The Derby king: how six of the best at Epsom helped to keep Sir Michael Stoute at the top for more than 40 years

Sir Michael Stoute's quiet exit from the world of racing meant that 2024 marked the end of one of the sport's most extraordinary careers. Below, Julian Muscat explores his six Derby winners, while in this Big Read, available to Members' Club Ultimate subscribers, Muscat looks at Stoute's remarkably eclectic introduction to the sport, from his roots in Barbados and rejection by the BBC to his first steps as a trainer. Not a member? Sign up here and enter code MEMBERS24 upon completion of your purchase to get your first three months for half-price.

Chroniclers of racing in the 1970s were in no doubt that Sir Michael Stoute was destined for great things. Very few trainers saddle a Derby winner in their lifetimes but Stoute bagged his first in 1981, less than a decade after he had opened for business, aged just 26, in 1972.

Derby winners remain the sport's hardest currency and Stoute would plunder five more, culminating with Desert Crown in 2022. In the modern era only Aidan O’Brien has trained more.

Stoute had already turned heads by the time Shergar opened his Derby account in 1981. He hit the ground running in his second season in 1973, when he won eight sprint handicaps with a pair of three-year-olds: Blue Cashmere, who plundered the Ayr Gold Cup, Northumberland Sprint Trophy and Trafalgar House Handicap among his four victories, and Alphadamus, who won the William Hill Gold Trophy and Stewards' Cup.

Among those struck by Stoute's early prowess was fellow trainer Jeremy Tree, who was unable to use his parched gallops at Beckhampton in 1976 and so sent Stoute a pair of talented older horses to make use of the woodchip gallop recently installed up Long Hill in Newmarket. They included Bright Finish, who won the Jockey Club Cup that year under the watchful gaze of Sven Hanson, a Swede who was most impressed by the glistening sheen on his bay flanks. Having just bought four yearlings at Tattersalls earlier that week, he resolved there and then to send them to Stoute. One of them was Fair Salinia, who landed the Oaks, Irish Oaks and Yorkshire Oaks in 1978.

Fair Salinia's exploits in 1978 were complemented by those of Shangamuzo, a second Group 1 winner for the trainer inside three weeks when he won the Gold Cup at Ascot. Watching all this unfold from a distance was the Aga Khan IV, whose forebearers had not had horses trained in Britain for 15 years. That would change when the Aga Khan sent Stoute his first batch of yearlings towards the end of 1978. In the second batch was Shergar, a colt of bewitching brilliance.

More than his exaggerated winning distances in the Derby trials, Shergar exuded a quality that was hard to define in words. His hooves barely seemed to touch the ground when he galloped, and when asked to accelerate he did so almost imperceptibly. The only visual clue that Shergar had reached full throttle was the sight of his opponents melting into the distance.

After his ten-length stroll in Sandown's Classic Trial and a 12-length romp in the Chester Vase, the only surprise about Shergar's Derby triumph was the fact he was sent off at 10-11. He should have been virtually unbackable. His ten-length winning margin is a record that still stands and fully vindicated the opinion of Richard Baerlein, a doyen of the press room who had long advised his Guardian readers to "bet like men".

Shergar's 1981 Derby win proved to be the start of something specialCredit: Gerry Cranham (racingpost.com/photos)

Shergar followed up with victories in the Irish Derby (four lengths) and the King George (four lengths), after which he was roundly and inexplicably beaten in the St Leger. He started at 2-5, odds which reflected his aura of invincibility, but Stoute later berated himself for running the horse.

No matter: Shergar's Derby triumph asserted that his trainer had the golden touch, a quality that separates the great from the good. Shergar's deeds also earned Stoute the first of his ten trainers' titles with apposite timing, since the Maktoum family's involvement in Britain was rapidly gaining momentum.

By the time Stoute claimed his second Derby, with the Aga Khan's Shahrastani in 1986, Stoute had saddled Classic winners for Dubai's ruler Maktoum Al Maktoum (Shareef Dancer and Shadeed) together with Group 1 winners for its crown prince Sheikh Mohammed (Ajdal and Sonic Lady). The stable's list of patrons was beginning to read like a who's who of the turf.

Like Shergar, Shahrastani followed up his Derby triumph by winning the Irish equivalent by eight lengths, but the son of Nijinsky could not escape the shadow of Dancing Brave, who confirmed he was an unlucky loser at Epsom when he defeated Shahrastani in the King George and Arc.

Shahrastani holds off Dancing Brave in the 1986 DerbyCredit: Mark Cranham (racingpost.com/photos)

At that time the Derby's prize-money was such that winning it all but assured Stoute of a second trainers' title. Stoute duly claimed it, although his big-race CV in 1986 was formidable. It embraced the Group 1 victories of Ajdal (Dewhurst Stakes), Colorspin (Irish Oaks), Green Desert (July Cup, Haydock Sprint Cup), Ivor's Image (Oaks d'Italia, E.P. Taylor Stakes), Shardari (International Stakes), Sonic Lady (Irish 1,000 Guineas, Sussex Stakes, Prix du Moulin) and Untold (Yorkshire Oaks).

