Ranking the 10 Best Preakness Winners Who Weren't Kentucky Derby Champions

With the 138th running of the Preakness Stakes drawing near, contenders are coming out of the woodwork to take on Kentucky Derby champion Orb and thwart his bid for the second jewel of racing's elusive Triple Crown.

Historically, the Preakness Stakes has a strong record of producing winners who either lost or did not compete in the Kentucky Derby. Some of horse racing's all-time greats may have lost the battle in Louisville, but went on to win the war after getting redemption in Maryland.

Here are the 10 best horses who went on to win the Preakness after either losing or skipping the Kentucky Derby.

10. Bernardini: 2006

Bernardini's victory in the Preakness Stakes will forever have a dark cloud over it.

Though it was a coming-out party for Bernardini, the late-developing, impeccably-bred star on the rise, it was also the race where America's Kentucky Derby hero Barbaro suffered a catastrophic injury.

But Bernardini's triumph in Maryland was not a fluke performance. After his resounding victory in the Preakness Stakes, the powerhouse colt went on to win three major-stakes races, including the prestigious Travers Stakes and the Jockey Club Gold Cup.

In the final race of his short but exciting career, he thrilled America with a battle against the Argentinian star Invasor in the Breeders' Cup Classic, though he had to settle for second.

His real success has come thus far in the breeding shed, as Bernardini has become one of the most expensive and prolific sires in the sport. 

9. Bold Ruler: 1957

After winning the Wood Memorial in 1957, Bold Ruler wound up fourth as the favorite in the Kentucky Derby. It was a disappointing showing for the Wheatley Stables home-bred, but he quickly made amends for that in the Preakness Stakes.

After his victory in Maryland, the colt went on to become one of the most successful handicap horses of the 1950s, winning prestigious New York races and earning champion three-year-old honors along with champion sprinter the following year. 

His greatest achievement, however, came in the breeding shed. He sired the legendary Secretariat, and this year's Kentucky Derby winner, Orb, can be traced back to him as well. 

8. Nashua: 1955

Not many horses get a chance to avenge their loss in the Kentucky Derby quite the way Nashua did.

After finishing second to Swaps in the 1955 Kentucky Derby, Nashua went on to take the remaining two legs of the Triple Crown, the Preakness Stakes and Belmont Stakes.

Later that summer, he and Swaps met again in the Washington Park Match Race to decide once and for all who was the superior three-year-old colt that year.

Nashua won, cementing his status as champion sophomore and earning Horse of the Year honors for the year after finishing the season with nine wins from 11 starts.

7. Lookin at Lucky: 2010

Lookin at Lucky lost all chance in the Kentucky Derby the moment he was assigned the dreaded inside-post position in the field of 20.

The highly regarded, Bob Baffert-trained colt was clobbered coming out of the gate, and the best he managed was a troubled sixth-place finish. For a colt who had shown so much talent, it was a tough and very disappointing loss.

Two weeks later, he came to Maryland and authoritatively defeated a field of 11 rivals to claim his own jewel of the Triple Crown. He went on to win two more races that year, including the prestigious Haskell Invitational, before finishing fourth in a star-studded Breeders' Cup Classic. 

6. Rachel Alexandra: 2009

After demolishing a field of female rivals in the Kentucky Oaks, the decision was quickly made that Rachel Alexandra would take on the boys two weeks later in the Preakness Stakes.

Prior to the Preakness, she had been regarded as a freakishly talented filly who had yet to face any serious competition. After her 20 1/4 length tour de force in the Oaks, she was purchased by Jess Jackson's Stonestreet Stables with the intent of proving just how good she really was.

And prove they did.

She defeated a field of 12 male rivals, including upsetting Kentucky Derby winner Mine That Bird by a length, to secure her place in the history books.

After that victory, she went on to remain undefeated in 2009 and defeated male rivals twice more, in the Haskell Invitational and Woodward Stakes.  

5. Afleet Alex: 2005

Afleet Alex is a length away from being a Triple Crown winner. 

Going into the Kentucky Derby, he was somewhat overlooked and went off as the second choice behind the much-hyped Bellamy Road. Turning for home, he launched a strong bid and wound up getting caught by two massive long shots, Giacomo and Closing Argument.

Two weeks later, he was back in the Preakness Stakes for one of the most memorable installments of the Maryland tradition in history.

At the top of the stretch, he was set to engage the long-shot leader Scrappy T when that rival suddenly ducked out, causing Afleet Alex to clip heels, stumble and nearly go down.

The sheer display of athleticism and class that he displayed to right himself and still go on to win was the stuff of which legends are made.

After that triumph, he went on to win the Belmont Stakes in the final start of his career.

4. Curlin: 2007

After a competitive third against a deep, talented field in the Kentucky Derby, Curlin came back in style two weeks later in the Preakness Stakes.

After stumbling at the start, the big chestnut gallantly denied the Kentucky Derby champion Street Sense the second jewel of the Triple Crown, prevailing by a head in a thrilling stretch duel.

This colt was no stranger to a battle going into the Belmont Stakes, though this time he wound up on the losing end of the photo finish to super-filly Rags to Riches in a race for the ages.

After a third-place finish in the Haskell Stakes, Curlin went on to dominate the remainder of his three-year-old season, capping it off with a victory in the Breeders' Cup Classic.

As an older horse, he was ambitiously campaigned and raced to international success in the United Arab Emirates with a stirring victory in the Dubai World Cup. Back in the United States, he won two other Grade 1 races that year and retired as the North American all-time leading money-winner with an impressive $10,501,800 in earnings.

3. Point Given: 2001

Point Given had all of the goods to be a superstar.

After suffering a nose-defeat in the Breeders' Cup Juvenile, he wheeled back in December to add another Grade 1 to his already impressive resume, hinting at things to come as a three-year-old.

In 2001, he returned as a sophomore with a vengeance—bigger, tougher and even better. After rattling off back-to-back victories in key West Coast Kentucky Derby preps, the Bob Baffert-trained colt went into the Kentucky Derby as the heavy favorite.

After getting bumped at the start, he wound up a non-threatening fifth in what would be the only off-the-board finish of his career. 

Convinced that he was better than that lackluster performance, he and Bob Baffert headed to Maryland with something to prove. All questions were answered when Point Given rolled to a dominant victory in the Preakness and went on to win the Belmont Stakes, the Haskell and the Travers.

2. Native Dancer: 1953

The only race in Native Dancer's remarkable 22-race career he ever lost was the Kentucky Derby.

After a roughly run, disappointing second-place finish in the Run for the Roses, the iconic gray colt nicknamed "the Gray Ghost" never lost again.

He captured the Preakness and the Belmont Stakes en route to earning his second championship. In 1952, he had been named the nation's top juvenile and took home three-year-old honors as well.

He made one final start as a four-year-old, winning the historic Metropolitan Handicap, and remains one of the sport's all-time greats. 

1. Man O' War: 1920

There are few horses who became household names and transcended the sport, but the immortal Man o' War did just that.

He became a star of the 1920s and was as recognizable to sports fans as Babe Ruth. To this day, he ranks as one of the all-time greatest horses to ever look through a bridle. 

However, he did not win horse racing's marquee event. In fact, he did not even compete.

Physically, the original "Big Red" was an imposing figure, and instead of rushing the maturing colt into the grueling 1 1/4 mile test of the Derby, his trainer opted to sit out the Run for the Roses and aim for the Preakness Stakes.

His patience was rewarded, and Man o' War remained undefeated for the rest of his career, capturing both the Preakness and Belmont Stakes on his race into the history books.