win it. But the willingness to hang on, to do your very best, is a quality bred into the best thoroughbreds — and this was the signature of Plum Pretty’s 2011 Kentucky Oaks.
2013: PRINCESS OF SYLMAR (Majestic Warrior by A.P. Indy X Storm Dixie by Catienus, a son of Storm Cat)
Dreamers make-up at least 85% of the constituency of horse racing. These are the folks who take risks because they really believe that anything is possible and that dreams can come true.
Princess of Sylmar is a dreamer’s elixir: a filly who lacked a trendy pedigree and throughout most of her early, brilliant career was ignored because of it. Bred in Pennsylvania by Ed Stanco, “The Princess” raced in Stanco’s colours for his King of Prussia stable and was trained by Todd Pletcher.
In her second start at two, The Princess won a race at Penn National by nineteen lengths before moving to Aqueduct, where she won an allowance race by four under jockey, Rajiv Maragh. At this point, the filly was one of those hard-working girls running in small races that nobody much notices.
The filly kicked off 2013 with combined wins of fourteen plus lengths in the Busher and Busanda Stakes under jockey Javier Castellano. Moved up in class in The Gazelle, The Princess went down to defeat to Close Hatches and the loss caught people’s attention, likely resulting in her starting in the Oaks at 38:1 odds.
In a way, it was easy to ignore Princess of Sylmar, since the field included the Two Year-Old Eclipse Champion, Beholder. Too, both Dreaming of Julia and Close Hatches had distinguished themselves as very good fillies.
The start was unkind to Beholder, who fell in the Post Parade, throwing jockey Garrett Gomez. When the race was over, Gomez saluted Beholder for the way she had regained her composure, although he knew that she had quite possibly lost her Oaks at the gate. Dreaming of Julia got smacked at the jump out by Rose To Gold, impeding her chances of winning as well.
But was Princess of Sylmar’s win a fluke, at the expense of Beholder and Dreaming of Julia? It’s possible, but she defined herself in subsequent authoritative wins in the Coaching Club American Oaks, the Alabama and the Beldame, where she beat champion Royal Delta. When she finally met up with Beholder again, in the BC Distaff, The Princess failed to produce the kind of performance we had all come to expect from her. But, then again, she had had a long season by current standards.
Retired at the end of her four year-old season, Princess of Sylmar was sold to Shadai in Japan, where she delivered a colt by super stud Deep Impact in 2016. Princess of Sylmar was reportedly bred back to Deep Impact for 2017.
2016: CATHRYN SOPHIA (Street Boss by Street Cry X Sheave by Mineshaft)
She was another filly who, though not ignored by the punters, languished in the background, largely because of the hopes tied to Rachel Alexandra’s talented daughter by Bernardini, Rachel’s Valentina. And like so many who tuned in to watch that day, I was practically willing Rachel’s daughter to follow in her dam’s footsteps.
Cathryn Sophia was trained by the great John Servis, who conditioned Smarty Jones, another love of mine. Even though I favoured Rachel’s Valentina, my respect for Servis meant that I always paid attention to his runners and Cathryn Sophia was, indeed, very impressive. But when I read a column that quoted Servis as wondering whether or not his filly would stay the distance, I kind of pushed Cathryn Sophia off my radar. After all, her sire was a sprinter and Sheave, a daughter of Mineshaft (A.P. Indy) had beautiful bloodlines but Cathryn Sophia was her first foal.
Too, it was not as if there weren’t other serious challengers: notably, Land Over Sea, Lewis Bay and Terra Promessa, although the latter’s front-running style made her chances of taking it more risky than those of the other two.
But the Oaks played to Cathryn Sophia’s advantage, and Rachel’s Valentina seemed to have no more to give once the field turned for home. It was a thrilling finish, as the daughter of Street Boss danced away from the rest of the field:
Cathryn Sophia was retired in 2016, after a third place finish to Songbird in the G1 Cotillon. She was bred to Pioneerof the Nile in 2017.
With Cathryn Sophia’s win I was reminded of those fickle racing gods, who never fail to make me doubt myself, while assuring that each Kentucky Oaks is an adventure in its own right.
Thoroughbred racing is more often than not the theatre par excellence of sports. With their rich history and tradition, classic races like the Oaks are punctuated by triumph and loss, and the promise of hope and possibility. The dramatis personae may change from one year to the next, but the tone and message endure.
On Oaks day, these elements help to construct a rare opportunity — that of slipping away from daily cares to take your place in a country of dreams, dreamers and magnificent fillies.