Cheltenham's greatest gambles, including the £900,000 punt from 66-1 to 16-1

This article was first published in 2020 and has been taken from the Racing Post archives to further whet your appetite ahead of this year's Cheltenham Festival, which is now less than three weeks away . . .

Cheltenham Festival: big-race entries

Son Of Flicka

Coral Cup, 2012

It's the sign of a satisfying plot when a tale appears under the result in the Racing Post that begins, "the trainer said regarding the apparent improvement in form . . . "

If you were on at fancy prices, it's the kind of thing you might want to cut out, frame and hang on the wall, just to raise a chuckle during a bad run of form. If you weren't on, you might feel your hackles begin to rise – but then, that's racing.

Donald McCain was asked to recount such a tale after Son Of Flicka had been backed down from stratospheric odds to land the Coral Cup by a thumping three and a half lengths in 2012.

His mind may have been elsewhere at the time, but he did manage to inform the stewards that "the gelding appreciated the better ground and comes to himself in the spring", all of which seemed to satisfy them and was of no consequence at all to winning punters, who were watching the umpteenth replay of the rejuvenated eight-year-old hitting his peak when it most mattered.

It mattered very much to his owner Phil Williams, the former Crewe Alexandra, Wigan Athletic and Chester City midfielder who enjoyed a lumpy ante-post bet at 66-1 that supplemented the net worth of the Dubai-based businessman by a cool £900,000.

From that figure we have to subtract the tidy sum he lost when the same horse had been inched out by Gigginstown's Sir Des Champs in the Martin Pipe Conditional Jockeys’ Hurdle a year earlier, but we can safely assume that he was up on the deal.

For McCain, the result was about much more than money, with the win coming from a horse who had joined his Cheshire yard at the age of three and been a grand servant ever since, wearing his heart on his sleeves at all times, according to his trainer.

Donald McCain: trained Son Of FlickaCredit: Edward Whitaker

His narrow festival defeat in 2011 came after some admirably consistent runs that had seen his mark rise to 140, but after "a terrible fall" at Aintree off his new perch of 148 he lost his confidence and form completely and was beaten an aggregate distance of 175 lengths on his three outings that winter.

Freshened up by a 60-day break and a little spring sunshine on his back, however, he went to Cheltenham rejuvenated, was soon among the leaders in the 28-runner cavalry charge, clinging grimly to the rail all the way, responded gamely on his favoured good going when asked by Jason Maguire to move into the front rank, then launched a challenge up the middle of the track that carried him clear of Get Me Out Of Here.

"When he's on song he takes some passing," added McCain – a sentiment with which his owner would no doubt concur gratefully.

Unlike many successful landers of monster gambles, Williams had no interest in signing the box marked 'no publicity'.

"I'll die a happy man now," he beamed afterwards. "Last year I was beaten by Michael O'Leary and told him it was the only thing he had ever arranged to arrive at the right place at the right time! It's great – today he was the first person to congratulate me. British jump racing – it's what sport is all about."
Peter Thomas

Forgive ‘N Forget

Coral Golden Hurdle Final, 1983

If we’d known then what we know now, we’d all be millionaires. As it is, we didn’t and mostly we aren’t, but when the 1985 Gold Cup winner lined up two years earlier in what is routinely one of the most fiercely contested handicaps of the big week, off a weight of 11st 6lb having been bought from the legendarily shrewd Barney Curley, what we were looking at was a licence to print money.

Jimmy Fitzgerald knew. So did the horse’s owner, the Cheshire-based Irish construction tycoon Tim Kilroe, but then he was a millionaire anyway. A lot of other people developed an inkling as the race approached, the raceday crowd put its full weight behind the project, and the sheer volume of money from all sources ensured that the six-year-old son of Ascot Gold Cup hero Precipice Wood and five-furlong winner Tackienne was sent off at what may have looked to dissenters like a ridiculously short price. By the time he jumped the last in front and full of running, 5-2 looked like a steal.

Fitzgerald was keenly aware of the talent he had at his disposal – perhaps Curley had even had a quiet word in his ear – and the gamble began from the moment the weights were revealed. Irish bumper winner Forgive ‘N Forget, having already ‘won’ four of his first six hurdle races – being disqualified for interference on the second of them, at Worcester in October – was perched near the top of the handicap, but his successes in handicap company at Catterick and Ayr in January 1983 merely hinted at his true ability.

