The making of 'Legends'

LEXINGTON, Ky. -- Olin Gentry guides his black Infiniti QX56 slowly through the steady April rain, enthusiastically pointing out landmarks.

Over there are the four surviving marble columns from Green Hills, the original mansion on Elmendorf Farm, a famed thoroughbred breeding operation set on rolling bluegrass and now being leased by Gentry and his business partner, Thomas Gaines. Over here are the graves of several prominent race horses and stallions. Back by the black split-rail boundary fence there once was a train station, where decades ago they loaded the yearlings for transit to the sales in Saratoga Springs, N.Y.

And down the way is one of the barns where they keep the current yearlings.

Gentry parks the SUV and walks into the barn. There he proudly shows off a four-legged collector's item: the last living colt produced by Storm Cat, one of the greatest sires in breeding annals. A groom walks the colt back and forth, showing off his conformation and coordination.

"He's the end of the sire line," says the 43-year-old Gentry, an affable third-generation horseman who loves Winston cigarettes and Kentucky basketball almost as much as thoroughbreds.

All three of the stable's superstar trainers -- D. Wayne Lukas, Bob Baffert and Nick Zito -- will saddle horses in the Derby. But none will wear the blue and white silks of Thoroughbred Legends Racing.

In another stall is a strapping colt from the first foal crop of 2007 Kentucky Derby winner Street Sense. Across the barn is a son of two-time Breeders' Cup Classic winner Tiznow, now a star stallion. They'll go to auction in a few months, with hopes of fetching big prices.

The farm has a grand past. The yearlings represent a promising future.

The present is another matter. The present stings a bit. The present is Kentucky Derby week, and it offers vivid evidence of how brutally hard it is even for learned horsemen with a lot of money to win a Derby -- or to simply reach the starting gate.

On Wednesday, post positions were drawn for the 20 entries in the 136th Derby. Gentry and Gaines' ambitious fledgling ownership syndicate, Thoroughbred Legends Racing Stable, is not among them.

All three of the stable's superstar trainers -- D. Wayne Lukas, Bob Baffert and Nick Zito -- will saddle horses in the Derby. But none will wear the blue and white silks of Thoroughbred Legends Racing.

"It's been tough," Baffert acknowledged.

"Not only do you have to get the right horse," Gentry said. "You have to get the right management, and you have to get the timing right. It all has to be there."

Legends' Derby shutout is due largely to bad luck and bad timing, certainly not due to a lack of effort or expenditure. Backed by a significant amount of investor capital, Legends spent more than $15 million on 38 yearlings -- 28 colts and 10 fillies -- in the summer of 2008 and dispersed them to the three most accomplished Triple Crown trainers in the sport. Between them, Lukas, Baffert and Zito have won nine Kentucky Derbies and 26 Triple Crown races.

Attention from The Wall Street Journal, Bloomberg News and multiple thoroughbred publications accompanied the buying spree, and the unique trainer alliance. According to BloodHorse.com, the $15,285,000 spent ranked Legends second on the leading buyers' list for North American yearling sales based on gross expenditures.

"They made a big splash," Zito said.

The aim, as stated on the Legends website, was not modest: "Developing America's largest, most successful Thoroughbred racing stable. The stable will acquire, train and race the best bred and best conformed prospects in large numbers with the goal of developing racing champions and sire prospects."

The targeted initial impact: right now.

All those yearlings purchased in '08 are now 3-year-olds, and 12 of them were nominated for the 2010 Triple Crown, the most nominees of any single ownership. Yet the $15 million worth of horse flesh has earned Legends less than $1 million in purse money, and has not come close to winning the stable a significant Derby prep race.

Only one Legends horse -- The Program, trained by Baffert -- ran in a major Derby prep. He finished seventh in the Louisiana Derby in March, pushing him off the Kentucky Derby trail. Seventeen of the horses remain unraced. And Legends' four million-dollar yearlings have produced a total of $2,160 in purse money.

Alcindor was a $1.15 million purchase sent to Lukas. A more appropriate name might be "Milicic" -- the colt has yet to make his racing debut.

Lukas also had $1.2 million yearling Lambeau Legend. He raced three times at age 2 and finished no better than fifth in maiden races. He hasn't been heard from since. Gentry's succinct summation: "Sidelined."

Baffert's two seven-figure horses, Flagship and Temp, also are unraced after encountering some minor injuries that inhibited their development.

They are hardly the first expensive horses who have been slow to mature or failed altogether as racers. Coolmore, the massive Irish racing conglomerate, once paid a record-smashing $16 million for a single horse -- atrociously named The Green Monkey -- and the animal was retired after three winless starts. Sheikh Mohammed bin Rashid Al Maktoum, the ruler of Dubai, has spent untold millions in an attempt to win a Kentucky Derby without ever having finished better than sixth.

