Who Is the greatest Saratoga Special winner?

August 10th, 2021

The Saratoga Special S. had some truly special rules through the first half-century of its existence.

From its beginning, in 1901, through 1959, owners could nominate horses in sets of three, but each owner could only run one horse in the race. And, instead of the purse being split among the first few horses to cross the wire, the winner took it all. A head bob didn't just mean a lot — it meant absolutely everything.

But when a race at Saratoga means so much, it attracts confident owners who run their best horses, and its winners list reads as a list of all-time greats.

Take a look back at the best of the best to win the Saratoga Special and then you tell us — who is the greatest of them all?


In the 1907 Saratoga Special, Colin faced a match race against Uncle, a horse who had sold for a mind-boggling $30,000 before the race.

Colin couldn't read a price tag.

Uncle kept tabs most of the way, but Colin edged away late to prevail by a length.

Of course, Colin was special. Very few horses retire undefeated. Even fewer do so after they face the best of the best.

In 15 starts across ages two and three, including 14 in stakes company, Colin did everything asked of him. He won going as short as five furlongs and as long as 11, the distance of the Belmont Stakes at the time.

He was not only the champion of his age group at both two and three, but Horse of the Year both times, too.

Native Dancer

The "Grey Ghost" started his career with a bang, with wins in all nine of his juvenile tries. That included a muddy edition of the Saratoga Special, which he won by 3 1/2 lengths at odds-on.

His dominant juvenile campaign made him the consensus champion of his age group, and two of the three major polls named him Horse of the Year in 1952.

He fell a head short to longshot Dark Star in the Kentucky Derby but still won the rest of his races, including the Preakness and the Belmont, to claim champion three-year-old.

At four, despite injuries, his wins included the Metropolitan H. and he claimed both champion older horse and Horse of the Year. 


In 1914, Regret became the first horse to sweep Saratoga's trifecta of juvenile stakes races — the Saratoga Special, Sanford S., and Hopeful S. Only three horses have done so since (Campfire, Dehere, and City Zip), and they were all males.

The Saratoga Special was run first in Regret's day, and she debuted in the race. Still, she led every yard and won by a length.

After her trio of wins at Saratoga, she didn't resurface again until the Kentucky Derby, and she won that, too.

A lightly raced mare, Regret raced through age five, though only ran 11 times in total. But her nine wins — plus her tough, nose defeat in the 1917 Brooklyn H. — were enough to mark her one of the best of the American turf.


Sysonby came into the 1904 Saratoga Special undefeated in three starts and was hardly extended in the Special. He cantered home six lengths clear of Hot Shot.

Though he was defeated for the first and only time next out, in the Futurity S. at Sheepshead Bay, he was beaten by the filly Artful. Though Artful entered that race a maiden, she was an eventual Hall of Famer, just like Sysonby.

In one more start at two and then nine at age three, Sysonby never lost again. That included a dead-heat victory, when he made his three-year-old debut against older in the Met Mile.


Whirlaway gave his backers some tense moments in the 1940 Saratoga Special. He drifted out, hit the outside rail, and lollygagged on the lead, but he got to the wire first.

He went on to hit the wire first a lot more, including in all three Triple Crown races the following year, as well as the Travers S.

He was a champion at ages two, three, and four, and also Horse of the Year at three and four.

And, if you're in Chicago, Have a drink at the Whirlaway Lounge, which legend has it, was built with winnings from a bet on Whirlaway early in his career.

Last week, we asked your favorite racetrack tradition! All five got some love. But, with 40% of the vote, your favorite rang clear as a bell — specifically, the bell in the winners' circle at Saratoga, which sounds at 17 minutes to post.