2011 Preakness Stakes: 5 Best Derby Winners To Lose the Preakness

Since World War II, just 23 of the 65 Kentucky Derby winners have run back and won the Preakness Stakes, a rate of barely greater than one-in-three. Included in those 23 are five Triple Crown champions: Assault, Citation, Secretariat, Seattle Slew and Affirmed.

But that leaves 42 Derby champions that did not win the Preakness.

While a few skipped the Preakness for a variety of reasons, such as Grindstone to injury, Spend a Buck due to a high-money appearance in the Jersey Derby and Swaps because he wasn't nominated, the vast majority did run back at Pimlico. And save 23 of them, they all lost.

Later in the week, we'll rate the 42 Preakness winners who didn't win the Derby. But for now, let's look at those those 42 Derby winners that didn't win the Preakness.

Here are the five best Derby winners since World War II to run back at Pimlico in the Preakness and lose.

5. Swale (1984)

The son of Seattle Slew was a prohibitive favorite to win the Preakness Stakes after he crushed the field in the Kentucky Derby two weeks earlier.

Swale had eight wins from 12 starts and had never finished out of the money, making him the easy choice at Pimlico. But he didn't fire, running seventh, a result that jockey Laffit Pincay and trainer Woody Stephens blamed on a hard track.

It was an uncharacteristically poor performance for the champ, and he bounced back in style.

Despite temperatures in the 90s in Elmont, N.Y., Swale put in his best performance, triumphing in the Belmont Stakes by four lengths in the fourth-fastest time on record. No one else had even the hope of a chance.

But instead of getting better, that was it for Swale.

Eight days after his Belmont win, Swale went for a jog at Belmont. Everything went swimmingly. He was walked back to the barn and bathed as was routine.

Then, all of a sudden, he collapsed, dead before he even hit the ground.

Still to this day, no one knows why he died, as the autopsy came up empty.

4. Ferdinand (1986)

From 1987 to 1990, all four Breeders' Cup Classic winners were former or reigning Kentucky Derby champions. No Derby winner has won the Classic since.

The first of those, Ferdinand, won the Derby in 1986, the fourth triumph for jockey Willie Shoemaker and his first in over two decades.

But he wasn't the favorite for the Derby, or even anything close to it. Ferdinand was a prohibitive outsider, going off at 17-1. But Shoemaker rode him along the rail splendidly.

Snow Chief, the beaten favorite, earned his revenge on Ferdinand in Baltimore, but Ferdinand would only get better.

At four, he won numerous major stakes races, including the Hollywood Gold Cup, before closing out the year with a victory at Santa Anita in the Breeders' Cup Classic. The win sealed up 1987's Eclipse Award for Horse of the Year and Ferdinand's place in history.

He struggled at five and was retired to stud in 1988.

3. Foolish Pleasure (1975)

A champion at two, Foolish Pleasure dominated two of the biggest prep races, the Flamingo Stakes at Hialeah and the Wood Memorial at Aqueduct, before a comfortable win in the Kentucky Derby.

In the Preakness, Foolish Pleasure came after Master Derby like he had in Louisville, even appearing to draw even past the 16th pole. But he couldn't get by and Master Derby re-rallied to win by almost a length.

That summer, Foolish Pleasure beat the filly Ruffian after Ruffian broke down in their famous match race and came back strongly at four.

A sore hoof delayed his four-year-old stakes debut, but when he was healthy he was much the best in the Donn Handicap at Gulfstream, winning despite carrying 129 pounds.

After a few tough losses, including the Met Mile at Belmont to Hall of Famer Forego, Foolish Pleasure came back in the Suburban Handicap to deny Forego a sweep of the three big New York handicap races.

It was his last great win.

2. Genuine Risk (1980)

No filly had run in the Kentucky Derby in 21 years by the time that Genuine Risk stepped into the gate. The only filly to win the Derby? Well, that would have been Regret in 1915.

But win the Derby Genuine Risk did, and she wasn't done.

As they turned for home in the Preakness, Genuine Risk was coming to the outside of Codex with a burst of speed. But Codex went wide, forcing Genuine Risk wide as well. Codex strolled home over Genuine Risk.

The stewards deemed no foul occurred, yet the case was not over.

Diana and Bertram Firestone, the owners of Genuine Risk, appealed the decision to the state racing commission, arguing that Genuine Risk had been forced wide, jostled and struck by the whip of Codex's jockey Angel Cordero.

Nonetheless, the commission voted 3-1 to uphold the ruling of the stewards on June 2, just a few days before the Belmont.

Genuine Risk ran second there too, becoming the only filly ever to finish in the money in all three Triple Crown races, let alone in the top two in every race.

1. Riva Ridge (1972)

If you watched the Secretariat movie, you would have no idea that Riva Ridge won the 1972 Kentucky Derby. I mean, why should the movie touch on the horse that won the Derby the year before Secretariat? They had nothing in common.

Well, nothing except that both Riva Ridge and Secretariat were homebreds for Christopher Chenery's Meadow Stable, trained by Lucien Laurin and ridden to glory by Ron Turcotte.

I guess we can cut the movie a little slack for ignoring a Kentucky Derby winner so integral to the entire story.

But Riva Ridge was a legend in his own right, winning the Derby under a hand ride.

He was never to be confused as a mudder, struggling in the Preakness. Bee Bee Bee, a Maryland-bred horse, shocked the world, while Riva Ridge lost a photo for third with Key to the Mint.

Viva Riva came back though and won the Belmont by seven lengths and then was the top older horse in 1973 while Secretariat embarked on a Triple Crown championship.

It's easy to forget Riva Ridge when a movie about his farm ignores him. But he is the best Derby winner since World War II to lose the Preakness Stakes.