There are certainly numerous reasons to remember the racing career of Ferdinand.

He was the Horse of the Year and the champion handicap horse of 1987.

In that year’s Breeders’ Cup Classic, he defeated Kentucky Derby and Preakness winner Alysheba by a scant nostril in one of the most exciting editions of America’s richest race.

He won only eight of 29 starts in his career, but still managed to retire in 1988 with earnings of $3,777,978, which at that time ranked him fifth on the all-time list.

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Yet what many people will fondly recall about Ferdinand centers not just on his victory in the 1986 Kentucky Derby, but also the Hall of Famers he ushered into the famed winner’s circle at Churchill Downs on the first Saturday in May.

Amazingly, through his first 36 years as a trainer, Charlie Whittingham won just about every major race on the West Coast, but never a single Triple Crown race.

That all changed on a bright, glorious May afternoon in Louisville when Ferdinand shot through an opening along the rail and gave Whittingham his first Kentucky Derby victory at the robust age of 73.

He was ridden that day by none other than 54-year-old Bill Shoemaker, whose masterful ride on Ferdinand accounted for the fourth and final Kentucky Derby victory of his legendary career – but his first since 1965.

It was a magnificent and completely unforgettable day for racing’s “Sunshine Boys” as they became the oldest trainer and jockey to win the Kentucky Derby, and it was a strapping, chestnut son of Nijinsky II named Ferdinand who made it all possible.

A homebred out of the Double Jay mare Banja Luka raced by Howard Keck and his wife, Elizabeth “Libby” Keck, Ferdinand debuted on Sept. 8, 1985 at Del Mar and did little to stamp himself as a runner with a bright future. He languished behind at the rear of the field throughout the six-furlong maiden race and wound up eighth, beaten by 11 ½ lengths with Shoemaker in the saddle.

That initial start, however, proved to be quite educational as Ferdinand rallied to finish third in his next race and then finished second by a nose when he stretched out to a mile for an Oct. 20 start at Santa Abita.

In his next try, the late-running Ferdinand rolled to an easy 2 ¼-length maiden victory as a 2-5 favorite and Whittingham wasted little time in upping the ante.

He entered Ferdinand in the Grade 1 Hollywood Futurity where Ferdinand was dismissed as a 34-1 outsider. Whittingham’s colt got off to a slow start, but it really didn’t matter as Snow Chief romped by 6 ½ lengths in the mile stakes.

Ferdinand, for his part, showed that he might have a nice future in two-turn stakes at three by rallying for third and missing the place spot by a nose.

In his first three starts at three, Ferdinand continued to progress by finishing second in the Los Feliz, winning the Santa Catalina, and grabbing second in the Grade 2 San Rafael. Yet he still had an irritating habit of losing his focus once he grabbed the lead. It happened in the Los Feliz when he forged to a length and a half lead at the eighth pole before losing to Badger Land by a head, and then in the San Rafael when he squandered a two-length lead with a furlong to go and lost by a half-length to Variety Road.

“When Ferdinand gets to the lead, he pricks his ears and then loafs,” Whittingham said in an interview with the Sun-Sentinel. “He should get over that with more racing. If he ever does get over it, he'll be awesome.”

FERDINAND LATER IN HIS CAREER WINNING THE BREEDERS' CUP CLASSIC

Photo courtesy of Blood-Horse/Anne M. Eberhardt

Loafing was the least of Ferdinand’s problems in his rematch with Snow Chief in the Santa Anita Derby. The Kentucky Derby favorite took the lead at the start and kicked into high gear in the stretch, romping home by six lengths as a 3-10 favorite.

Ferdinand never fired on a wet track that was labeled fast and checked in third, seven lengths behind the victorious Snow Chief.

“He was slipping all over the place,” Whittingham said.

Given his 26-year absence at the Kentucky Derby, it seemed unlikely that Whittingham would head to Churchill Downs with Ferdinand. In previous years, five of his horses finished second in the Santa Anita Derby but, for one reason or another, none of them ran in the Derby.

At that point, “The Bald Eagle” had just two Kentucky Derby starts to his credit. The first was Gone Fishin’, who finished eighth in the 1958 Derby, and then Divine Comedy, who was ninth in the 1960 Derby  when Whittingham was just 47 years old.

That lengthy hiatus was a testament to Whittingham’s philosophy that “there's no use going to the Kentucky Derby unless you've got a top horse.”

“It won't kill me if I don't win again,” Whittingham told the Los Angeles Times. “I haven't done it yet and I'm still breathing. Of course, it'd be a different story if I was from Kentucky. I'd probably have shot myself by now.”

So when Whittingham elected to send Ferdinand to Louisville, a rather loud message was being delivered – even if few were listening.

Though Whittingham sharpened Ferdinand’s speed with a sparkling 58 3/5 seconds, five-furlong workout during Derby week, getting past his career record of two wins in nine starts was difficult. Ferdinand was pegged at a morning-line price of 20-1 when he drew the rail and when the starting gates opened he was 17-1.