Subsequent Gold Cup winner Forgive 'N Forget landed a punt in 1983Credit: Gerry Cranham

His tempestuous trainer, from Horse and Jockey in County Tipperary, was renowned as a man who could "lay one out" and the support for the chestnut suggested he had left a little in the locker for a later day, and although his young rider Mark Dwyer lacked the experience of some of his older rivals, confidence never waned, despite the regulation large field and the frantic nature of the event.

Again, if we’d known that 19-year-old Dwyer was to turn out to be one of the brightest talents to cross the Irish Sea in many a year, we’d have all been on. The gifted Irishman kept his mount anchored towards the rear, made sweet progress into third place with three flights to jump, unleashed him to lead at the last and steered him up the hill to a three-length success over Brunton Park.

The talk was of a £1 million coup, in the days when £1 million was a lot of money. If only it were always that easy.

Forgive ‘N Forget raced once more that season, when pulled up at Aintree, but his best days were still in front of him. When switched to fences the following season, he posted an impressive success in the prestigious Timeform Chase at Haydock and ran with great credit in the Sun Alliance Chase, but it was the following season that he truly shone.

Fitzgerald confirmed what we had suspected since March 1983, that this was the best horse he had ever trained and that he would be disappointed if he never won a Gold Cup. The trainer was not to be disappointed, sending Forgive ‘N Forget to win the Rowland Meyrick Chase and the Timeform Chase again, before beating Monica Dickinson’s Righthand Man in the main event at Cheltenham.
Peter Thomas

Unsinkable Boxer

Gold Card Hurdle Final, 1998

When Martin Pipe describes a horse as "the biggest certainty to set foot on Cheltenham racecourse", it's probably time to sit up, take notice and hotfoot it over to the ring to avail oneself of any fancy prices still remaining.

He was never the kind of chap to make such a bold statement to the assembled press and public – at least not before the race – but if the weight of money for Unsinkable Boxer was anything to go by on this punting day of days, it seems that the world and his wife was eavesdropping when Pipe dropped this bombshell on his rider Tony McCoy.

"A machine" was the other choice description offered up by the trainer in the weighing room beforehand, along with the instruction to ride him as though the race were simply another of the moderate novice hurdles the horse had been mopping up at Plumpton, Fontwell and Doncaster, then "pass them when you like".

It was remarkable stuff but Pipe wasn't entertaining an angel unawares. From the moment the horse arrived at Pond House from Ireland – via a troubled spell under the care of new owner Paul Green's stepson Nick Walker – the trainer had an inkling he had something special on his hands, if only he could overcome a litany of problems with his legs and his blood vessels.

This was Pipe, though, and he nursed the fine, strong beast through his problems and rapidly up through the handicap – by a satisfying 34lb – to the point where many regarded him as a Grade 1 contender in the making. In the lead-up to the festival there was talk of a tilt at the Stayers' Hurdle, but it certainly didn't come from the trainer, who was keen to have a bird in the hand and was adamant that the 3m2f handicap represented a penalty kick for the nine-year-old.

Martin Pipe: sent out Unsinkable Boxer to strike in 1998Credit: Edward Whitaker

With McCoy left in no doubt that he should ride the race with the utmost confidence – his only concern being that the sole way the horse could get beaten was if he "mucked it up" – he was happy to sit at the rear of the field, with his biggest problem through the race being, rather ironically, the vast superiority of the horse, which manifested itself in a certain keenness and a quite astonishing response when he gave him a squeeze approaching the middle hurdle on the far side.

Unsinkable Boxer, McCoy said later, passed five horses in mid-air and was travelling so powerfully the champion was forced to give up the unequal struggle before the second-last and let him loose, which was about the moment when the army of punters who had supported him down to 5-2 favouritism let their feelings be known. On-course firms reported that every bet they took was for the favourite, not a single farthing for any other horse, which went some way to explaining the volume of noise.

Backers were encouraged in their vocal histrionics by the winning jockey who, in an uncharacteristic outburst, waved his whip vigorously in the direction of the grandstands with fully 50 yards left to run. There was pandemonium among the crowd as a mighty gamble was landed. A competitive festival handicap had, according to TV commentator Graham Goode, been "turned into a procession" and the queues at the payout windows were long and jubilant.

Green, meanwhile, was reported to have grumbled in the trainer's direction that his horse had been directed at the wrong race and would have won the Stayers' Hurdle had he been allowed to run in it. There was no suggestion that either Pipe, McCoy or a legion of backers shared his reservations as they celebrated what was widely judged to be one of the biggest festival gambles of all time – a very public plot that ended in deathly silence on the rails. Job done in a seven-figure fashion.
Peter Thomas

Destriero

Supreme Novices' Hurdle, 1991

The cast list involved with Destriero is like something from a work of pulp fiction. A poker-playing carpet baron with a hefty tax bill, his greyhound-loving wife with magic healing hands, a down-on-his-luck horseman back in the big time and a little-known jockey with an agonising speech impediment.

