It is the energy of the man that is so striking. Other qualities – presence, wealth, loquaciousness, enthusiasm – come easily to mind as he strides around his Warwickshire estate in mid-morning, mutating seamlessly from horse trainer to city gent. But it is the energy that informs and exhausts.

Robert Waley-Cohen was 62, last time he checked, though he gives the impression of being far too busy to worry about birthdays, let alone those that conventionally signify slowing down. “I don’t think I’m ever going to retire,” he says dismissively.

Plainly, he could have done so by now in ample comfort, particularly since Alliance Medical, the company he founded in 1983 and brought from America to Europe six years later, was sold for £600 million four years ago. Rather than relax with his share of the proceeds, Waley-Cohen seems more hectic than ever.

“What I’ve discovered I enjoy doing is getting companies from the early stages to a certain size. I love that blank sheet of paper,” he beams. “I’m involved with four new-ish businesses now and lots of charitable things, like the National Trust council and mental health charities. I like a vast variety of things to do.”

Yet for one week this month – and specifically, a certain day, a certain hour – even the digressive exuberance of Waley-Cohen will be fully focused on one target, one corner of the Cotswolds, one burning ambition. Or, maybe, make that two. Inside an hour on the final day of the Cheltenham Festival, Waley-Cohen hopes to win the Gold Cup with the most expensive horse he has bought, Long Run, and the Foxhunter Chase with a homebred, Roulez Cool.

That the two races follow one another is, in part, down to Waley-Cohen himself as a Director of Cheltenham. “We felt we were showing great foresight,” he says with heavy irony. “It was always thought that no-one riding in the Gold Cup would be in the Foxhunters, so the winning connections of the feature race could have plenty of time for presentations and interviews. As Sam (his son) is riding both horses and it will be me getting the jockey organised, it could get interesting – but if it is a problem, it will be a very high-class one.”

A similarly delicious dilemma, albeit not quite so fraught in the jockey department, faced Nigel Twiston-Davies last year. While his presence and inner thoughts were being demanded by the national media after Imperial Commander’s Gold Cup glory, he longed to be back in the parade ring legging up his son, Sam, for the Foxhunters he was to win on Baby Run. Twiston-Davies always said the latter was more precious and, though few believed him, Waley-Cohen will appreciate the sentiment.

“I’ll be at least as nervous about the Foxhunter as I will about the Gold Cup,” he says. “I introduced Christies to sponsorship of the race. That was 33 years ago and I still haven’t managed to win it yet! I’d dearly love to win that race above all else.”

It is, too, the strands of family and amateurism that beguile him about the Foxhunters. No surprise, really, as you hear his story. Waley-Cohen is the son of a baronet, Sir Bernard, from whom he inherited many things, but notably a love of the turf. “As an undergraduate at Cambridge, father used to cycle to Newmarket regularly. He was a Flat man and he bet injudiciously.

“He tells a story of visiting his bank manager in Cambridge and telling him he could no longer live on his allowance but that he was going to make a lot of money in business and he wanted an unsecured loan that his father must never know about. Surprisingly, the bank manager backed him on the one condition that he kept his account at whatever branch he might move to. In due course, the manager became very senior and my father became a London director of his bank.

“Father was very involved in the City but he adored Exmoor for hunting. We children went to school in London (Robert attended Eton) but spent all our holidays on Exmoor and that felt like home. We were 1300 feet up and there was nothing to do but ride and hunt. My first racing days were there, at the point-to-points at Holnicote and Bratton Down every May. Father would give me money and tell me it was for punting, not for sweets. We had to back Bertie Hill, Sarah Hobbs’s father, who was a superstar in those parts, and the bookies never seemed worried about taking half-a-crown off an eight-year-old.”

The racing bug was already deep by the time Waley-Cohen entered employment with Christies, the fine art auctioneers. “In 1970, they sent me to New York and I decided to make a diversion to watch Nijinski in Paris. I thought a good bet on him to win the Arc would pay for furnishing my apartment in Manhattan. As we all now know, he didn’t win it, so I ended up rather sparsely furnished!

“For the next few years, I was running all over the States, talking to collectors and looking at paintings, but I missed the riding. I had some friends in Far Hills, New Jersey, who had a horse for sale and I raced him over timber. But I was 24 before I got back to the UK and started riding here. I wasn’t the right shape and I was never fit enough but I had a huge amount of fun. The only race I ever won under rules was a hunter chase at Warwick in 1981.”

Nicky Henderson trained that for him, part of an association dating back 33 years. “It happened by accident, really. George Peter-Hoblyn trained a few horses for me at Manton but then moved to Lambourn and didn’t want to do it any more. George suggested moving my horses literally next door to Windsor House, where Nicky was just setting up.”

Horses were a diversion as Waley-Cohen went about his business life, characteristically making the quantum leap from art to medical supplies. “My two loves were fine art and horses and I decided I didn’t want to make a business out of either. I would love to have made money being a brilliant entertainer or a fabulous sportsman but both were out of the question so I looked for something I could set up and people told me that healthcare was the thing to get involved with and America was the place to do it.”

Cutting a long story short, he went into the provision of CT scanners, still an expensive rarity in the early 1980s, and it took off spectacularly. “You have to remember the internet wasn’t invented then, so I was working odd hours, being based here but running a company in California. What it did, though, was allow me the mornings free to ride and train horses.”

Waley-Cohen took out a permit in 1985 and trained from the stables next to Upton House, the National Trust mansion previously used by the family of his wife, Felicity, as a hunting lodge. Five years later, they had their own house built, surveying a 2,000-acre estate which, as you might expect, is put to many and varied uses.

