THERE are very few sports events in the world where people invest an inordinate amount of time and energy trying to predict their outcomes many months in advance. But that’s the Cheltenham Festival for you.

It’s difficult to pick winners at the most competitive racing festival in the world when you actually know which race your horse will run in, the state of the going on the day, the full field in the race and the most recent form of each of the runners. So longterm bets really are the ultimate shot in the dark.

However, occasionally, ante-post miracles do happen. The best recent example of that was Conor Murphy, a stable lad at Nicky Henderson’s Seven Barrows stables at Lambourn. Conor turned a £50 accumulator bet into a cool £1,000,000.

Henderson accumulator

Just before Christmas 2011, Conor placed a £50 five-horse accumulator on five of his boss’s inmates winning their respective races at the 2012 Cheltenham Festival. Sprinter Sacre (6/1 – all odds stated were received when his bet was placed) began his winning sequence with a win in Tuesday’s Arkle Chase, Simonsig (12/1) followed up in the Neptune Hurdle on Wednesday and then came Bobs Worth’s win (6/1) in the RSA Chase and Finian’s Rainbow (8/1), who Murphy used to ride out himself, won the Queen Mother Champion Chase. Riverside Theatre (10/1) then brought up the final leg of this remarkable accumulator when he snatched victory in the dying strides in Thursday’s Ryanair Chase.

It was a life-changing day for Murphy, who on the strength of his winnings set up his own training operation in Kentucky, appropriately named Riverside Bloodstock, as a hat-tip to the horse that had secured his fortune.

Nicky Henderson said that when the bet was placed the odds on all five horses actually running at the Cheltenham Festival was probably around 100/1. Murphy actually ‘won’ £3,153,100, but as Bet365 capped their maximum payout at £1 million, that’s what Conor got paid. It was, and will always be, considered one of the greatest ante-post bets in Cheltenham Festival history.

Annie Power

Murphy’s failure to split his stake had saved bookmakers a couple of million pounds but Annie Power’s infamous fall at the final hurdle in the 2015 Mares’ Hurdle was the most expensive bullet layers have ever dodged.

On the morning of Tuesday, March 10th 2015, a good friend of trainer Willie Mullins sent him a text: “I wish you the worst day in bookmaking history”. He almost got his wish. Annie Power’s dramatic fall at the final hurdle ultimately saving bookmakers a massive payout, estimated to be somewhere in the region of €100 million.

An army of casual punters had decided to place roll-up accumulators on one of the biggest betting days of the entire year on Douvan, Un De Sceaux, Faugheen and Annie Power winning their respective races. All four were trained by Willie Mullins and ridden by Ruby Walsh.

Nightmare

There was a clear and present danger for the bookmakers as they were undoubtedly the best horses in their races. The first three duly obliged and layers were facing their ultimate nightmare when 4/7 shot Annie Power approached the final hurdle with the race at her mercy. But she fell at that final flight to the collective audible gasps from the 62,249 crowd present that day. Frankie Dettori’s 1996 Magnificent Seven at Ascot had cost bookies over €50 million but this would have given them a much bloodier nose. It was the great escape.

‘Fearless Freddie’

For many decades, the betting ring at the Cheltenham Festival simply throbbed. It was the site of some of the biggest bets ever placed. The late bookmaker Freddie Williams, or ‘Fearless Freddie’ as he was affectionately known, was the undisputed king of that particular jungle. Freddie was an old-fashioned layer who bet to his opinion. If you disagreed with him, he would happily accommodate you for as much as you would like to bet.

Freddie was pretty good at his job – he left an estate worth over €8 million. Freddie came from the coalmining hamlet of Cumnock, South Ayrshire in Scotland, was bedridden as a child by polio and began his working life sweeping the floor of a lemonade factory. He rose to manager and, following a management buyout, made the first part of his fortune as a significant player in the fizzy drinks business.

Freddie went on to own a number of betting shops but it was laying on-course bets that Freddie showed his real effervescence. “I get a real buzz from the betting ring. There is a constant challenge. The reward is not always important. The betting shop is just like selling Mars bars. People come in and give you money. Cheers. The only decision you make is whether to open the door in the morning,” he said.

