One Loss Wonders

They’re the races that pain us to watch again, the races that many devoted fans refuse to re-watch, the races that broke our hearts. Whether it was a demolishment or a photo finish, the sole defeat of an otherwise undefeated horse is always a sore spot for loving fans of such a Thoroughbred. We’ve had our fair share of near-undefeated horses recently, but there have been other horses of that sort in the past as well. One thing about these horses is certain: they were among the most popular racehorses of all-time. Here is a look at some of the “One Loss Wonders” of racing’s past:

Zenyatta: The great mare did not begin her career until Thanksgiving Day of her three-year-old career and after winning a maiden and an allowance, Zenyatta went into 2008 with two wins in just as many starts. She posted victory after victory, winning four grade ones that year, including the Breeders’ Cup Ladies’ Classic (GI). A year later, the “Dancing Queen” captured yet another four grade ones, becoming the only female racehorse in history to win the prestigious Breeders’ Cup Classic (GI).

Zenyatta
Photo by Terri Cage

In 2010, Zenyatta was brought out of a very brief retirement to have one more year at the races. She continued to reel off wins, earning five more grade one triumphs as she ran her record to nineteen-for-nineteen, which, at the time, was tied with Peppers Pride for number of consecutive wins in modern-day North American racing. Her final start was the Breeders’ Cup Classic (GI), a race full of possibilities for the great mare. A win would not only secure her immortality for becoming the only horse to go undefeated in twenty career starts, but she would also be just the second horse to win three times at the Breeders’ Cup – Goldikova had amassed that achievement earlier in the day – and also only the second racehorse to ever win the Classic twice.

Of the six losses discussed in this blog, this was the only one I was present for. That, combined with the fact that Zenyatta is my favorite racehorse of all-time, leads the loss to hit home for me. Zenyatta broke slowly from the gate at Churchill Downs – normal for her, but more detrimental than any other time she’d come out of the starting gate slowly. She never appeared comfortable as she galloped over a surface over which she’d never raced, seeming to dislike the kickback that flew towards her. Zenyatta made a valiant rally under Hall of Fame rider Mike Smith, maneuvering traffic and charging like a freight train on the outside to miss defeating Blame by an official margin of a head, her head bobbing past him just after they flashed under the wire. It was certainly a race for the ages, but it was also one of the most heartrending races of all-time. It was a race that sent me rushing out of the grandstand before anyone could stop me, leaving me absolutely heartbroken. All along, I knew I wasn’t the only one left with a broken heart following the race.

Big Brown: He’d only raced three times going into the Kentucky Derby (GI), but each of those races – which resulted in wins – were monster performances. He’d won those three races by a combined winning margin of 29 lengths. As the favorite in the Derby, Big Brown cruised to a 4 ¾-length victory. With his impressive victory in the Derby, hopes were high as he continued on to the second leg of the Triple Crown, the Preakness Stakes (GI). Yet again, the colt turned in a fantastic performance, crossing the wire 5 ¼ lengths ahead. The confidence invested in Big Brown as he proceeded to the Belmont Stakes (GI) in pursuit of becoming the twelfth Triple Crown winner soared. The racing world was nearly certain that Big Brown was the one.

However, nothing seemed to go right at the Belmont. Big Brown had recently suffered one of his infamous quarter cracks, though his connections assured the media the colt was fine. On race day, the colt was uneasy in the detention barn and as the field warmed up for the twelve-furlong race, the colt was lathered in sweat, clearly affected by the heat and humidity. The race was over from the start. His shoe was partly dislodged from his right hind hoof at the beginning of the race, leaving it only partially on as he embarked on the twelve-furlong journey – something that surely was uncomfortable for the colt. Big Brown appeared rather rank throughout the race, though he eventually seemed to find the perfect stalking position. But the normal Big Brown did not show up. Fans were used to seeing the colt loom on the outside on the far turn as jockey Kent Desormeaux sat as still as a statue prior to opening up on the field. Rather, Desormeaux began urging the colt with a half-mile remaining, getting no response from the Derby and Preakness winner. Then came the worst part of the race: Big Brown was eased.