Even as Waley-Cohen expanded Alliance, transferring the model to Europe with huge success, he never released the tiller on his equine interests. “I’m extremely conscious that I am playing at being a trainer, because I’ve got so many other interests and commitments. The professionals do it all day and think of absolutely nothing else. If I have a really good horse, I will send it to Nicky, though I tend not to have more than two at any one time.”

Breeding, which now fascinates him so much, came later, the motivation a poignant memory. Thomas, the youngest of the Waley-Cohens’ four children, fell ill at ten with a bone tumour. His lower leg was amputated – “though it didn’t stop him playing hockey at school” – and the years that remained were borrowed but precious. “Thomas always had this outlook that if you want to do something, just get on with it,” he recalls. “At the time, if I had money to spare, I always thought I would rather buy a nice picture than an expensive horse. But I had this thought about breeding and I reflected on Thomas’s attitude and thought ‘what are you waiting for?!’

“I decided I would go and buy the best filly I could find and that turned out to be Makounji, now the dam of Roulez Cool. She was too big, really, and she didn’t always do her best but she did win three novice chases one year, including the Pendil. It was also entirely due to her that I ended up with Katarino.

“I like to go to Nicky’s every three weeks or so, to keep in touch and see how the horses have altered – however much you talk on the telephone, it’s not the same. I was down there early in the season to see Makounji and I really liked a little black horse on the gallops. It turned out Nicky had been left with him when a syndicate fell through. Over the next three or four visits, the noises in the yard were more and more positive about this horse until I asked Nicky when he was due to run. When he said November 10, I knew it was meant – that was my 50th birthday. I found a friend to take half, he duly won at Newbury on my birthday and went on to win the Triumph.”

Katarino was to race for Waley-Cohen for an entire decade, albeit being retired midway through with apparently unmanageable injuries. Yet he recovered to win the Aintree Foxhunters twice, with a near terminal attack of colic in between. “It seemed to us a complete miracle. He won twice over the National fences without a race in between and he’d been at death’s door only weeks before.”

By then, the Waley-Cohens had enjoyed another, uplifting Cheltenham Festival win through Liberthine in 2005. “Thomas had died the previous July, ten years after falling ill. Liberthine winning was a terrific lift for the whole family, especially with Sam riding. His instructions were to be very patient, because we knew they’d go lickety-split. Turning the bend at the bottom of the hill he still had ten in front of him but he flew past them all and won by seven lengths.”

Waley-Cohen’s pride in Sam’s jockeyship is natural and powerful but it has been validated by his recent displays on Long Run, especially the exemplary ride to win the delayed King George VI Chase at Kempton. “He’s dedicated, he works very hard at both his fitness and his riding skills. He gets on very well with Long Run and I get pretty dismissive with people who ask if I thought about a different jockey,” the proud father says.

It was a birthday celebration for his eldest son, Marcus, now in charge of the breeding operation in Warwickshire, that took the Waley-Cohens on their portentous trip to Paris in May of 2009. Long Run is a younger brother of two of Waley-Cohen’s previous purchases. “He was a gorgeous horse, he won that day, I knew the breeder and trainer well, so everything seemed right. I had also recently sold most of my shares in Alliance, so for once in my life I had money in the bank. I slightly gasped at the price but my wife said: ‘This is what you love, you’ve got the money, go ahead and do it.’”

There has been no cause for regret or recrimination – not that Waley-Cohen seems to deal in such unhelpful currencies. Long Run is heading for the Gold Cup as second favourite and, judging by the fan mail that keeps landing on the family mat, as a horse of soaring popularity.

For his owner, the confluence of his two best horses on the final day of this of all Festivals is so timely you suspect he planned it meticulously years ago. Two months later, Waley-Cohen will succeed Lord Vestey as Chairman of the racecourse that inspires dreams in every jumping soul.

“I’d stewarded there from 1980 and been involved on the board for 25 years,” he relates. “We’ve had 20 years of growth and development under Sam. The buildings masterplan hasn’t been completed yet and it’s very much my intention that we will do so and provide better facilities. We’re very lucky, though, that everyone aspires to Cheltenham. It is our Olympics, everything is on the road to the Festival. I’m a very lucky owner this year – I would just rather my entertainment was spread out a little more!”

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In bloodstock matters, Robert Waley-Cohen is a dedicated Francophile. Most of his purchased horses are bought in France, three are currently trained there and he has a high regard for the French system of developing young jump horses.

“One of the big problems in Britain is this concept of being a novice and then not a novice,” he explains. “In France, they have specific programmes for three- and four-year-olds. You might be running against the best of your generation but you are not up against the rest of the world.

“Their races are also run in a different style, a much steadier pace than our races. It’s kinder on young horses than our pillar-to-post instinct. I also think that the French hurdle is a much better introduction to a steeplechase fence that the English hurdle.”

Waley-Cohen has used his position as Chairman of the Point-to-Point Authority to instil such values in British amateur racing. “I’ve tried very hard in the point-to-point world, introducing four-year-old only races.

“Going further than that is difficult. The French have different fences for young horses than for all-aged championship races – it’s not as formidable a course. But I don’t think many British racecourses could even contemplate having separate tracks.

“If I have horses that are precocious enough, I break them at two and get them trotting over poles, then send them to France with a view to their three-year-old programme. The prize-money is very steeply staircased, so the top races in Paris get huge money. I know Long Run was at the top of the tree but he came back here having won €700,000 – that’s a staggering amount of money after 12 races.