In two decades since his first victory with Galileo in 2001, Aidan O’Brien has made history at the Derby at Epsom, where his career total of eight victories is an all-time record.
They can’t all have been world beaters – and in fact, they weren’t, though some of them were pretty good. Here, ahead of Bolshoi Ballet’s bid to become O’Brien’s ninth Derby winner on Saturday, Nicholas Godfrey ranks the previous eight to have reached Federico Tesio’s celebrated “piece of wood” in front of their rivals.
1. Galileo (2001)
Sire: Sadler’s Wells
Jockey: Mick Kinane
Starting odds: 11/4 joint favourite
Best Racing Post Rating 132; Derby RPR 127
Before he became the modern era’s breed-shaping stallion, legendary sire Galileo was an outstanding racehorse, perhaps the greatest ever trained by Aidan O’Brien.
Making his G1 debut after a straightforward victory in the Derrinstown Stud Derby Trial, the exalted son of Sadler’s Wells produced a magnificent performance at Epsom, travelling easily throughout before quickening away to beat to beat 2000 Guineas winner Golan by 3½ lengths in what was the second-fastest time in history. Interestingly, given his stable’s subsequent penchant for block entries – usually via multiple sons of Galileo – he was the sole Ballydoyle runner that year.
He went on to extend his unbeaten record to six with a lap of honour at the Curragh and then a memorable King George victory over arch-rival Fantastic Light before that horse lowered his colours in another fierce contest for the Irish Champion Stakes.
Retired after a fruitless effort on dirt at the Breeders’ Cup, he was to go on to even greater heights in the breeding shed, where five of his progeny (so far) have emulated his Derby success.
2. High Chaparral (2002)
Sire: Sadler’s Wells
Jockey: Johnny Murtagh
Odds: 7/2
Best RPR 130; Derby RPR 130
Talented, tough and resolute, High Chaparral was a top-class middle-distance performer who recorded G1 success over each of his three seasons before being retired with a formidable career record of ten wins from 13 starts, among them a pair of Breeders’ Cup Turfs (one in a dead-heat on his final start as a 4-year-old).
Although he spent the winter as Ballydoyle’s foremost Epsom hope after his Racing Post Trophy victory and had won both starts in Ireland at 3, he was only second favourite at Epsom behind his mercurially brilliant stablemate Hawk Wing, the mount of stable jockey Mick Kinane. Both colts were exceptional, and Hawk Wing would have won by 12 lengths had High Chaparral not been in the field! In the event, after rain the emphasis was on stamina at Epsom and High Chaparral always looked in command of this internecine duel as the pair pulled miles clear of subsequent Dubai World Cup winner Moon Ballad.
3. Australia (2014)
Sire: Galileo
Jockey: Joseph O’Brien
Odds: 8/13 favourite
Best RPR 129; Derby RPR 125
A chestnut colt with a narrow white blaze, Australia could hardly have been any better bred for Epsom, for not only was he by the legendary dual Derby-winning sire Galileo, his dam was 7-length Oaks winner Ouija Board. He certainly inherited a deal of his parents’ talent, and was a strong favourite for the Derby after looking an unlucky third behind pure milers Night Of Thunder and Kingman in a red-hot Guineas, where he raced on the ‘wrong side’ and was beaten less than a length.
Clear number one among four O’Brien runners at Epsom, Australia was impressive, responding to pressure to win ridden out from strong stayer Kingston Hill, the subsequent St Leger winner, who took up the running two furlongs out and clearly wasn’t stopping. After a bloodless triumph at the Curragh, Australia's mettle was tested again by The Great Gatsby as he successfully cut back in trip in the Juddmonte International. His career ended in narrow defeat to the same horse in the Irish Champion Stakes, where the winner turned the tables under a fantastic ride from Ryan Moore.
4. Camelot (2012)
Sire: Montjeu
Jockey: Joseph O’Brien
Odds: 8/13 favourite
Best RPR 126; Derby RPR 126
If you could stop looking at Camelot’s career record at halfway, then he looks an absolute world-beater, unbeaten in five – four of them in G1 company, including the 2000 Guineas and the Epsom/Curragh Derby double. The trouble is that he ran five more times, winning just a G3 event on his return as a 4-year-old after major surgery for colic.
Still, you couldn’t argue with his display at Epsom, where he fully justified odds-on favouritism with an authoritative victory, quickening in brilliant fashion from off a solid pace set by stablemate Astrology (who came third) before scoring by five lengths eased down from Main Sequence.
Now the caveats: this was a weakish field, the smallest since 1907 with only nine runners, and Camelot wasn’t as impressive next time in beating only four rivals on heavy ground in the Irish Derby. A brave bid to emulate Nijinsky by completing the Triple Crown in the St Leger deserved to succeed but he was beaten into second by Encke, representing subsequently disgraced Godolphin trainer Mahmood Al Zarooni, after which he flopped in the Arc. He was never the same horse again after his illness and, given the holes in his 3-year-old form, his legacy is mixed.
