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

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.

FREDERICK CATHCART

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.

DOROTHY PAGET

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.

VINCENT O'BRIEN

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."

EDWARD GILLESPIE

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 www.independentbooksdirect.co.uk