The Greatest Rivalry That Never Was

When the younger generation of racing fans see this headline they naturally would think the column is about Zenyatta and Rachel Alexandra. But most of them probably have no conception of what it was like back in 1966 when Buckpasser and Graustark appeared to be on a collision course that would lead to a much-anticipated showdown in the Kentucky Derby.

Both homebred colts came from powerhouse private stables – Buckpasser owned by Ogden Phipps and Graustark owned by John Galbreath’s Darby Dan Farm.

As they began their respective journeys on the Derby trail, Buckpasser had a huge edge on experience and proven class, having won nine of his 11 starts at 2, including come-from-behind victories in the National Stallion Stakes, Tremont Stakes, Sapling Stakes, Hopeful Stakes, Arlington-Washington Futurity, and Champagne Stakes. His only two defeats came in his career debut when he raced greenly and a shocking upset at 3-5 in the Futurity Stakes at Aqueduct when he couldn’t get past Hirsch Jacobs’ dynamic filly Priceless Gem, who held him off to score by a half-length.

Graustark was sent to Arlington Park with Loyd “Boo” Gentry’s second string and the word was out on him right from the start, especially after he worked five furlongs in the mud in :58 2/5 breezing. The question was, what was this regally bred son of Ribot doing at Arlington with Gentry and not with the main string trained by Jimmy Conway, who two years earlier had won the Kentucky Derby and Belmont Stakes for Darby Dan with Chateaugay.

Graustark, named after novelist George Barr McCutcheon’s series of books set in the fictional country of Graustark, was so highly touted by clockers he was sent off at 1-5 in his career debut, despite the presence of two horses coming off good second-place finishes, and coasted to an easy seven-length victory. Entered next in an allowance race, he was such a sure thing the race was run as an exhibition. As in his debut, he dueled for the early lead and then drew off with ridiculous ease to win under wraps by nine lengths.

A big imposing liver chestnut with a gargantuan stride, it usually took him a quarter mile to get in gear, and once he did he took off and left his opponents far behind in a flash.

Watching these races with great interest and indignation was Conway, who accused Gentry and his uncle, farm manager Olin Gentry, of hiding Graustark from him. Olin was a tough old hardboot who had run Idle Hour Farm for Col. E.R. Bradley and he knew what they had early on. Anyone who knew him would have no doubts he would want nothing more than to have his nephew train this spectacular-looking colt. When he complained, Galbreath offered to give him the colt, but he was already soured by the occurrence and didn’t want to take the horse from Gentry. He felt he had no other recourse but to resign, leaving Boo Gentry with the main string of Darby Dan horses.

It was then time to try stakes company in the six-furlong Arch Ward Stakes, which was to be a prep for the Arlington Futurity, where he would face the far more experienced Buckpasser. Sent off at 2-5 he easily defeated two talented colts in Port Wine and He Jr., winning by six lengths in 1:09 1/5, three-fifths off the track record. Many were shocked that Graustark was bet so heavily considering Port Wine, owned by C.V. Whitney, was unbeaten in four starts at Hollywood Park and had already won the Hollywood Juvenile Championship and Howard Stakes. He Jr. had already won four stakes, two at Arlington, and had been in the money in all 12 of his starts. One of He Jr.’s defeats came at the hands of Fred W. Hooper’s Tinsley, who was also in the Arch Ward field. For Graustark to go off at 2-5 and demolish such talented horses, it came as no surprise when the word freak started to be used frequently.

Unfortunately, shin splints sidelined Graustark for the rest of the year, leaving Buckpasser to clean up most of the remaining 2-year-old stakes.

Both colts headed to Hialeah, where the majority of top horses were stabled for the winter back when the track was in its hey day.

Graustark was the first to show up, once again toying with his opposition to win a six-furlong allowance race by five lengths. An interesting jockey scenario was shaping up with Braulio Baeza, who had been the contract rider for Darby Dan for years and now was riding the majority of top Phipps horses. Here he was the regular rider for the two best young horses in the country.

It was in February that racing fans finally were able to get a good gauge on the merits of Graustark compared to Buckpasser. On Feb 2 Graustark faced his biggest test, squaring off against Buckpasser’s lightning-fast stablemate Impressive in the seven-furlong Bahamas Stakes.

In his three previous starts, Impressive had won the Saratoga Special, finished second to Buckpasser in the Hopeful Stakes, and won his 3-year-old debut, cruising to a 2 3/4-length score in the seven-furlong Hibiscus Stakes.