The colt emerged from the race sound, leaving fans devastated by his abnormal, shocking loss. But he returned later that year to win his last two starts, the Haskell Invitational Stakes (GI) and the Monmouth Stakes in New Jersey. He was expected to compete in the Breeders’ Cup Classic (GI) in the fall at Santa Anita, but a hoof injury forced his retirement. Despite his short career, unpopular connections, and distressing Belmont loss, Big Brown had rallied fans to become one of the most popular racehorses of the past decade.

Smarty Jones
Photo by Terri Cage

Smarty Jones: Despite his undefeated record that included a win in the Arkansas Derby (GII), Smarty Jones had plenty of doubters when he went to post in the Kentucky Derby. Over a very sloppy track, Smarty Jones settled off the pace set by Lion Heart before pouncing on the leader as the two turned for home. He hooked up with Lion Heart at the top of the stretch before looking the horse in the eye and galloping away to a 2 ¾-length victory. In the Preakness, Smarty blew his fans away by thundering to a dazzling 11 ½-length triumph, the largest winning margin in the history of the race.

It seemed as if we would finally see the first Triple Crown winner in twenty-six years. As the Belmont approached, fans were eager for Smarty Jones’ bid for the Triple Crown. As the horses turned for home and continued down the stretch at Belmont, Smarty seemed to have the win. But Birdstone caught up to the determined and exhausted colt, sweeping past him to win by just one length.

Smarty Jones was retired months after the Belmont, which ended up being his last race, due to bone bruises. Though his loss was heartbreaking, it displayed how elusive the title of Triple Crown winner is, how much love a nation can share for a horse, and that things can’t always be perfect. It also made it evident that Smarty Jones was a horse that never gave up.

Brigadier Gerard: As a juvenile, the British Thoroughbred won each of his four starts. He made his initial sophomore start in the first leg of the English Triple Crown, the 2,000 Guineas Stakes, winning the prestigious classic by three lengths. He added five more wins to his credit in just as many starts, dominating prestigious races throughout Great Britain. By the end of his three-year-old career, Brigadier had run his perfect record to ten races. As a four-year-old, Brigadier kicked off his final racing campaign with victories in five renowned races. The bay colt appeared unbeatable.

But when he started in the Benson & Hedges Gold Cup in his sixth start as a four-year-old, he was going ten furlongs – a distance he had won at before, but not one he really had an affinity for. Facing the Epsom Derby victor, Roberto, Brigadier Gerard was left behind as the champion colt led the field throughout, drawing off to an easy win that left Brigadier Gerard with the taste of defeat for the first and only time of his career.

Brigadier Gerard, however, returned to his winning ways, capturing two more renowned races – the Queen Elizabeth II Stakes and the Champion Stakes – while forming a new course record along the way. Despite his loss, he garnered the title of British Horse of the Year. Though he had a blemish in his record from his sole defeat, Brigadier Gerard retired with a nearly flawless record and is remembered as one of the best racehorses Britain has ever seen.

Majestic Prince: The son of Raise a Native entered the Kentucky Derby with an undefeated record on the line, being sent off as the favorite despite a deep field that included Arts and Letters and Top Knight. Down the stretch, Majestic Prince battled Arts and Letters in a thrilling stretch duel prior to prevailing by a neck. The rivals duked it out yet again in the Preakness when Arts and Letters loomed on Majestic Prince’s outside in the stretch. The Derby winner had enough to hold off the great Arts and Letters by a head to score his ninth straight victory.

When Majestic Prince displayed a tendon issue following the Preakness, it was debated whether or not he would go for the Triple Crown in the Belmont Stakes. But the decision was made that the dual classic victor would go for the feat that hadn’t been accomplished in twenty-one years despite not being at his best. It cost him. Majestic Prince was defeated by his rival Arts and Letters by 5 ½ lengths in the Belmont to lose not only the Triple Crown, but the first and last race he would ever lose.

The popular colt never raced again after the Belmont, in which he joined a large assembly of horses that won the Kentucky Derby and Preakness but did not succeed in the Belmont. Ironically, a similar situation played out in this year's Triple Crown when I'll Have Another was diagnosed with a tendon issue prior to what would have been a Triple Crown attempt in the Belmont. However, unlike Majestic Prince, I'll Have Another was scratched.   

