DEL MAR, Calif. – After Giant’s Causeway took a tough, narrow loss to Tiznow in the 2000 Breeders’ Cup Classic at Churchill Downs, his 31-year-old trainer Aidan O’Brien surely imagined, even if he’d hesitate to admit it now, that before too long he’d win a Classic. One year later, O’Brien saddled his first Breeders’ Cup winner, Johannesburg, who transitioned from European turf racing to American dirt and won the Juvenile. O’Brien has since won 17 more Breeders’ Cup races. He has won the Breeders’ Cup Turf seven times. Every major race in Ireland, his home, has fallen to O’Brien many times over. The spring before Johannesburg triumphed at Belmont Park, O’Brien won his first English Derby. He since has won nine more – 10 Derbies! – and won the Prix de l’Arc de Triomphe twice. O’Brien has sent major race winners to Dubai and Hong Kong. Twenty-four years and 16 attempts after Giant’s Causeway, Aidan O’Brien has not won the Breeders’ Cup Classic. No trainer has run nearly as many Classic horses without winning. Shug McGaughey is 0 for 9, Todd Pletcher 1 for 18. Only three of O’Brien’s finished third or better. Ten were sixth or worse, and one of those, George Washington, catastrophically broke down in front of the Monmouth Park grandstand. :: ON SALE NOW: DRF Breeders' Cup Packages! Get everything you need to win and save 41% off the retail price. Henrythenavigator made a run at victorious Raven’s Pass and finished second in 2008, one of the Breeders’ Cup synthetic years. And there was 2013, Declaration of War third in a three-horse photo finish. Knowledgeable racing people, without hyperbole, call O’Brien a genius, the best horse trainer in the world. His problem with the Classic: The race is run on dirt, and O’Brien trains European grass horses. When he has sent horses good enough to win, they generally failed to carry their form across surfaces. When he sent horses either bred for or competent on dirt, they weren’t good enough – though in Giant’s Causeway’s case, just barely. Sometimes it felt like O’Brien was throwing darts blindfolded: What were Black Minnaloushe and War Decree doing here? Mendelssohn clunked home fifth in 2018. O’Brien hasn’t started a horse in the race since. Until this year. Now comes City of Troy, a 3-year-old colt of modest stature, perhaps the most noteworthy part of his appearance a skunk tail. He’s a fabulous racehorse, a Group 1 winner over seven furlongs and over 12, capable of making the pace or coming from well off it. The people behind him say City of Troy represents their best chance yet at a Breeders’ Cup Classic. O’Brien’s history in the race says they’re at least close to correct. 2000 Breeders’ Cup Classic Giant’s Causeway, 2nd O’Brien began his Classic quest with a horse better bred for dirt than most he’s sent. Giant’s Causeway’s sire, Storm Cat, got plenty of grass horses but was, after all, an American stallion. Giant’s Causeway’s dam, Mariah’s Storm, won a bevy of graded dirt-route stakes. Giant’s Causeway also had immense talent. A Group 1 winner unbeaten in three starts at age 2, he finished second of 27 as the favorite in the 2000 Guineas in May 2000, his only loss in seven starts over good or firm turf. With speed for a mile, as he showed winning the St. James’s Palace and the Sussex, and the fortitude for 1 1/4 miles, demonstrated in the Juddmonte International and the Irish Champion, Giant’s Causeway made the 10th start of his 3-year-old season in the Classic, up for the challenge even at the end of a long campaign. :: Get the inside scoop from the morning workouts with Breeders' Cup Clocker Reports from Mike Welsch and the DRF Clocker Team He had the double misfortune of drawing a bad post, 13 of 13, that led to compromising ground loss, and of running into an excellent winner, Tiznow, who repeated in the 2001 Classic. Giant’s Causeway finished more than three lengths ahead of third-place Captain Steve, who went on to win the Dubai World Cup the following March. Everything went to plan – except winning. 2001 Classic Galileo, 6th Black Minnaloushe, 12th Galileo sired City of Troy’s dam, Together Forever, as well as a cascade of Group 1 winners. He is one of the greatest stallions of recent vintage, and part of the pantheon of great horses O’Brien has trained. Among the six victories he notched to begin his career: the Epsom Derby, the Irish Derby, the grand King George VI and Queen Elizabeth, where he beat older rivals in first try. Galileo tasted his first defeat in the Irish Champion Stakes, losing by a head in his first top-level race over 1 1/4 miles. Galileo was a 1 1/2-mile horse, which alone made the Classic an iffy proposition. Worse, his turf form failed to translate to dirt. He never reached contention in the Classic. Black Minnaloushe? He ran like the 50-1 shot he was. 2002 Classic Hawk Wing, 7th No Giant’s Causeway or Galileo but a very good horse, perhaps hitting his peak at a distance shorter than 1 1/4 miles, though he won a Group 1 at the trip. Hawk Wing had turned in two strong performances three weeks apart in September before turning in a weak one a month later at Arlington Park. The horse couldn’t handle dirt at all and lost by 17 1/2 lengths. 