Despite Impressive’s excellent form and blazing speed, Graustark was sent off as the 1-5 favorite. In all his previous starts, Graustark had dueled for the lead for the first quarter mile before bidding farewell to his opponents. The question was, how would he stand up to the pressure put on him by Impressive, who was virtually impossible to outrun early.

When the gates opened, Graustark hesitated briefly and found himself back in fifth, seven lengths off the pace, with Impressive winging out there all alone by three lengths. Graustark would have to do something he’d never done before and have enough of a closing kick to run down a very dangerous horse loose on the lead.

Baeza moved Graustark up between horses and then swung him to the far outside. Inside the eighth pole, Graustark, still on cruise control, roared past Impressive like he was standing still and easily drew off to win by four lengths before galloping out a full mile.

No one could believe it. Graustark’s performance took on added meaning 12 days later when Buckpasser, now ridden by Bill Shoemaker, made his 3-year-old debut in a seven-furlong allowance race, run as a betless exhibition, and was trounced by Impressive, who won by 4 1/2 lengths in a blazing 1:21 4/5.

If Graustark had one Achilles heel it was unsoundness. Even Baeza said, “He has troubles and they are getting bigger.”

It was one of those minor troubles, a bruised heel, that kept him out of the Everglades and Flamingo Stakes, both won in photos by Buckpasser with Shoemaker aboard. The latter was one of the most talked about and controversial races in years. Despite the Flamingo drawing nine entries, Hialeah decided to make it an exhibition race, which outraged the bettors. The result was the race being dubbed “The Chicken Flamingo.”

In the stretch, the hard-knocking Abe’s Hope charged right on by Buckpasser and opened nearly a two-length advantage. The mighty Buckpasser was about to taste defeat again. But in one of the most remarkable comebacks ever seen, Buckpasser dug deep and somehow found another gear. He came back at Abe’s Hope and in a final desperate lunge stuck his nose in front right on the wire.

Derby fever now reached a feverish pitch, but just as racing fans began to dream about this epic confrontation on the first Saturday in May, Buckpasser suffered a nasty quarter crack that would sideline him for three months.

Graustark now looked to have the Derby at his mercy. It was said he was 10 pounds superior to the other Derby hopefuls. Coming back from a minor setback himself that sidelined him for two months, Graustark was entered in a six-furlong allowance race at Keeneland that, as expected, had no wagering. Baeza kept him two lengths off the pace and then let him loose, and the big liver chestnut just glided away from his opponents and won eased up by four lengths in 1:09 3/5. He kept going past the wire, galloping out the seven furlongs in 1:22 2/5 and pulling up a mile in 1:37 flat.

By now the superlatives for Graustark were coming fast and furious. He became the shortest-priced Derby favorite ever in the Caliente Future Book.

To give an example of the esteem in which Graustark was held as he prepared for the Derby at Keeneland, Tony Alessio of the Caliente Future Book, said, “All my scouts from New York to Chicago to Florida tell me that Graustark may come closer to be being a ‘wonder horse’ than any since Man o’War. He is the hottest thing since Native Dancer and a much higher demand. You’d think from the action that Graustark had wings as well as hoofs.  They tell me he may be the horse of our times.”

Hall of Fame trainer Henry Forrest, who had seen the best over the past 50 years, stated emphatically, “Graustark is the greatest horse I ever laid eyes on.”

Noted Thoroughbred Record turf writer David Alexander said, “Graustark is simply breathtaking the first time you pop your eyeballs at him. When you see him move you seem to hear a symphony resounding in your head, and his stride is like the strophes of a major poet.”

In describing him physically, legendary turf writer Charles Hatton wrote in the Daily Racing Form Racing Manual, “Graustark is taller than long with deer like legs that look like they can carry him to pastures back of the moon. His whole physical and mental organization is that of a born flier, moreover inspires the momentum and fluid action to carry him any reasonable route. He has the supple equipment of a long-distance runner. He is an uncommonly generous horse, exuding speed from every pore.”

Daily Racing Form pedigree expert Leon Rasmussen, said, “On all counts, Graustark has the most magnificent pedigree this corner has ever observed in an American-bred colt.”

One of those who laid eyes on him early in his career was Arlington clocker Jim Milner, who said, “Methinks we shall not see the likes of Graustark again in our lifetime.”