All went swimmingly for the next two years – until Aliysa's victory in the 1989 Oaks precipitated a sequence of events that would culminate with the Aga Khan withdrawing all his horses from Britain.

Aliysa showed traces of a metabolite of the prohibited substance camphor in her post-race test, and was duly disqualified. The Aga Khan hired a team of experts to investigate and their conclusions included an assertion that the ruling Jockey Club's anti-doping procedures were amateurish at best.

However, when the club stood by its decision to disqualify Aliysa, Stoute lost 60 of the Aga Khan's horses. It was the sort of reverse that could have undermined him. Instead, he made light of it until the Aga Khan returned in 1995, after which the reforged alliance enjoyed a seminal year in 2000. The new millennium's dawn saw Daliapour land the Coronation Cup and Kalanisi claim the Queen Anne Stakes, Champion Stakes and Breeders' Cup Turf.

Nevertheless, 17 years would elapse between Shahrastani's Derby triumph and Stoute's third winner of the blue riband – Kris Kin in 2003. Stoute hardly marked time in the interim. He won four more trainers' titles (1989, 1994, 1997 and 2000), when a host of champions passed through Beech Hurst and Freemason Lodge – the latter stable acquired from Sir Cecil Boyd-Rochfort in the mid-1970s.

Two standouts from that period were contemporaries in age who made their mark internationally. Pilsudski was a late bloomer who closed his four-year-old season by winning the Breeders’ Cup Turf from his stablemate Singspiel in 1996. Pilsudski made further lucrative gains the following year, when he reeled off victories in the Eclipse, Irish Champion Stakes, Champion Stakes and Japan Cup.

Meanwhile, Singspiel was taking huge strides of his own. Most commentators dismissed Singspiel as something of a soft touch when the colt was beaten four times in photo-finishes as a three-year-old in 1995, but Stoute never lost faith.

After chasing home Pilsudski in the Turf, Singspiel ventured to Tokyo to win the Japan Cup. Yet he was even better as a five-year-old in 1997, when he ran amok. He backed up his victory in the Dubai World Cup, on his first start on dirt, with equally comprehensive triumphs in the Coronation Cup and International Stakes.

Singspiel was the last top-class horse Stoute trained for Sheikh Mohammed, whose entire focus switched to his Godolphin stable. It had been a bountiful alliance: among the Group 1 winners Stoute trained for the sheikh were Ajdal, Melodist, Musical Bliss, Opera House, Shaadi, Sonic Lady and Unite, as well as Singspiel. The two men also aligned for an unlikely Champion Hurdle victory with Kribensis in 1990.

Ajdal was particularly charismatic. Having won the Dewhurst Stakes as a two-year-old, he was beaten in the 2,000 Guineas, Irish 2,000 Guineas and the Derby. His limitations were seemingly exposed but Stoute brought Ajdal back to six furlongs for the July Cup – which the colt won en route to claiming champion sprinter honours with further triumphs in the Nunthorpe Stakes and Haydock Sprint Cup. Stoute would later describe Ajdal's participation in the Derby as "one of the biggest cock-ups".

The fact Ajdal was a rare Group 1-winning juvenile for Stoute underlined the trainer's patient approach with horses. He ran them sparingly, only when they were on their mettle, and loved nothing more than watching them flourish at four and five.

Sheikh Mohammed's departure from the stable came at a time when his brother Sheikh Maktoum was also scaling back his racing interests. In addition to the aforementioned Shadeed and Shareef Dancer, Stoute trained further Group 1 winners for Sheikh Maktoum in Ezzoud, Green Desert, Soviet Line and Zilzal.

Yet Stoute mitigated the sheikhs' absence by attracting well-established patrons in the shape of Sir Michael Sobell/Sir Arnold Weinstock's Ballymacoll Stud, Cheveley Park Stud, Khalid Abdullah, and of course Queen Elizabeth II. He also took on horses owned by Sheikh Hamdan Al Maktoum, and it was that connection which propelled him into the winner's enclosure on Derby day for the third time in 2003.

Kris Kin ends Sir Michael Stoute's 17-year wait for a third Derby winnerCredit: George Selwyn

Kris Kin was owned by an acquaintance of the Maktoum family in Saeed Suhail. The colt had been entered in the Derby as a yearling but was scratched in October of his two-year-old season, when he'd finished unplaced on his sole start to that point. So when he won the Dee Stakes by two lengths as the 20-1 outsider of four, Suhail had to stump up the Derby supplement of £90,000 to re-engage him.

Stoute was unsure what to make of Kris Kin, who he described in the Derby preamble as one of the laziest horses to pass through his hands. But with Kieren Fallon aboard, Kris Kin justified strong support when he collared The Great Gatsby inside the final furlong at Epsom.

Having sprung from anonymity, Kris Kin returned to it after the Derby. He ran on strongly from the rear to finish third in the King George, after which he was never sighted in the Arc. Yet Stoute had cajoled enough from this quirky customer – he'd shed his jockey soon after passing the post in the Dee Stakes – to win an admittedly poor running of the Derby.