Battles with J.P.

The democratisation of the allocation of on-course betting pitches saw Freddie move into the big league and his battles with intrepid punter, J.P. McManus, would become the stuff of legend. Their duels were unflinching. No quarter was given or taken. And all with a nod and a gentleman’s agreement.

One day at the Cheltenham Festival in 2006, Freddie lost almost £1 million to J.P., who had successfully bet £100,000 on Reveillez at 6/1 to win the Jewson Novices’ Handicap Chase and had then invested £5,000 each-way on Kadoun at 50/1 to win the Pertemps Final, which he duly did.

To add insult to injury, Freddie’s Jaguar was attacked by masked raiders on his way back to his hotel that evening and £70,000 stolen from his boot. It could have been a lot worse. “They obviously weren’t racing fans, otherwise they would have known I had just been cleaned out,” said a philosophical Freddie.

High-roller

J.P. McManus wasn’t the only big punter the bookmakers had a healthy respect for. Poker player Noel Furlong was another legendary high-roller whose punting was not for the faint hearted and very few Cheltenham gambles have captured public imagination quite like the Destriero coup of 1991.

Furlong, one of the biggest operators in the carpet business in both Ireland and Britain, had relieved Ladbrokes of £1,000,000 when his former crock, The Illiad (backed from 33/1 into 7/1), had bolted in at Leopardstown in the 1991 Ladbroke Hurdle. It was a timely coup that provided Furlong with much needed funds to discharge an outstanding VAT bill of £500,000.

The poker ace then decided to reinvest £300,000 of his winnings on his Destriero to win the Supreme Novices’ Hurdle at odds up to 6/1. The money was placed in small sums around various offices to disguise the coup. He also had varying amounts on the double with Destriero and The Illiad to win that year’s Champion Hurdle.

Destriero was unbeaten but was not given a Christmas engagement to protect his price. He duly romped home at Cheltenham by four lengths from future Champion Hurdler Granville Again.

Luckily for the bookmakers, The Iliad fell in the Champion Hurdle to thwart the biggest killing in racing history, but Furlong had once again ensured a handsome return on his investment. He wasn’t finished there. He also had a massive punt on 1999 Grand Annual Chase winner Space Trucker and later that year made global headlines winning the World Poker Championship in Las Vegas and banking $1 million for his card-playing prowess.

Greatest certainity

Not all Cheltenham gambles were quite as well disguised as Furlong’s. Some were in plain sight and actively encouraged by connections.

Back in 1998, champion trainer Martin Pipe said that his Unsinkable Boxer was “the greatest certainty ever to set foot on Cheltenham Racecourse”. It was a remarkable statement from the man who had nursed this strapping gelding through a litany of problems with his legs and his blood vessels.

Boxer unsunk

While at Pond House, Unsinkable Boxer had rapidly risen up the handicap – by 34lb to be precise – and his trainer regarded him as a potential Grade 1 contender, so he was adamant that a three-mile, two-furlong handicap hurdle was a penalty kick for his ‘machine’. He was 100% right. Unsinkable Boxer attracted one of the biggest festival gambles of all time and romped home to the roars of the appreciative crowd who had backed him all the way down to 5/2 favourite and were reported to have taken a seven-figure sum from bookmakers.

Deathly silence

The win was greeted with deathly silence along the rails. Even the normally undemonstrative A.P. McCoy uncharacteristically stood up in his irons and waved his whip to the jubilant hordes a full 50 yards from the winning post. Bookmakers were sick of the sight of McCoy that year as he rode a quick-fire well-fancied treble on the last day of the meeting with Edredon Bleu, Cyfor Malta and Blowing Wind responsible for another day of heartache for the brethren of the satchel.

Aeroplane Xenophon

A few years later, in 2003, Irish trainer Tony Martin, another man feared by the layers for his ability to lay one out for a big handicap, carved his name indelibly into the history of great Cheltenham gambles.