Noel Furlong, who made it to the final table at the World Poker Championship in Las Vegas in 1989, netted an estimated £1.5 million when Destriero, owned by his wife Betty, trained by Andy Geraghty and ridden by Pat McWilliams, beat a strong field in the opening race of the 1991 festival.

Destriero's triumph was the sequel to a spectacular gamble landed by Furlong at Leopardstown earlier in the year, and also the prelude to an afternoon of high drama.

The story began at Leopardstown in January 1990 when Destriero, a son of the 1978 King George winner Ile De Bourbon, was an even-money debut bumper winner for Curragh trainer Mick O'Toole, carrying the colours of his daughter Mags.

The four-year-old did not appear again until making his hurdling debut at Leopardstown's Christmas meeting 11 months later, bolting up by 12 lengths. He was now trained by Geraghty, who had slipped into relative obscurity since sending out Doubleuagain to win the Mildmay of Flete at the 1982 Cheltenham Festival.

Destriero: scored in the 1991 SupremeCredit: Mark Cranham

Geraghty was effectively a stand-in for Betty Furlong, whose application to train her husband's string on the Curragh had been rejected by the Turf Club.

Two days later The Illiad, an injury-prone nine-year-old formerly trained by Homer Scott, defied a 364-day absence to land a five-length handicap hurdle victory under 12st on his first run in the Furlong colours. The seeds of a stunning plan had been sown.

The next chapter unfolded in January 1991 when McWilliams rode The Illiad to win the Ladbroke at Leopardstown, landing a £10,000 each-way bet struck by Furlong at 33-1 with the sponsors, as well as scores of smaller wagers at morning prices from 10-1 down to his starting price of 7-1.

Afterwards, the normally reticent Furlong was effusive in his praise of his wife for diagnosing and resolving the back ailment which had previously hindered The Illiad's effectiveness, and had enabled the couple to acquire him for a bargain £2,200 out of Scott's yard.

As Betty Furlong set about preparing Destriero for the Supreme and The Illiad for an ambitious Champion Hurdle tilt, her husband tidied up some unfinished business, arriving at a £500,000 settlement with Britain's Inland Revenue, arising from proceedings initiated for non-payment of VAT a few years earlier.

Noel Furlong: won an estimated £1.5m on Destriero

After seven consecutive Irish victories between 1977 and 1983, the Supreme Novices' had become a graveyard for the visitors. This time two other strong Irish challengers, Jim Bolger's Nordic Surprise and Dermot Weld's General Idea, joined Destriero in a 21-strong field headed by Martin Pipe's ex-Irish bumper winner Granville Again.

Furlong had £300,000 on Destriero ante-post at rates down to the 6-1 starting price. The story of the race is simply told. Destriero was settled well in a prominent position by McWilliams, travelled smoothly through the race and took command from the second-last.

He hit the last hurdle without losing momentum and stayed on powerfully up the hill to beat the subsequent Champion Hurdle winner Granville Again by four lengths.

It was a stunning victory which left bookmakers staring into the abyss as word circulated of massive potential liabilities in respect of ante-post doubles involving Destriero and The Illiad, whose Champion Hurdle price contracted from 12-1 to 11-2 second favourite behind Granville Again's brother Morley Street.

Privately, though, Furlong knew the gamble was doomed. His wife had told him in the morning that all was not well with The Illiad, who trailed in last behind Morley Street to the massive relief of the bookmakers.

Still, Furlong could console himself with the cool £1.5m he had already pocketed.
Alan Sweetman

Mister Donovan

Sun Alliance Novices' Hurdle, 1982

Viewed from a certain perspective, the 1982 Sun Alliance Novices' Hurdle, won by an Irish-trained maiden with a heart murmur, was arguably one of the most influential jump races of the last 50 years.

The significance goes beyond the bare fact that Mister Donovan earned himself a permanent footnote in racing history by becoming the first festival winner in the green and gold colours of JP McManus, the most successful owner in Cheltenham history.

Speaking in 2014, McManus, a man of few and selected words and certainly not given to exaggeration, reflected on his breakthrough winner: "I often wonder whether I would have been able to have any of the others if Mister Donovan had been beaten."

