Curlin: What it Takes to Win Horse of the Year — Twice

Curlin wins the 2008 Woodward Stakes. (Photos by Eclipse Sportswire)

Just about the only thing Curlin did not do in his fabulous career was end “The Curse of Apollo.”

A horse who did not race at 2 had not won the Kentucky Derby since the aforementioned Apollo all the way back in 1882, and Curlin gave it the old college try to end the jinx that Triple Crown winner Justify eventually halted in 2018.

Curlin made his debut on Feb. 3, 2003 and then ran third three months later in the Kentucky Derby.

Yet after that first Saturday in May, there was no stopping Curlin.

He won the Preakness by a head and was quickly on his way to a career that would see him become a two-time Horse of the Year and retire as the sport’s all-time leading money earner with $10,501,800 (Curlin still ranks in the top 10 by lifetime earnings).

As they say, better late than never.

A son of Smart Strike out of the Deputy Minister mare Sherriff’s Deputy, Curlin was bought as a yearling for $57,000 by the Midnight Cry Stable of William Gallion and Shirley Cunningham Jr., class-action attorneys in Kentucky.

Trained initially by Helen Pitts, Curlin romped by an eye-popping 12 ¾ lengths in his debut at Gulfstream Park.

It was the kind of debut that instantly sparked Triple Crown dreams and came at a fortuitous time for Gallion and Cunningham who would eventually land in jail for allegedly pocketing $90-million from a $200-million class-action settlement they arranged.

Attracted by the promise they saw in Curlin, a group consisting of Jess Jackson, the founder of Kendall-Jackson wines and Stonestreet Stables, Satish Sanan, and George Bolton gave the Midnight Cry duo $3.5-million for an 80% share of Curlin.

The initial reward was a 5 ¼-length victory in the Grade 3 Rebel Stakes at Oaklawn Park in Curlin’s initial start for his new connections and trainer Steve Asmussen. A smashing 10 1/2-length victory in the Arkansas Derby was next and it paved the way for Curlin to be sent off as the 5-1 second choice in the 2007 Kentucky Derby.

Apollo’s jinx seemed to be on the ropes, but Curlin had some traffic issues early on and, though he closed quickly in the stretch, he had to settle for third behind the victorious Street Sense, who broke a hex of his own by becoming the first horse to win both the Breeders’ Cup Juvenile and the Kentucky Derby.

In the Preakness, Street Sense seemed home free in midstretch but this time Curlin’s furious late charge paid off as he got up in the final strides to win by a head.

Without a Triple Crown on the line, Street Sense skipped the Belmont Stakes but the lightly raced Curlin moved on to New York. There he wound up in a classic stretch duel with the filly Rags to Riches, who prevailed by a head to end a longer jinx than Street Sense did, as she became the first filly to win the Belmont since 1905.

Exiting the Triple Crown, the 3-year-old crop of 2007 boasted four exceptional males in Street Sense, Curlin, Hard Spun, and Any Given Saturday, all of whom were destined to battle it out to the Breeders’ Cup to decide the division championship.

The first post-Triple Crown showdown came in the Haskell Invitational, which Any Given Saturday won by 4 ½ lengths over Hard Spun, the Kentucky Derby runner-up who beat Curlin to the finish line by a head.

While Street Sense won the Travers Stakes, Curlin took two months off and returned to face his elders for the first time, bravely winning the Jockey Club Gold Cup by a neck over Lawyer Ron.

It then came down to the Breeders’ Cup Classic to determine not just the champion 3-year-old but Horse of the Year as well. On a sloppy racetrack at a rain-soaked Monmouth Park, Curlin and regular rider Robby Albarado splashed to a 4 ½-length win over Hard Spun with Street Sense fourth and Any Given Saturday sixth.

“It’s incredible," Asmussen said after the Classic. "It’s all about Curlin. He’s the one who did it. [The track] was a huge concern. I was extremely nervous about it, extremely nervous. Robby gave him the chance. He got him on his feet. First time by [the stands], he was carrying Robby nicely, and he ran extremely well from there. He is an incredible horse.”

Curlin after winning the Breeders’ Cup Classic. (Eclipse Sportswire)

Horse of the Year belonged to Curlin, and 2008 seemed his for the taking as well with Street Sense headed to the breeding shed.

Yet rather than bully U.S. rivals at the start of 2008, Jackson sent his star overseas in search of bigger challenges and after a victory in a prep race at Nad Al Sheba, he romped in the $6 million Dubai World Cup by a record-smashing 7 ¾ lengths.

"What a horse," Albarado said. "Curlin is like a limousine and I am just along for the ride."

Back in the United States, Asmussen sent Curlin out in the Grade 1 Stephen Foster Stakes and he responded with a 4 ¼-length victory.

Jackson opted for a different challenge in Curlin’s next start and ran him on the turf in the Grade 1 Man o’ War where he was second to Red Rocks.

Back on the main track, Curlin posted wins in the Woodward Stakes at Saratoga and Jockey Club Gold Cup and headed to Santa Anita Park for a second trip to the Breeders’ Cup Classic.

This time, though, the Classic was contested on a synthetic surface that he did not relish and he finished fourth in his final career start.

The loss, however, could not diminish what Curlin did that year and he was once again voted Horse of the Year, beating the 3-year-old Kentucky Derby and Preakness winner Big Brown and an undefeated filly named Zenyatta.

It was a fitting honor to close out a career that was absolutely brilliant.

“Curlin showed the heart of a champion in every race,” Jackson said prior to the 2008 Eclipse Awards. “He did everything we asked of him and more — taking on ever-more difficult challenges. He won going away, he won coming from behind, he won in the heat and in the rain.”

Take that, Apollo.

Note: This story was originally published in 2016 and has been updated.

Fun Facts About Curlin

  • Curlin, Wise Dan, Secretariat, Forego, Affirmed, and Cigar are the only horses to win Horse of the Year honors in back-to-back years since the Eclipse era started in 1971. Curlin was elected to the National Museum of Racing's Hall of Fame in 2014.
  • Curlin was the fourth horse to win the Breeders' Cup Classic and the World Cup the following year, joining Cigar, Pleasantly Perfect, and Invasor. Arrogate became the fifth in 2017.
  • After retiring, Curlin became one of the leading sires in North America. His top progeny include champions Vino Rosso, Good Magic, and Stellar Wind, 2013 Belmont Stakes winner Palace Malice, 2016 Preakness Stakes winner Exaggerator, and 2021 Longines Kentucky Oaks winner Malathaat.

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