Then again, sixth in the Derby would sound pretty good to the Legends folks right about now.

"You've got to be really lucky to buy horses and get to the races," Zito said. "And you've got to be even luckier to get to the Derby. It's the greatest game played outdoors, but 90 percent of the time you're explaining failure.

"Mr. Gentry and Mr. Gaines, they're good people, good for the game. They're trying hard to stay in the game right now, and they're smart enough to know this thing can turn around."

Gentry is bullish on the future for Alcindor, Flagship, Temp and several other Legends 3-year-olds. He ticked off a list of 10 horses he strongly believes will deliver big things down the road, possibly by the Breeders' Cup in the fall. He stressed that Legends could have pushed unprepared horses toward the Derby if they had wanted to, but instead exercised patience.

It's the greatest game played outdoors, but 90 percent of the time you're explaining failure.

-- Trainer Nick Zito

"If you try to cheat time with horses, you've got nothing," Gentry said. "You've got to let it happen."

But everything about Legends' pitch to investors said that the spring classics were the primary goal. The Legends promotional video opens with a shot of Churchill Downs' Twin Spires at dawn, and proceeds to show Lukas, Baffert and Zito winning the Derby, Preakness and Belmont with a variety of horses.

The inference is clear: We're going after the Triple Crown races.

"We took a flyer," Lukas said. "We went for it, we bought nice horses, and it just didn't work."

It especially did not work for Lukas, the 72-year-old who has won four Derbies and 13 Triple Crown races. He started with $5.9 million worth of Legends horses, but said in mid-February he received an apologetic call from Gentry saying that Legends was taking its horses out of his barn after virtually all of those that raced performed poorly.

"I'm not even in that thing anymore," Lukas said. "That's how big a swing and how big a miss it was."

Gentry confirmed that Lukas no longer has the Legends horses in his barn, but said they have simply been sent to a farm to freshen up before returning to training.

"Wayne's still in the deal, and I plan on him continuing to be," Gentry said. "Wayne and I go back to when I was a kid. Wayne Lukas, to me, was magic, and truly one of my heroes."

Baffert trained the one star of the stable, a speedball named Conveyance. The colt was a $240,000 yearling purchase who won his first two races. But after the second win in November, Legends was made an undisclosed but lucrative offer by Zabeel Racing International -- an operation founded by Sheikh Mohammed's oldest son.

Gentry, Gaines and their partners had little choice but to sell. Legends' investment war chest had never gotten as big as was originally intended to, thanks to the global recession that hit within weeks after it made its flashy entry into the game. That kept Legends from making any yearling purchases in 2009 and left it cash-strapped last year.

"Who knew the world economy was going to implode right as we're launching?" Gentry asked. "That kind of took the wind out of our sails."

So Conveyance was sold. Naturally, he went on to win his next two races and then finished second at the Sunland Derby in March. The colt will run in the Derby -- beneath the silks of Zabeel, not Legends.

"We're proud of him," Gentry said. "He is, in my mind, a Legends horse. We don't own him, but he's part of our program.

"We knew he was a good horse. We made a good deal on him and were happy. With the deal we got, it probably would have been a little irresponsible of us not to sell him."

So Gentry will make his 34th consecutive Kentucky Derby appearance Saturday without a horse, but also without seller's remorse. A guy who says he "grew up in a barn" and used to beg to be awakened anytime one of his father's mares gave birth knows the sport's peaks and valleys as well as anyone. But he's an optimist and a racing romantic at heart.

He sees peaks ahead, predicting that Legends will be back in a big way at the summer yearling sales. And he predicts future breeding success for Legends horses, which could be where the really big bucks are earned.

"Within the industry, [the Derby] is not the end-all," Gentry said. "Having said that, there is no better trophy to win. And I think we will win it, eventually."

If that day does come, Gentry will lead another excursion across Elmendorf Farm to another landmark. There is a bell out there, atop scaffolding some 15 feet above the ground. It was erected by James Ben Ali Haggin, who bought the farm in 1897.

According to local lore, Haggin decreed that the bell was not to be rung until the farm had produced a Kentucky Derby winner. Legend has it that it's never been rung.

One day the bell could toll for thee, Olin Gentry. But there's a good reason it hasn't tolled in all this time, and you know it as well as anyone: Winning the Derby is hard to do.

Pat Forde is a senior writer for ESPN.com. He can be reached at ESPN4D@aol.com.