Xenophon had won the valuable Pierse Hurdle at Leopardstown in January and, despite a not inconsiderable 13lb hike in the weights to a mark of 130, he was considered by his jockey Mick Fitzgerald to be an “absolute certainty” for the Coral Cup at Cheltenham.

So much so, that Fitzgerald made a special request to his boss, Nicky Henderson, to be let off riding whatever Seven Barrows might send for the race.

His gaffer duly obliged and Fitzgerald kept the ride on the horse that attracted some hefty bets and was backed down from 20/1 in the ante-post markets, then from 8/1 all the way into 5/2 favourite on the day of the race.

Fitzgerald had considered Xenophon “an aeroplane” and was spot on in his assessment. Xenophon had a ton in hand, winged the final hurdle and sprinted clear up the Cheltenham hill to win by over three lengths.

The bookmakers had once again been absolutely taken to the cleaners by the Co Meath trainer, who went on to have many more great days at the Cheltenham Festival.

There is a tale, possibly apocryphal, that Xenophon, who was owned by the large Drogheda-based Lane Syndicate, was walked in and out of the racecourse many times on the morning of the race, with a different member of the syndicate accompanying him each time. No point in paying the expensive admission fee when you don’t have to! It certainly did Xenophon no harm at all.

Cheltenham legends

Some horses win multiple times at the Festival and go on to become Cheltenham legends. The real skill is to identify that potential long before it reveals itself.

Trainer Jimmy Fitzgerald not only spotted that Forgive’N Forget was something special but he also put his faith in 19-year-old Mark Dwyer, who would go on to become of the greatest jockeys Ireland ever produced.

Forgive’N Forget won the 1985 Gold Cup and a host of other top chases, but when he lined up two years earlier for the Coral Golden Hurdle Final – now the Pertemps Hurdle – one of the most competitive handicaps of the entire year, he was the backed as though defeat was out of the question.

One of the brains behind that gamble was the legendary shrewd Barney Curley, who had sold Forgive’N Forget to Co Roscommon builder Tim Kilroe. Curley and Fitzgerald were certainly aware of just how good he was and from the moment the race weights were announced, a big plunge on Forgive’N Forget began and it never stopped.

By the times the tapes went up, Forgive’N Forget had been backed from fancy double-digit prices into 5/2 favourite. Mark Dwyer made sweet progress throughout the race and produced him to lead going over the last, steering Forgive’N Forget to a three-length success. It is estimated that £1 million was won that day in 1983, equal to £3.5 million in today’s money. It remains one of the biggest ante-post gambles in the history of Cheltenham.

Donovan’s success

Finally, J.P. McManus has gone on to become the most successful owner in Cheltenham Festival history but Mister Donovan’s success in the 1982 Sun Alliance Novices’ Hurdle was a seminal moment in his life.

“I often wonder whether I would have been able to have any of the others if Mister Donovan had been beaten,” said the man of few words who has subsequently gone on to have a record total of 71 Cheltenham Festival winners to date including nine Champion Hurdle victories, three of which were won in successive years by the brilliant Istabraq.

The victory of Mister Donovan was improbable. Four defeats from his four starts over hurdles before Cheltenham, the last of them when third at odds of 25/1 in a Naas maiden hurdle.

Mister Donovan’s future had looked decidedly bleak when he was diagnosed with a heart condition by leading veterinary surgeon Demi O’Byrne. However, trainer Edward O’Grady saw enough potential in the horse to encourage McManus to buy him the month before Cheltenham.

McManus, who had some chastening experiences at Cheltenham in the years previous, had plunged heavily on Mister Donovan from an opening show of 7/1 down to 9/2.

Ironically, Mister Donovan would go on to win under jockey Tommy Ryan, beating Spiders Well, a Josh Gifford-trained gelding ridden by Bob Champion in the colours of the aforementioned Demi O’Byrne.

It’s estimated that J.P. McManus took £250,000 out of the Cheltenham betting ring that day but in typically modest fashion he would later say “I don’t remember quite how much we had on but it was important at the time anyway.”

There’s no doubt that J.P. McManus has enjoyed every gamble he has ever landed at Cheltenham, but this was the one that undoubtedly shaped his future.?