Native Dancer: As a two-year-old, Native Dancer captured all nine of his races and even set a world record time for six and one-half furlongs while doing so. He was honored as 1952 Champion Two-Year-Old Male as a result of his spectacular juvenile campaign. Following wins in the Gotham Stakes and Wood Memorial, Native Dancer went to post in the greatest race of the year and one he was expected to win, the Kentucky Derby.

But following a bit of a slow break, Native Dancer found himself behind a wall of horses as the field galloped into the clubhouse turn. On that curve, the Dancer was interfered with and forced to check, but found a good position after the incident. But later in the race, Native Dancer faced yet another wall of horses. After maneuvering traffic, Native Dancer set his sights on the leader, Dark Star, and despite rallying, he finished a head behind Dark Star to post his only loss in his career and a defeat in the most important race of the year.

Native Dancer’s loss hung like a dark, sad cloud over racing fans. This horse had been expected to win the Triple Crown, but by losing the Derby, he had not shot at doing so. Though his wins in the Preakness and Belmont were joyous to racing fans, they were also bittersweet, as the Dancer was just a scant head away from being a Triple Crown victor. After the Derby, Native Dancer never lost again, capturing nine more victories. His Derby loss remains a heartbreaker for his adoring fans, but what he couldn’t accomplish on the track, he made up for in the breeding shed, siring the winner of the 1966 Kentucky Derby. In fact, nineteen Derby victors have descended from the Native Dancer sire line.

Man O’ War: Within a span of about two months, Man O’ War won all six of his initial six starts, many of which were won by substantial margins. He was viewed as the top juvenile colt in the nation, having won stakes at four different tracks in New York in impressive fashion. In his second start at Saratoga, the chestnut colt went to post in the Sanford.

Also in the field was a colt named Upset, a horse Man O’ War had faced before, even giving fifteen pounds to the son of Whisk Broom. Yet again, Man O’ War carried fifteen more pounds than the chestnut with three white stockings. Many accounts say that Man O’ War was facing the opposite way when the race began, giving him a huge disadvantage. Johnny Loftus guided the horse throughout the race, but Man O’ War became boxed in with just a furlong left of the race. The young jockey angled the brilliant colt to the outside and the two rallied, but Man O’ War came up a half-length short of Upset to record the only loss of his career.

Man O’ War’s defeat was a crushing loss, but the colt rebounded and never lost again, capturing many prestigious races, including the Preakness Stakes, Belmont Stakes, Travers Stakes, and Jockey Club Gold Cup. The son of Fair Play is still considered by many to be the greatest racehorse of all-time. He may not have been undefeated, but his loss left not only an everlasting effect on horse racing, but on sports in general. The term upset, used when the favorite – or the competitor/team expected to win – is defeated by one expected to lose, derived from the name of the single horse to ever defeat the great Man O’ War.

Sysonby: This horse won his first four starts with breathtaking ease. In fact, he’d won them by a combined twenty-two lengths. He was deemed unbeatable, and certainly the best juvenile in the country.

Everyone expected for the bay colt to win his fifth start, the 1904 Futurity Stakes at Sheepshead Bay, in spite of having to carry 127 pounds as the highweight in a deep field. But Sysonby was defeated by a substantial margin as the eventual champion filly Artful galloped to victory. Many were stunned that Sysonby had been defeated, but a groom that worked for his owner, James Keene, confessed that he had drugged the colt as part of a bribe.

Sysonby’s sound but understood, valiant defeat remained the only blemish on his record as the bay horse went on to win the rest of his starts, though one victory came in a dead heat in the Metropolitan Handicap. By the end of his career, Sysonby had won fourteen of fifteen career starts. Unfortunately, the colt’s career came to a tragic end when he died at the age of four due to variola. His popularity was evident when the horse was buried, as more than four thousand people attended the event, bidding their farewells to the brilliant horse.

The losses of these horses may have left their fans feeling heartbroken and crushed, but for many of them, it also solidified their greatness. It proved that not even the best are perfect, and even without perfect racing records, these horses were flawless in their fans’ hearts and minds. 


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