5. Anthony Van Dyck (2019)
Sire: Galileo
Jockey: Seamie Heffernan
Odds: 13/2
Best RPR 121; Derby RPR 119
The very antithesis of a ‘cottonwool’ Derby victor, ill-fated Anthony Van Dyck ran no fewer than 19 times in a 3-year career in which he danced every dance, visiting the USA, Hong Kong and Australia in the process.
A highly rated 2-year-old in a busy seven-race campaign, this hard-knocking Galileo colt was deserted at Epsom by Ryan Moore, despite having returned with ready victory in the Lingfield Derby Trial. Betting agreed: Stablemate Sir Dragonet and Moore were made 11/4 favourite after an 8-length Chester Vase romp, with Seamie Heffernan-ridden Anthony Van Dyck a 13/2 chance. O’Brien wasn’t done there, as he saddled a formidable seven horses in a 13-runner field, among them G1 performers like Japan, Circus Maximus and Sovereign, who duly made the running as a 50/1 shot with stablemate Norway in close attendance. In the end, four of them were involved in tight finish, separated by less than a length as Anthony Van Dyck got home on the rail to beat Kevin Prendergast-trained interloper Madhmoon by a half-length. After that, the distances were a nose, a short head, and a short head; Ballydoyle horses went 1-3-4-5-6-8-10.
Solid rather than sensational, the winner won only one more race (beating Stradivarius in the Prix Foy as a 4-year-old) but probably should have won the Irish Derby. He suffered a fatal injury shouldering topweight in last year’s Melbourne Cup, having previously finished a head second to the mare Verry Elleegant in the Caulfield Cup.
6. Ruler Of The World (2013)
Sire: Galileo
Jockey: Ryan Moore
Odds: 7/1
Best RPR 125; Derby RPR 121
Ryan Moore’s only Derby winner for O’Brien, though he also won on the Sir Michael Stoute-trained Workforce in 2010. Unseen at two, Ruler Of The World was having only his third start at Epsom, where he was joined by four stable companions, including two well-fancied types in Battle Of Marengo and Mars. A messy race ensued, and a lack of pace hardly helped hot favourite Dawn Approach, the Guineas winner who pulled throughout and finished last, looking as if he wouldn’t have stayed in a taxi.
Having won the Chester Vase on his previous outing, Ruler Of The World picked up well and, despite edging left under camber, galloped on strongly to hold surprise Dante winner Libertarian. The form, though, had a shaky look and he was odds-on fifth in the Irish Derby, and his only subsequent win in eight further starts (admittedly, some tough assignments) came as a 4-year-old in the Prix Foy though he did produce a career-best when beaten only three-quarters of a length by Farrh on favoured soft ground in the Champion Stakes.
7. Wings Of Eagles (2017)
Sire: Pour Moi
Jockey: Padraig Beggy
Odds: 40/1
Best RPR 121; Derby RPR 121
The son of Coolmore’s French-trained Derby winner Pour Moi never really got the chance to prove himself after his shock Epsom success, where he stayed on strongly under rarely seen Ballydoyle backroom boy Padraig Beggy to thwart much better-fancied stablemate Cliffs Of Moher inside the final furlong with Cracksman third.
O’Brien had six fo the 18 runners in the Classic, and only 66/1 chance The Anvil (17th) was less well regarded in the betting. Ballydoyle ensured a strong gallop as Douglas Macarthur and The Anvil established a clear lead before Cliffs Of Moher swooped inside the final furlong – only for Wings Of Eagles (hampered early, raced in rear) to come from the clouds and stun the racing world.
His only other win was a minor Killarney 2-year-old maiden; he sustained a career-ending injury when a close third behind Epsom sixth Capri and Cracksman in Ireland four weeks later and is now a jumps stallion.
8. Serpentine (2020)
Sire: Galileo
Jockey: Emmet McNamara
Odds: 25/1
Best RPR 121; Derby RPR 121
The jury is still out on Serpentine, who still just about has time to prove his spectacular triumph in last year’s Covid-delayed July Derby wasn’t any shade of fluke. What it was, though, was memorable – or memorably bizarre.
Sent off 25/1 under little-known rider Emmet McNamara as part of a 6-strong Ballydoyle brigade, the son of Galileo had broken his maiden only a week earlier at the Curragh. Seemingly ignored by his opponents, he made virtually all and was 12 lengths clear as they exited Tattenham Corner. He wasn’t for catching and stayed on to win unchallenged by five lengths from Khalifa Sat, with 66/1 stablemate Amrhan Na Bhfiann taking third in a race where nothing came from off the pace.
The post mortems continued for weeks – was Serpentine any good or were rival jockeys asleep at the wheel? We still don’t really know. He ran twice more at three, not disgraced when making the frame in G1 company but hardly setting the world alight. His distant seventh on heavy ground in the G1 Tattersalls Gold Cup at the Curragh on May 23 was not a promising start to his 4-year-old campaign.