Twelve months later and Stoute was back in the hallowed winner's enclosure at Epsom, this time with the Ballymacoll Stud homebred North Light. For the colt's prep race Stoute chose the Dante Stakes, which North Light approached having won the second of his two starts as a juvenile.

A cosy defeat of Rule Of Law at York set up North Light perfectly for Epsom, where he beat the same horse after Fallon sent him to the front early in the straight. North Light had now won three of his four starts but hopes that he might prove a superior Derby winner were dashed when he succumbed to Grey Swallow in the Irish equivalent – albeit he returned home with a leg injury.

Stoute keenly anticipated North Light's four-year-old campaign but the colt sustained another injury on his seasonal comeback and never raced again. More's the pity, since Stoute had excelled with Ballymacoll homebreds who were renowned for improving with age.

Two in a row: North Light and Kieren Fallon win the 2004 Derby at EpsomCredit: Edward Whitaker

In addition to Pilsudski, others to carry Ballymacoll's pale blue silks included Saddlers' Hall (Coronation Cup), Golan (2,000 Guineas, King George), Yorkshire Oaks winner Hellenic and her daughter Islington, a four-time Group 1 winner including a Yorkshire Oaks brace and the 2003 Breeders' Cup Filly & Mare Turf. The alliance would have one further top-class colour-bearer in Conduit, who completed Stoute’s Classic 'full house' in Britain by winning the 2008 St Leger.

An exceptionally tough colt, Conduit also won back-to-back runnings of the Breeders' Cup Turf, but a more significant landmark saw him lead home a stable 1-2-3 in the 2009 King George when he outran Tartan Bearer and Ask, in the process banking a tenth trainers' title for Stoute.

That trifecta paid handsome tribute to Stoute's prowess, particularly with middle-distance horses. It was a point Stoute reiterated the following season, when Workforce provided him with his fifth Derby winner.

In powering away from At First Sight by seven lengths in a new course record, Workforce evoked memories of Shergar 29 years earlier by the ease of his victory. The world was seemingly at his feet, yet the colt failed to settle in the King George and trailed home well behind his stablemate Harbinger.

Workforce's Derby effort on fast ground appeared to have left its mark. He showed a propensity to hang at Ascot, as he had when beaten in the Dante Stakes, yet Stoute revitalised Khalid Abdullah's homebred to such purpose that Workforce filled a glaring void in his trainer's illustrious CV by winning the Arc in October. He was an outstanding talent on his day.

Workforce romps home at Epsom in 2010 - and would go on to fill a glaring void in his trainer's CV by adding the ArcCredit: Edward Whitaker

It would be three years before Stoute won his next Group 1 race, but the wait was well worthwhile. Excitement was rife in the royal box when Queen Elizabeth II's Estimate came out best in a gruelling finish to the 2013 Gold Cup at Royal Ascot. Stoute was visibly animated afterwards, especially when the queen confided in a euphoric winner's enclosure that the Gold Cup was the race she most wanted to win. No reigning British monarch had previously won the meeting's signature race.

The post-Estimate era saw Stoute's stable retreat from the high standards it maintained over the previous four decades. Most of the owner-breeders who propelled him to the treetops had passed away – with one notable exception.

The Thompson family aligned with Stoute in the late 1980s and their Cheveley Park Stud was a constant thereafter. However, where the likes of Gay Gallanta (Cheveley Park Stakes), Exclusive (Coronation Stakes), Regal Rose (Cheveley Park Stakes), Medicean (Eclipse Stakes), Russian Rhythm (1,000 Guineas, Coronation Stakes, Nassau Stakes, Lockinge Stakes) and Peeress (Sun Chariot Stakes, Lockinge Stakes) were once part of a broader herd at Freemason Lodge, the stud's horses would become Stoute's mainstay.

Stoute posted further Group 1 triumphs for Cheveley Park Stud with Integral (Falmouth Stakes, Sun Chariot Stakes), Queen's Trust (Breeders' Cup Filly & Mare Turf) and Veracious (Falmouth Stakes), but evidence that he was in his career twilight came in 2022, when he vacated Beech Hurst Stables to consolidate his string at Freemason Lodge.

True to form, however, Stoute rebuked those seeking to write him off with a final act of defiance. Twelve years after Workforce gave him his fifth Derby victory, Stoute, then 76, conjured a sixth with Desert Crown.

Desert Crown was Stoute's last great championCredit: Edward Whitaker

Desert Crown was imperious at Epsom, where he travelled with conspicuous ease before bounding clear down the home straight. He looked like an exceptional talent, yet fate dealt him a cruel hand.

Desert Crown missed the rest of the season through injury but returned in 2023 to chase home Hukum on his seasonal debut. It was a promising comeback that should have primed him for the bigger summer tests.

However, a series of niggling setbacks beset Desert Crown until he fractured a fetlock in August and never recovered. Unlike his illustrious trainer, he wasn't able to stand the test of time.

Read more:

Amo Racing expected to take over at Freemason Lodge next year with Raphael Freire set for Newmarket switch 

James Horton excited to move into Sir Michael Stoute's former stables in Newmarket 

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