Drawing the tricky rail post seemed an added complication for Shoemaker, who was in the waning years of his illustrious career. Though he owned the sport’s record for career wins at the time, he registered a mere 80 wins in 1985.

In 1986, at the age of 54, his glory days were behind him.

Yet if there was an indication of what was to come in the 112th Derby, it could be found not at a horse race track, but at Augusta, where a month earlier Jack Nicklaus, at the age of 46, captured the Masters to become the second-oldest winner of a Grand Slam event.  

“This might be the year for old-timers,” Shoemaker told the Los Angeles Times before the Kentucky Derby. “If Nicklaus [at 46] can win the Masters, I can win the Derby.”

Winning the Derby seemed far-fetched when Ferdinand was bumped hard while passing the stands the first time, falling back to last as the field of 16 headed into the first turn. After the opening half-mile, he trailed by 24 lengths.

“It’s always tight coming out of the one post,” Shoemaker said, “and I got pinched back further than I wanted to be. I had to pull the horse back. He was as close as he could get to the rail without going over, then he kind of checked himself. He knew he was close.”

While Shoemaker had his struggles at the back of the pack, up front he received considerable help.

Groovy, who would become the champion sprinter of 1987, set a blistering pace, covering the first half-mile in 45 1/5 and matching the fastest first four furlongs in Derby history. Snow Chief, the 2.10-to-1 favorite, was fourth at that point, just three lengths behind a pace that could that could not be sustained.

While Snow Chief took the lead midway on the final turn, the heavy lifting on the front end soon caught up to him and he had nothing left for the final furlongs.

A wave of pursuers, led by 5-2 second choice Badger Land, Broad Brush and Bold Arrangement swallowed him up and battled for the lead at the top of the stretch.

Behind them, after such a miserable start, Shoemaker and Ferdinand were enjoying a textbook journey, surging past rivals on the turn while moving four paths wide.

Fifth at the quarter pole, Shoemaker had a line of horses in front of him and plenty of horse underneath him. He could have swung wide, but in one of the best moves of his storied career, he darted Ferdinand toward a small hole along the inside. Ferdinand took over from there, bulling through and accelerating brilliantly as his rivals drifted out a bit to give him a clear path to the finish line.

Ferdinand quickly grabbed a length lead at the eighth pole and this time there was no loafing. The chestnut colt widened his lead in the final furlong, crossing the wire 2 ¼ lengths ahead of Bold Arrangement with Broad Brush third.

“This Derby win was the best,” Shoemaker said. “I had tears in my eyes when I came back. I never felt more emotional after a race.”

After filling the biggest hole in a peerless training resume, Whittingham expressed some satisfaction in winning the race strangers most often mention when they learn he trains horses for a living.

“The Kentucky Derby is probably the most important race. It took me 26 years to get here. I said I wouldn’t come unless I had a good horse and we have one now,” Whittingham said. “I don’t know how Bill got through the whole way, but somehow he made it. The man up there was looking out for ‘The Sunshine Boys,’ I guess.”

The heartwarming victory Ferdinand gave a deserving spotlight to two of the sport’s greatest stars and helped foster a huge wave interest in the Preakness.  

A year earlier, the Triple Crown was dealt a staggering blow when 1985 Kentucky Derby winner Spend a Buck skipped the Preakness to chase a $2-million bonus tied to the Jersey Derby at Garden State.

This time, all of the major players headed to Pimlico for an encore in Baltimore, though the betting public had some doubts over Ferdinand’s ability to duplicate his Derby victory. Badger Land, running in an entry with Clear Choice, was sent off a 9-5 favorite, with Snow Chief next at 5-2 and Ferdinand 3-1.

In the Preakness, Groovy again set the pace but the fractions were a more realistic 47 2/5 and 1:11, and Snow Chief was a far different horse than the one that faded to 11th in the Derby.

After pressing Groovy for lead, Snow Chief rocketed to the lead turning for home and coasted to a four-length victory over Ferdinand, who rallied from sixth in the field of seven to take second.

“He just didn’t get a hold of the track here like he did in Kentucky,” Shoemaker said. “But that’s not an excuse. [Snow Chief] just ran his race today. It’s disappointing not to win the Triple Crown, but that’s racing. I’m not going to cry about it.”

Rather than race at the mile and a half distance of the Belmont Stakes, Snow Chief opted for the Jersey Derby, which he won by two lengths over Mogambo.

Ferdinand, meanwhile, stayed on the Triple Crown trail and headed to New York for what turned out to be a race for “the ages.”

Three of the favorites in the race were Ferdinand, trained by the 73-year-old Whittingham, Johns Treasure, trained by 79-year-old Walter Kelley, and Danzig Connection, sent out by 72-year-old Woody Stephens.

Together the trio had 174 years of racing experience and more than 700 stakes wins, but what Stephens had going for him that the other two didn’t was four straight wins in the Belmont.

