Cheltenham's all-time favourites: Horse racing's big festival celebrates its centenary

Robin Oakley profiles the people who've made it an odds-on winner

Nicky Henderson has handled more Cheltenham Festival winners than anyone still training. This year, he could top the all-time list and he has no doubt why the Festival matters: "Every time you buy a horse you start with a dream. The owner who doesn't think of his horse as a potential Cheltenham Festival horse is rare indeed."

This is the hundredth year of Cheltenham. It was in 1911 that the course, set in the Gloucestershire countryside beneath Cleeve Hill, became the permanent home of the National Hunt Chase, a four-mile steeplechase for amateurs at that stage seen by the National Hunt Committee as the most important jumping race in the calendar and which had previously roamed around a selection of courses. Now Cheltenham's four-day Festival, which starts on Tuesday, is an event which tests the livers and wallets of its passionate spectators as much as it does the courage, stamina and skill of the horses and riders. It is acknowledged as the jumping Olympics, and the Gold Cup its 100m final. The Festival scarcely has to advertise: jockeys and trainers unsaddling in winners' enclosures elsewhere throughout the season frame most of their comments in terms of the horses' Festival potential.

To get there Cheltenham – where racing first started in the early 19th century, has had to survive the excoriations of local hellfire preacher Dean Francis Close, who perceived the sport as a magnet for every kind of sin from gambling to fornication and whose followers once burned down an early grandstand. Then , after the First World War, it provided backbone as a new generation of tough young farmers sons took over from the devil-may- care subalterns of cavalry regiments who had dominated the previously largely amateur sport.

Cheltenham's early professionalism and race programming helped to build a public following for the winter sport which had long been a poor relation of flat racing. After the Second World War it became a focus for the friendly but intense Anglo-Irish rivalry which is a key theme of modern Festivals – along with a frantic betting market – £150m a day is gambled at the Festival, which provides a tenth of the Tote's annual turnover.

The real stars of course are the horses – equine heroes like Arkle and Mill House, Kauto Star and Denman, Desert Orchid and Dawn Run, Istabraq and Sea Pigeon, Best Mate and Moscow Flyer. But many on two legs have played key roles along the way, here are four of the most prominent.


The founder

It was Frederick Cathcart's dream to make Cheltenham the home of National Hunt racing. Cathcart, who came from a business providing secretariats for racecourses, was the first chairman of the Cheltenham Steeplechase Company in 1907. He cleaned up the quality of stewarding (there had previously been cases of officials not disciplining riders and trainers who blatantly manipulated form and then using that information to back the horses the next time they ran). He oversaw the building of a new stand and laid out a new course. But with the Grand National in those days carrying a prize out of scale with any other jump race his crucial contribution was the introduction of a genuine championship race, the Gold Cup, in 1924, a year after he turned Cheltenham into a three-day event.

The Grand National had always been and still is a handicap with horses allotted weights designed to give every one a chance. The Gold Cup was to be a weight-for-age steeplechase, with horses of normal racing age carrying the same weight and running over normal fences, not the then huge Aintree obstacles. In 1927 under Cathcart's regime the Champion Hurdle was introduced as a similar contest for horses racing over the smaller obstacles. True championship racing had arrived.


The eccentric owner

In the 1920s new-style horses such as Easter Hero, built for speed as much as endurance, arrived on the jumping scene but the sport needed character and personality. Enter Dorothy Paget. She had been a fine horsewoman in her youth, hunting, showing and riding in point to points, but she grew so obese that she looked twice her age. She was the owner of a vast chain-store fortune inherited from her maternal grandfather, William Whitney, and it was racing's good fortune that she diverted much of it into buying horses, having been fired with enthusiasm for the sport by her cousin Jock Whitney's success with Easter Hero.

Paget suffered from a chronic shyness and an aversion to men. When she used to visit racecourses, clad in a shapeless tweed coat and a beret, wearing no make up and with unstyled cropped hair, she would be accompanied by a posse of protective female secretaries. Contemporaries told of her locking herself in a lavatory until most racegoers had left then summoning her trainers for a debrief.

She spent huge sums buying horses, even more on backing them, often putting on as much as £10,000. Later, when she lived a reclusive life in Chalfont St Giles, floors stacked with yellowing copies of the Sporting Life, she would sleep by day and work at night, telephoning her trainers at all hours. Bookmakers would allow her to bet long after races had finished, trusting her not to have found out the results.

Her greatest horse was possibly the best we have ever seen over fences: Golden Miller won the Gold Cup five times and took a Grand National too.


The face of Irish racing

Cheltenham simply wouldn't be Cheltenham without the Irish, cheering home their winners, celebrating in the Guinness Village and punting fearlessly. In 2010 Ireland was credited with seven winners in the 26 Festival races. Seven winners were trained across the Irish Sea by Irish trainers. But fifteen of the 26 winners were bred in Ireland and twenty races were won by Irish-born jockeys.

The man who sent over the first successful raiding parties and began the Anglo-Irish rivalry was the training maestro Vincent O'Brien who, before he turned to training Derby winners on the flat, won a trio of Gold Cups with Cottage Rake and three Champion Hurdles with Hatton's Grace.

O'Brien was not just a wonderful trainer and a successful gambler. He was an innovator. The broadcaster Sir Peter O'Sullevan says: "Vincent was always far-seeing and that was characterised by him flying his horses over in 1949. So many people said, 'Getting out of an aeroplane and bloody running at Cheltenham?' and wondered what the hell would happen to them but he flew over Castledermot, Hatton's Grace and Cottage Rake."

O'Brien, he says, changed the whole Irish approach to Cheltenham. "Before they couldn't afford to come if they had a potential Cheltenham winner. They just had to sell it. Vincent was the first one who persuaded Irish owners to hang on and have some winners themselves."