2003 Classic Hold that Tiger, 5th A new approach for a fourth Classic attempt! Hold That Tiger, like Giant’s Causeway, was by Storm Cat, and his dam, Beware of the Cat, produced the winner of the 1996 Belmont Stakes, Editor’s Note. He had run to that dirt-leaning pedigree in the 2002 Breeders’ Cup Juvenile, finishing third, and after three modest showings on English turf courses in 2003, O’Brien focused on American dirt. He sent Hold That Tiger to prep for the Classic in the Woodward Stakes at Belmont. Hold That Tiger lost by four lengths. He ran his race in the Classic. It wasn’t good enough. 2005 Classic Oratorio, 11th At least Oratorio excelled at 1 1/4 miles. After tinkering through his 3-year-old campaign, adding blinkers for one start, O’Brien finally got top performances out of Oratorio winning two key 10-furlong contests, the Eclipse and the Irish Champion. :: Get Breeders' Cup Betting Strategies from Brad Free and David Aragona for exclusive wager recommendations and play the races with confidence! But consider that Oratorio made the 15th start of a two-season career in the Classic at Belmont. The race came onto connections’ radar only after the horse blossomed the second part of his 2005 season. Also, the pedigree, by Danehill out of a Vaguely Noble mare, turf over turf. Oratorio went off to a modest career at stud after beating two of 12 rivals at Belmont. 2006, 2007 Classics George Washington, 6th, DNF Another son of Danehill. At least this one was out of a mare by the American horse Alysheba. If dirt felt like a longshot, so did 1 1/4 miles. George Washington won all his races over one mile or shorter and hadn’t even gone beyond a mile when he finished a fading sixth as a 3-year-old at Churchill Downs in 2006. The less said about the tragic end of the 2007 Classic, the better, but in the end, George, despite his name, was not a horse for America. 2008 Classic Duke of Marmalade, 9th Henrythenavigator, 2nd Does this even count? Santa Anita hosted this Breeders’ Cup during its synthetic-surface era, and synthetics play more like turf than dirt. No coincidence: English and Irish horses filled the first two Classic places. Duke of Marmalade had raced 20 days earlier in the Prix de l’Arc de Triomphe. Henrythenavigator was a miler hoping to stretch to an American 1 1/4 miles. He’d have fared worse on dirt. 2009 Classic Rip Van Winkle, 10th Year two of synthetic Breeders’ Cups. Many judged Rip Van Winkle the leading threat to the great Zenyatta. Not so much. Good horse, Rip Van Winkle, who had a bad day. 2011 Classic So You Think, 5th An Australian star during his early career, So You Think proved equally capable in Europe, ending his career with an amazing 10 Group 1 wins in two hemispheres. He began racing a full 2 1/2 years before he tried the Classic at Churchill Downs, his 20th start, hardly the culmination of a plan, merely a hope that a horse bred entirely for turf might make it happen on dirt. A respectable sixth in a soft renewal. 2013 Classic Declaration of War, 3rd Almost. A horse that came closer, beaten a head, even than Giant’s Causeway, but with a completely different background. No more than a Group 3 winner at the end of his sophomore campaign, Declaration of War flowered as a 4-year-old, though not quite at the level of O’Brien’s very best. Interesting note: Declaration of War won the Juddmonte International over 1 5/16 miles in August and didn’t start again until the Breeders’ Cup – just like City of Troy. Unlike in other seasons, the Classic had been the target. O’Brien just missed hitting it. 2015 Classic Gleneagles, 8th Eighth, yes, but only eight started. A turf miler by Galileo, Gleneagles raced two weeks before the Classic in the Queen Elizabeth at Ascot. C’mon – nothing more than a Hail Mary, this one. :: BREEDERS’ CUP CLASSIC: See DRF’s special section with top contenders, odds, comments, news, and more 2017 Classic Churchill, 7th War Decree, 9th A Galileo turf miler, anyone? Takers? No? Churchill won the English and Irish Guineas in late spring but faded in late summer and fall. Here, again, came a horse who had raced two weeks earlier at Ascot, Gleneagles