Think about that for a moment and you have to embrace the possibility of a parallel universe in which the mighty Istabraq and a host of other stars might have had an altogether different fate.

McManus fell in love with Cheltenham on his first visit as a bookmaker and punter in the week after his 22nd birthday in March 1973. The following year the Limerick man and his Tipperary associate Jimmy Hayes joined in a large-scale public gamble on the Edward O'Grady-trained and Mouse Morris-ridden Mr Midland in the National Hunt Chase.

McManus joined forces with O'Grady by buying hugely promising chaser Jack Of Trumps, who gave him the first of several chastening festival experiences, coming to grief at the 17th fence when odds-on favourite for the 1978 National Hunt Chase.

The following year O'Grady and McManus believed Deep Gale was another "bar-a-fall" certainty for the four-miler, but he fell six out when cruising. Boots Madden claimed that if only he had been able to hang on to the horse he could have remounted and won. For McManus the pain was accentuated by the fact he had added £40,000 to his stake after backing the Sun Alliance Chase winner Master Smudge at 20-1.

As O'Grady continued to establish his reputation as one of the leading festival trainers, thanks to horses such as Flame Gun, Mountrivers, Drumlargan and Staplestown, his big-punting patron arrived at the 1982 fixture still awaiting a first success.

This time his hopes centred on Mister Donovan, a horse whose future had seemed decidedly bleak when diagnosed with a heart condition by leading veterinary surgeon Demi O'Byrne.

Unable to sell the horse, O'Grady persevered and saw enough potential in his bumper and maiden hurdles run to encourage McManus to buy him in the month before Cheltenham.

Although he was still a maiden, O'Grady felt he had the right profile for the Sun Alliance Hurdle, a race he had won in controversial circumstances with Drumlargan in 1980, leading to a lengthy whip ban for stable jockey Tommy Ryan.

McManus, who had a bad losing day as a punter on the first afternoon of the meeting, plunged heavily on Mister Donovan from an opening show of 7-1 down to 9-2.

The race unfolded in ironic circumstances as Mister Donovan was delivered by Ryan at the last to beat Spiders Well, a Josh Gifford-trained gelding ridden by Bob Champion in the colours of Demi O'Byrne.

O'Grady recalls how McManus commissioned a portrait of the two horses jumping the last and later enjoyed seating O'Byrne around the dinner table at Martinstown with the painting strategically placed in his line of vision.

Contemporary estimates suggest that McManus took £250,000 out of the Cheltenham ring on that fateful afternoon. The man himself has said: "I don't remember quite how much we had on but it was important at the time anyway."

The full measure of that importance is evident from the owner's hint that jump racing history could have been very different if Mister Donovan had joined the list of reverses associated with his early experiences of Cheltenham in the 1970s.
Alan Sweetman

Xenophon

Coral Cup, 2003

Down the years there have been a few trainers the very mention of whose name induces palpitations in the massed ranks of festival layers, and Tony Martin was undoubtedly one.

His ability to see a possible handicap blot was beyond question and his capacity to engineer a big gamble accordingly soon developed into the stuff of legend.

Having said that, he can hardly be accused of having hidden Xenophon's light entirely under a bush in the build-up to this massive Cheltenham gamble.

The seven-year-old had been produced to win the valuable Pierse Hurdle at Leopardstown in January after all, and the 13lb rise he earned for that comfortable success was hardly insubstantial.

It was, however, nowhere near enough to halt the progress of an animal clearly improving far too fast for the handicapper, and the mark of 130 he received was soon made to look laughably inadequate.

Martin, himself a former top-class amateur rider, had tempted Mick Fitzgerald to come over for the ride in the Pierse, and so impressed was the ace jockey in victory – he said Xenophon had felt like "an aeroplane" going to post – that he begged his boss Nicky Henderson to be let off riding anything Seven Barrows might be sending to the race in order to ride what he told Martin was "a certainty".

Luckily for him, Henderson co-operated and Fitzgerald kept the ride on what turned out to be a 5-2 favourite who had been backed at all rates down from 20-1 to substantial ante-post money, then from 8-1 on the day of the race, putting the pressure on the nervous trainer but not so much on the experienced jockey.

The only trouble was that the opposition looked as strong as ever, with Martin Pipe alone fielding nine of the 27-strong field, including Korelo, a hugely progressive five-year-old chasing a substantial cash bonus for owner David Johnson after a bloodless six-length victory in the Imperial Cup at Sandown.

Pipe wasn't known for passing up such riches lightly, but the Irish had their tails up and wouldn't hear of defeat.