The moderniser

Race companies aren't known for their youth policies but Cheltenham proved an exception, appointing Edward Gillespie as general manager some 30 years ago when he was only 27. Eyebrows were raised about a youngster with light-blue suits and flared trousers and the most urgent inquiry made among the doubters was: "Does he wear a hat?"

Hat or no hat, the public school vowels reassured the traditionalists and before they quite know what they have done they found they had authorised another mini-revolution: new stands, a re-sited parade ring and winners enclosure, a cross-country course and a four-day Festival. Gillespie has made reality of Frederick Cathcart's dream but Cheltenham is not only the spiritual home of the sport, it also makes more than half the profits of the Jockey Club, which owns another 13 racecourses. There may be a shrewd commercialism about Gillespie, but the romance of it all has never left the man.

Gillespie buzzes about with relentless energy. On the coldest of days he will be the one man at Cheltenham without a coat as he fizzes between grandstand, office and weighing room sorting out friction over an owner whose tickets have not arrived, demanding the fire be lit in the Hall of Fame, and discussing the going with visiting Irish trainers . "Edward write a biography?," said one colleague on hearing such a project had been mooted by a publisher. "You would never get him to stand still long enough for that, let alone sit."

Robin Oakley is The Spectator's racing columnist and a former BBC political editor. His book, 'The Cheltenham Festival: A Centenary History' is published by Aurum Press (£20) on Tuesday.

To order a copy for the special price of £15 (free P&P) call Independent Books Direct on 08430 600 030, or visit

Have you tried new the Independent Digital Edition apps?
Caption competition
Caption competition
Latest stories from i100
Daily Quiz
Have you tried new the Independent Digital Edition apps?
Have you tried new the Independent Digital Edition apps?
Independent Dating

By clicking 'Search' you
are agreeing to our
Terms of Use.

Career Services
iJobs Job Widget
iJobs General

Recruitment Genius: Clinical Lead / RGN

£40000 - £42000 per annum: Recruitment Genius: This is an exciting opportunity...

Recruitment Genius: IT Sales Consultant

£35000 - £40000 per annum: Recruitment Genius: This IT support company has a n...

Recruitment Genius: Works Engineer

Negotiable: Recruitment Genius: A works engineer is required in a progressive ...

Recruitment Genius: Trainee Hire Manager - Tool Hire

£21000 - £25000 per annum: Recruitment Genius: Our client is seeking someone w...

Day In a Page

Isis profits from destruction of antiquities by selling relics to dealers - and then blowing up the buildings they come from to conceal the evidence of looting

How Isis profits from destruction of antiquities

Robert Fisk on the terrorist group's manipulation of the market to increase the price of artefacts
Labour leadership: Andy Burnham urges Jeremy Corbyn voters to think again in last-minute plea

'If we lose touch we’ll end up with two decades of the Tories'

In an exclusive interview, Andy Burnham urges Jeremy Corbyn voters to think again in last-minute plea
Tunisia fears its Arab Spring could be reversed as the new regime becomes as intolerant of dissent as its predecessor

The Arab Spring reversed

Tunisian protesters fear that a new law will whitewash corrupt businessmen and officials, but they are finding that the new regime is becoming as intolerant of dissent as its predecessor
King Arthur: Legendary figure was real and lived most of his life in Strathclyde, academic claims

Academic claims King Arthur was real - and reveals where he lived

Dr Andrew Breeze says the legendary figure did exist – but was a general, not a king
Who is Oliver Bonas and how has he captured middle-class hearts?

Who is Oliver Bonas?

It's the first high-street store to pay its staff the living wage, and it saw out the recession in style
Earth has 'lost more than half its trees' since humans first started cutting them down

Axe-wielding Man fells half the world’s trees – leaving us just 422 each

However, the number of trees may be eight times higher than previously thought
60 years of Scalextric: Model cars are now stuffed with as much tech as real ones

60 years of Scalextric

Model cars are now stuffed with as much tech as real ones
Theme parks continue to draw in thrill-seekers despite the risks - so why are we so addicted?

Why are we addicted to theme parks?

Now that Banksy has unveiled his own dystopian version, Christopher Beanland considers the ups and downs of our endless quest for amusement
Tourism in Iran: The country will soon be opening up again after years of isolation

Iran is opening up again to tourists

After years of isolation, Iran is reopening its embassies abroad. Soon, there'll be the chance for the adventurous to holiday there
10 best PS4 games

10 best PS4 games

Can’t wait for the new round of blockbusters due out this autumn? We played through last year’s offering
Transfer window: Ten things we learnt

Ten things we learnt from the transfer window

Record-breaking spending shows FFP restraint no longer applies
Migrant crisis: UN official Philippe Douste-Blazy reveals the harrowing sights he encountered among refugees arriving on Lampedusa

‘Can we really just turn away?’

Dead bodies, men drowning, women miscarrying – a senior UN figure on the horrors he has witnessed among migrants arriving on Lampedusa, and urges politicians not to underestimate our caring nature
Nine of Syria and Iraq's 10 world heritage sites are in danger as Isis ravages centuries of history

Nine of Syria and Iraq's 10 world heritage sites are in danger...

... and not just because of Isis vandalism
Girl on a Plane: An exclusive extract of the novelisation inspired by the 1970 Palestinian fighters hijack

Girl on a Plane

An exclusive extract of the novelisation inspired by the 1970 Palestinian fighters hijack
Why Frederick Forsyth's spying days could spell disaster for today's journalists

Why Frederick Forsyth's spying days could spell disaster for today's journalists

The author of 'The Day of the Jackal' has revealed he spied for MI6 while a foreign correspondent