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Why do Blue Grass winners fail in the Derby?

Make no mistake, the Toyota Blue Grass Stakes is a good race to win.

It's a Grade I, after all. It's also the best race at the best track in the best place to breed and sell horses in these United States, if not the world.

"It's like having a tryout on Broadway," said Joe Drape, racing writer for the New York Times, and author of To the Swift and The Race for the Triple Crown. "That's where all the buyers are."

So why is it that, with the 86th running of Keene land's spring jewel on Saturday, for the past 18 years the winner of the Toyota Blue Grass Stakes has had nothing to do with the winner of the Kentucky Derby?

Thumb through the record books back to 1991 and Nick Zito's Strike the Gold to find the last Blue Grass winner who also hit the wire first at Churchill Downs on the first Saturday in May.

A third-place finish by Peace Rules in 2003 was the last Blue Grass winner to hit the Derby board. Nine of the last 10 Blue Grass winners failed to finish better than fifth at Churchill. None of the last five finished better than 10th.

Since Strike the Gold's win, only three Derby winners ran in the Blue Grass — Sea Hero in 1993, Thunder Gulch in 1995 and Street Sense in 2007.

What in the name of Polytrack gives?

Well, it's not Polytrack. Not entirely. The Derby drought originated long before Keene-land installed its synthetic surface four years ago.

"I think, even before the synthetic surface was put in, winners of the Blue Grass in the early part of the 2000s were viewed as winners on a speed-favoring track," said Jay Privman of the Daily Racing Form. "The dirt era of the Blue Grass went out in a blaze of glory with Sinister Minister."

Sinister Minister was the Bob Baffert-trained speed demon who won the 2006 Blue Grass by 12¾ lengths, only to finish 16th in the Kentucky Derby.

But Sinister Minister illustrates another problem, as well. Baffert threw his horse into the race at the last minute, in hopes that a strong showing would lead to Louisville. It's a familiar refrain for what is now one of the last Derby preps.

"It seems to be the last chance to get in," Drape said. "You look at the horses this year. And last year you had General Quarters, before that Sinister Minister and horses like that. It always seems like Todd Pletcher is sending his fifth- and sixth-best horses. They're catch-up horses that are not really contenders."

Many contenders run fewer races on earlier dates. The modern way is to leave more time between a horse's final Derby prep and the Derby itself.

"There's so many ways now to get to the Derby," Privman said. "The methodology of the Derby has changed so much in the last two to three decades."

That doesn't explain why the Arkansas Derby, run the same day as the Blue Grass, has been a better predictor. Three Arkansas Derby winners have captured five Triple Crown races. Smarty Jones won the 2004 Derby and Preakness. Afleet Alex won the 2005 Preakness and Belmont. Curlin won the 2007 Preakness.

"And Oaklawn is kind of configured like Churchill," Drape said. "Its surface is like Churchill, and it's dirt."

So it could be the Polytrack, considering the last three winners — General Quarters, 10th in 2009; Monba, 20th and last in 2008; Dominican, 11th in 2007 — all flopped in the River City.

"I think there is still a feeling-out process with the synthetic surface," Privman said. "On dirt, they have a higher level of confidence of how much more they need to do, or less they need to do."

Or maybe the Blue Grass drought is overblown.

"After all," said Privman, who is based in California, "no winner of the Santa Anita Derby has won the Kentucky Derby since 1989. And that's still an awfully good race."

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