Mick Fitzgerald: on board for Xenophon's 2003 Coral Cup successCredit: Alan Crowhurst (Getty Images)

The plan was to sit out the early part of the race and creep into contention, which the super-cool Fitzgerald found straightforward on a horse who had a ton in hand.

Cruising in second gear, the rider was briefly concerned about arriving too soon on the scene, but he encouraged the son of St Leger winner Toulon to miss the second-last – "if he'd winged it, he would have been in front" – met the last on a perfect stride and sprinted clear up the hill to beat Pipe's Samon by a cosy three and a half lengths, with Spectrometer finishing strongly in third.

"That was a hell of a feeling," purred Fitzgerald, although the layers no doubt had a rather different view having been well and truly taken to the cleaners by the trainer from County Meath, whose reputation as a lander of monumental gambles was well and truly cemented into festival history.

Martin continued to thrive at Cheltenham, winning with Dun Doire (2006), Savello (2014) and Rivage D'Or (2015) as well as enjoying his most successful festival when landing the JLT with Benefficient and the County Hurdle with Ted Veale, both in 2013.
Peter Thomas

Reveillez

Jewson Novices' Handicap Chase, 2006

We've already covered the first of JP McManus's great Cheltenham Festival gambles in this series – that afternoon in 1982 when, down on his luck after a dreadful first day, the big-hitting Irishman was rumoured to have picked up £250,000 for his Mister Donovan winning the Sun Alliance Novices’ Hurdle under Tommy Ryan at 9-2.

That was the first of many famous McManus festival gambles, several of them still memorable to this day.

For sheer last-flight drama, who could forget the moment when Like-A-Butterfly and Charlie Swan looked cooked in the 2002 Supreme but took advantage of the fall of Adamant Approach to land some lumpy bets for her fortunate owner.

A grateful nation, who had piled on to the mare as though defeat were an impossibility, breathed a sigh of relief at her 7-4 triumph.

Then there's the 2013 Grand Annual won by Alderwood, hero of the previous year's County Hurdle, who ended up a 3-1 shot due to weight of money and delivered with barely a moment's fuss – Kid Cassidy getting the McManus forecast up for good measure.

But pride of place surely must go to Reveillez, a former useful Flat horse springing from the unusual source of James Fanshawe's Newmarket yard to annex the 2006 Jewson Novices' Handicap Chase.

It wasn't a dramatic victory but it was notable as a monster slugfest between McManus and 'arch-enemy' Freddie Williams, two of the biggest characters and most fearless players in the Cheltenham ring.

McManus took his biggest swing, asking for a bet of £100,000 at 6-1, and Williams, far from running for cover, accommodated him without turning a hair. When the favourite in the green and gold obliged at 9-2 – jubilant punters were reportedly seen stuffing used, non-sequential notes into black bin bags, with wallets proving wholly inadequate – the bold layer may have thought the day couldn't get any worse, but when McManus stepped in again things did.

JP McManus: heavily backed Reveillez in the 2006 JewsonCredit: Edward Whitaker

The knockout blow was a £5,000 each-way tilt at 50-1 shot Kadoun in the Pertemps Final, and while Williams may briefly have clung to hope of salvation when the live outsider and his partner Tom Ryan blundered at the final flight, this was McManus's day and nothing could stop the juggernaut.

"I couldn't let him run loose at 6-1," was JP's assessment of the Reveillez punt, but if AP McCoy felt the weight of cash on his shoulders he never showed it. He was still on the trail of his first festival winner for his new boss but the pressure didn't have a chance to build as he steered the seven-year-old grey round without major incident.

There was a public inkling that the previous year's Royal and SunAlliance Hurdle fourth might be well treated off a mark 10lb shy of his hurdles rating, but to this point his only chase win had been in a Folkestone novice event. Fears, however, were soon allayed.

Tracking the leaders, he was just moving into a challenging position when he hit three out, but it was a hindrance more than a catastrophe and he soon hit the front, coasting down the hill, responding well to such urging as was required and staying on well up the final gradient, despite idling, to hold the challenge of Nicky Henderson's Copsale Lad by a length and a quarter, with Tumbling Dice another nine lengths back in third.

The noise of the crowd was surpassed only by the rustling of bank notes as the layers readied themselves for payout time.
Peter Thomas

Read more on the Cheltenham Festival:

Race of the week? Assessing the top Supreme contenders

The key British formlines you need to follow at this year's Cheltenham Festival

The key Irish formlines you need to follow at this year's Cheltenham Festival

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