Others called him “Inspiring,” “A true wonder horse,” “A world beater,” and one simply said, “Graustark looks so good it’s frightening.”

His final steppingstone was the Blue Grass Stakes. Gentry began taking heat about the way he was training Graustark, who was now known as “The Big G.” The day before the Blue Grass, Graustark blew out three furlongs in the slop in :33 4/5 and returned lame. It was discovered he had an infected hoof. Gentry blamed it on the blacksmith putting the nail in wrong and announced he would still run Graustark in the Blue Grass. He admitted it was a gamble, but said he had to take the chance if he was going to have Graustark fit enough for the Derby. Galbreath was never one to interfere with his trainer and decided to trust Gentry’s judgment and go along with his decision.

In the Blue Grass, run over a sloppy track, Graustark opened a huge lead, but drifted wide early. Because the colt needed to be tested to get ready for the Derby, Baeza was told by Gentry to let the others close in on him and then ask Graustark for his run at the quarter pole. With Baeza grabbing hold of Graustark as instructed instead of letting him go, Abe’s Hope closed the gap and got a good half-length lead in the stretch before Graustark could regain his mometum. Once he did he came charging back at him, only to fall a nose short. It was his first career defeat. But far worse than the defeat, he came out of the race with a fractured coffin bone in his left front foot.

The injury likely occurred when Graustark was asked to go from a pull to a drive in a matter of a few strides, possibly compounded by the sloppy track and hoof infection the day before. Everyone marveled at the colt’s courage, running the last quarter mile with a fracture. Not only did he battle back and nearly pull it off, he galloped out the full mile and a quarter of the Derby in 2:03 2/5, which may have exacerbated the situation even further. As the chart footnotes read: “Graustark came back with both rundown bandages behind worked well up the leg and off the ankles.”

Just like that, one of the most anticipated Kentucky Derbys in years lost both its superstars. The racing world was crushed. Sports Illustrated took a shot at Gentry in their May 23 issue, publishing an extensive feature on Graustark, with the title, “Boo Made a Boo Boo.”

The Triple Crown became anti-climactic, although we almost had a Triple Crown winner when Kauai King, winner of the Fountain of Youth, Governor’s Gold Cup, and Prince George’s Stakes, captured the Kentucky Derby and Preakness, but was beaten by Amberoid in the Belmont Stakes.

Kauai King was trained by Henry Forrest, who never wavered from his assertion that Graustark was the greatest horse he ever laid eyes on.

Buckpasser, with Braulio Baeza back on him, returned to the races in early June and went on to become one of the greatest horses of all time, winning 25 of his 31 starts, including 15 consecutive victories.

When he set a world record for the mile in 1:32 3/5 in the Arlington Classic, it was his speedy stablemate Impressive who paved the way by blazing fractions of :43 3/5 and 1:06 4/5.

When Baeza was asked to compare Graustark and Buckpasser the following year, he said, “The only way to judge them was at the same stages of their careers last winter at Hialeah. If they met, Graustark would have pulled away from Buckpasser. Of this I am very positive.”

While Graustark was still running, Baeza commented, “What action he has. He is like a cat and does everything so easily. I don’t believe he gets his feet more than an inch off the ground. I’m sure no 3-year-old in the country could beat him. I don’t think any 4-year-old or 5-year-old could beat him.”

Even in his one defeat, Graustark left a lasting impression on David Alexander. “As he went around the first turn, that’s when I really ‘saw’ Graustark,” he said. “I had managed to keep my mouth closed before then, but now it fell open. I say now I have seldom seen a horse whose appearance was more impressive, or whose action was more flawless than that of Graustark.”

Graustark never ran again after the Blue Grass and was retired to Darby Dan, where he had a lucrative career at stud, siring many top-class stakes winners, including several classic winners. His son Prove Out had the distinction of defeating four future Hall of Famers -- Secretariat, Riva Ridge, Forego, and Cougar II -- after being sold and turned over to Allen Jerkens.

One can only speculate what would have happened if both Graustark and Buckpasser had made the Derby or what Graustark would have done to that Derby field had he not been injured in the Blue Grass. Which horse would have gone on to a Hall of Fame career? Most likely both. We will never know.

Most racing fans have little knowledge of the 1966 Triple Crown season, and especially of Graustark, whose magic and mystique have faded with the years. But, oh, what he might have been.

The magnificent Graustark at stud
The magnificent Graustark at stud

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