In the end, a sloppy track and Stephens’ Joe DiMaggio-like streak were too much for Ferdinand to overcome as Danzig Connection gave Stephens a still-unrivaled five straight Belmont and Johns Treasure beat Ferdinand by a neck to take second.

“He ran good, but not good enough,” Shoemaker said about the Derby winner’s third-place finish. “He handled the track pretty good but he just got a little tired. I thought in the stretch he had a chance but then I saw I had asked my horse to run and [jockey Chris McCarron] hadn’t done that yet with [Danzig Connection].”

The Belmont proved to be Ferdinand’s last race for more than six months and his comeback accounted for one of the most impressive performances of his career. Entered in the Grade 2 Malibu on Dec 26 at Santa Anita, Ferdinand met up with Snow Chief at a seven-furlong distance that seemed ideally suited for the Preakness winner.

Ninth after the opening quarter mile, Ferdinand closed strongly in the stretch and collared Snow Chief in the final sixteenth to defeat his rival by a length and a quarter.

Though the Malibu gave Ferdinand a split of four 1986 meetings with Snow Chief, Eclipse Award voters gave the nod to Snow Chief and named him as the year’s champion 3-year-old male.

FERDINAND IN THE MALIBU STAKES

Photo courtesy of Blood-Horse/Four Footed Photos

Their rivalry continued at four, starting with the San Fernando, where Snow Chief was third and Ferdinand fourth behind the victorious Variety Road.

After Snow Chief beat Ferdinand by a nose in the Grade 1 Strub at Santa Anita, they met again in the Grade 1 Santa Anita Handicap as Ferdinand lost by a nose to Broad Brush while Snow Chief checked in fifth.

Their final meeting came in June in the Californian when Snow Chief finished third in the final start of his career and Ferdinand didn’t fire and wound up fifth.

Free of Snow Chief, Ferdinand reeled off consecutive wins in the Hollywood Gold Cup, Cabrillo Handicap, and Goodwood Handicap to arrive at the Breeders’ Cup as an even-money favorite in the $3 million Classic.

The 7-2 second choice was 1987 Kentucky Derby-Preakness winner Alysheba and the matchup of the two most recent Kentucky Derby winners lived up to its lofty expectations. Engaging in a fierce stretch duel, Ferdinand grabbed a short lead in the final yards, only to have Alysheba draw even with him in the last stride.

The finish was so tight that as Shoemaker and McCarron on Alysheba galloped out past the wire the two jockeys joked about a private “saver” wager as insurance to ease the sting of a narrow defeat.  

When the numbers flashed on the toteboard, Ferdinand was declared the winner by a nose and everything was in place for him to be named Horse of the Year and the champion older male.

“This horse has a tendency to ease himself up,” Shoemaker said, “but today he saw just enough of Alysheba coming to get the job done.”

The Kecks kept Ferdinand in training at five, but he failed to win in six starts, including runner-up finishes behind Alysheba in both the Santa Anita Handicap and San Bernardino.

His final start was the 1988 Goodwood when he came home fifth as an 8-5 favorite.

Ferdinand finished with a slate of eight wins, nine seconds, and six thirds from his 29 starts during four seasons of racing.

It wasn’t a record worthy of a spot in the Hall of Fame, but in the end he achieved a different kind of fame. After all, he was the horse who gave Charlie Whittingham his first Kentucky Derby win and proved that an “Old Shoe” could still fit quite nicely on the back of a champion.

Note: This story was originally published in April 2016 and has been updated.

Fun Facts

• Ferdinand’s three Triple Crown starts were the only time he raced outside of California.
• Ferdinand was ridden in his maiden win by Wesley Ward, who has become a four-time Breeders’ Cup-winning trainer.
• Ferdinand was the first Kentucky Derby winner to win the Breeders’ Cup Classic.
• Whittingham won his second Kentucky Derby in 1989 with Sunday Silence.
• Ferdinand’s win in the 1987 Classic accounted for Shoemaker’s lone Breeders Cup victory in 14 mounts.
• Ferdinand was Whittingham’s first Breeders’ Cup triumph and along with Sunday Silence (1989 Classic) was one of his two BC winners in 24 starts.
• Whittingham remained the oldest trainer to win the Kentucky Derby until 2014 when 77-year-old Art Sherman won with California Chrome.
• Howard Keck also owned the auto racing team that won the Indianapolis 500 in 1953 and 1954.
• Ferdinand was originally retired to Claiborne Farm in Kentucky, where he was foaled, but then was sold to Japanese interests in 1994. In 2003, it was reported in BloodHorse that the 1986 Derby winner had died in a Japanese slaughterhouse. The outrage over Ferdinand’s horrific death inspired horsemen to lobby for laws that have outlawed the slaughter of horses in the United States and spawned the creation of measures such as the Ferdinand Fee, which raises money to pay for rescue programs and re-training of Thoroughbreds, and an agreement between the Japan Racing Association and the Old Friends retirement farm to repatriate American horses whose careers at stud in Japan have ended.