all over again, beaten a mile. No idea why War Decree, the least talented horse O’Brien ever ran in the Classic, went to Del Mar, 2018 Classic Mendelssohn, 5th Another dirt horse, and another dirt horse not good enough for the Classic. Mendelssohn, last of 20 in the Kentucky Derby, already had four American dirt races behind him when he showed up at Churchill for the Classic, finishing a respectable fifth. Present day Since Giant’s Causeway, O’Brien and Coolmore never had gone more than two years without a Classic runner. Now it has been six. Giving up? No. Retrenching and planning? Yes. Asked Tuesday morning if he went back to watch his previous Classic runners, O’Brien said, “Every one! Hundreds of times!” And might only have exaggerated mildly. Coolmore stands City of Troy’s sire, the Triple Crown winner Justify, at Ashford Stud in Kentucky. M.V. Magnier, a Coolmore principal, bought Together Forever in 2013 for about $736,000. Her four other foals to race have ranged from okay to good, but nothing like this. City of Troy, O’Brien said, looked different from the moment he took up training. His speed, his sire – this colt, the camp decided, could be The One. Whatever goes down Saturday, City of Troy already has compiled an epic record, winner of Europe’s most important 2-year-old race, the Dewhurst, and a strong hero of the 1 1/2-mile Derby at Epsom. City of Troy failed to show brilliance but still beat older horses in the Eclipse, then ran his best race yet in the International, where he set a course record, albeit over very fast ground. As with Declaration of War, that was it – no more real racing until America. One disappointment, a grave one, an absolute dud at odds of 3-5 in the 2000 Guineas. Antsy in the stalls, City of Troy flew into the race under the great Ryan Moore, then backed quickly out of it after contesting a furious tempo. O’Brien insisted particular and correctable miscalculations had produced the grim ninth-place finish. It’s not just pedigree and stride mechanics separating American from European racehorses. Horses learn different lessons on the two sides of the Atlantic, Europeans to leave the gate and melt into their riders’ hands, to switch off and run as slow as necessary during the early stages, gradually accelerating to a crescendo. American dirt racing unfolds fast early, slow late, an exercise in high speed and deceleration: No coincidence that the leading Classic trainer, Bob Baffert, first trained Quarter Horses. City of Troy’s preparations for Saturday’s start began as a 2-year-old, trained from early days to adapt to American race flows. It has not been straightforward. The colt pulled hard as a 2-year-old and required a stern bit for his rider to exert appropriate control. He improved, the bit was changed to a lighter version – and then City of Troy ran off in the Guineas. Back to the drawing board. O’Brien changed bits again for the Derby – and tactics. City of Troy needed a lesson in going slow early, not fast: He won at Epsom from the back of the pack. Yet another bit was deployed for the Eclipse, another still for the International, but by then, City of Troy had come back to hand, and now it was time to let him use his speed again, as the Classic would require. The horse that came from 14th in the Derby over 1 1/2 miles led from start to finish going 1 5/16 miles at York. :: Bet the races with a $200 First Deposit Match + FREE All Access PPs! Join DRF Bets. No idle time these last 2 1/2 months. In mid-September, O’Brien simulated a race, sending City of Troy and four workmates to breeze over the synthetic surface at Southwell Racecourse in England. O’Brien wanted to focus on the early stages of the work, for the workmates to run as fast, or faster, than an American dirt pace and force City of Troy to adapt. The colt went through another serious workout, more recently, at O’Brien’s training yard in Ireland. All has gone to plan. City of Troy presumably bears the name not of minor municipalities in Ohio or New York, but of Ancient Troy. A name from classical antiquity for a horse who won Europe’s most important classic race, the Derby at Epsom, and now has come to Del Mar for another Classic. One of the least imposing horses among a dozen O’Briens that walked out to the Del Mar track Tuesday morning, City of Troy never would catch the eye of a casual observer. There’s much more to him than meets the eye. His innate ability, yes, but months and months of planning. Attention to every detail. Bringing to bear a litany of Classic losses. Maybe it works, maybe it doesn’t. This is O’Brien’s best chance yet. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.