When you can look out through French doors at the splendour of Stetchworth Park Estate, as Bill Gredley can, you are entitled to see the world on your terms.

The man who came out of London’s war-torn East End in the 1940s has made his own way through life. He has accrued several fortunes, ruffled as many feathers and consistently aroused comment by his penchant for unorthodoxy. Often to be seen with a smile on his face, he can surprise people by his occasional bouts of vehemence.

To enter his fiefdom in Stetchworth, three miles south of Newmarket, brings another surprise. Two statues, a pair of bears at least 12 feet tall, patrol a driveway that leads to the main house, where an equally arresting figure of Geronimo greets you. The Apache talisman is cast aboard his horse on a near-vertical descent, as if he had just jumped Becher’s Brook hard against the inside rail.

Once inside, you are ushered into a boardroom where colour threatens to explode from walls overladen with strikingly vibrant paintings. No two of them are alike. The odd classical landscape apart, it is a collection of polar extremes that probably reflect the diversity of their owner’s mind.

In one corner, wine flutes strewn randomly on a wooden table are reproduced with remarkable purity on canvas. Subtle shades of light and dark trace glass curves so faithfully as to be redolent of acclaimed photography. Next to this hangs a morass of colourful, particularly corpulent faces in near-caricature style.

“I commissioned this Polish artist to paint 100 of the ugliest faces he could possibly imagine,” Gredley, 83, says with a smile. “When I look at it, I try to match the faces with those of well-known people, or people I know. I can see Gaddafi in there.”

Not long after I started having horses I realised how little I knew about it. In the 1970s Clive Brittain asked me to take two horses back to my farm for a rest, a colt and a filly. I turned them out in the same paddock and they had a terrible fight

Mischievously, he points out other doppelgangers that would be manna from heaven in the hands of a muck-raking journalist. But that’s Gredley in a nutshell. As he concedes later: “I’m very prone to doing things on the spur of the moment.”

This summons another contrast within the man himself. The lure of spontaneity does not square with the layers of patience required to own racehorses, never mind breed them, as he has done at Stetchworth Park for 40 years now.

Big Orange is one of Gredley’s stars

The first top-class horse he bred and raced was 1991 Eclipse Stakes winner Environment Friend. The grey was followed a year later by User Friendly, who won three Classics before she surrendered her unbeaten record by a scant neck in the 1992 Prix de l’Arc de Triomphe. In Big Orange, Gredley now has another homebred to point at the big races – starting with the Gold Cup at Ascot.

He admits to making mistakes, and plenty of them. He didn’t see why Environment Friend should retire from racing when the horse took up stallion duties: after the Eclipse he ran 24 times over four seasons without winning. And for a brief spell in the early 1990s he had his horses trained at Stetchworth Park Stud. His desire to challenge convention became evident.

“Not long after I started having horses I realised how little I knew about it,” he reflects. “In the 1970s Clive Brittain asked me to take two horses back to my farm for a rest, a colt and a filly. I turned them out in the same paddock and they had a terrible fight.

“But the most wonderful thing about breeding horses is learning about it. It takes me completely away from my other businesses. I find it so relaxing.”

Gredley’s affection for horses spawned from the formative years he spent living with his grandmother. He arrived there by a circuitous route.

“I was born in the East End of London,” he starts. “Father was a dock worker, mother was as Irish as the day is long. I was evacuated at the start of the war, aged six, to Wales. I was on my own with a load of other kids and had a label on my shoulder with my name on it.

“I was put with a miner; wonderful people he and his family were. Then my father brought me back to London during the Blitz. Well, we were bombed out of our house so we went to my grandmother in Essex, where I stayed until I was 17.

“That was the first time I came into contact with horses, which were ponies that belonged to the gypsies. Big fat things, they were. They never ran anywhere, they walked the whole time. I used to look at them in wonderment.

“I went into National Service and was sent to the Air Ministry, where I served at an American base in West Drayton. One of the officers there was an Air Commodore, a bomber pilot who flew an Anson.

“He was a racing guy and he took me up in a plane over Bath racecourse. I was fascinated. At that time I didn’t know what a racecourse was!”

These would have been merely anecdotal memories had Gredley not made his fortune in the property business through his company, Unex. A regular fixture in any ‘Rich List’ compilation, he soon had the means to get involved with racing and breeding.

I know it wasn’t the done thing to go racing wearing a ponytail but I don’t know why it aroused such a lot of comment. I suppose it was because you weren’t conforming

“I did some deals, made some money,” he says. “I had offices in Mayfair for 25 years and one day I decided to move it all here to Stetchworth. We now have 30 people working here, most of whom came with me from London. It has changed their lives.”

Even then, however, Gredley’s engagement with the sport came on his terms. He would often arrive at the races bereft of a tie and a long ponytail tumbling down his back.

“That ponytail business seems to have stuck with me,” he reflects. “I know it wasn’t the done thing to go racing wearing a ponytail but I don’t know why it aroused such a lot of comment. I suppose it was because you weren’t conforming.”

The origins of it were innocuous enough. He was holidaying in Acapulco when his hair had grown longer that he would normally keep it. “When I got out of the swimming pool I’d borrow one of my wife’s hairbands to tie it up,” Gredley recalls.

“A friend said to me I’d never turn up at Royal Ascot looking like that, so we had a bet, and I did it.”

What he didn’t know at the time was that people high up in Ascot’s chain of command debated whether he should be asked to leave.

He can’t remember when the ponytail was shed but he can remember the circumstances. “I’d been to a party with my late wife Sarah [who died of cancer in 1992] and when I woke up the next morning I found the ponytail in my hand,” he says with a smile. “Sarah had cut it off in the night.”

At that time Gredley thought nothing of standing up for what he believed were inequalities or injustices within the sport. He provoked a furore in 1992 when he advocated an owners’ strike to highlight shortcomings in racing’s financial relationship with bookmakers and the pedantic pace of change that saw the Jockey Club eventually hand over much of its power to the newly-constituted British Horseracing Board (BHB).

Those unwilling to rock the boat described the strike as an idle threat, although Gredley’s recollections illustrate how much progress he had made.

“I talked to a lot of politicians at the time,” he says. “Douglas Hurd, the Home Secretary, kept telling me racing and bookmaking had to sort out their own differences without troubling the government [with a referred levy settlement].

“Peter Savill was around at the time; he was a rough diamond who I got close to because he wanted to see change as much as I did. I tried to set up a BHB of my own. I had Peter Middleton, then Chairman of Barclays Bank, lined up and some other important people, but then the BHB got up and running. It sorted itself out.”

It was the sort of behaviour that led to Gredley being described as a maverick. “I prefer the word eccentric,” he says.

Doesn’t maverick fit him better? “What does maverick mean, exactly?” he replies.

To the dictionary’s promptings of individualism, non-conformism, free-spirited, unorthodox and unconventional, Gredley smiles and says: “Okay, then I’m happy to be called a maverick.”

Although he might have disputed the choice of word 25 years ago, Gredley is far less concerned with such matters now. He still brings a formidable business presence to the boardroom – leopards don’t change their spots – but the time has come for him to smell the roses.

His favourite rose garden is his horses. “I get as much enjoyment from them as I always have,” he says. “I was travelling everywhere on business in the US, South America, Germany, France. One day I came back home, got in among the horses and realised I’d had enough of the commercial world.

“I didn’t think that would ever happen, but it did. I’d be very surprised if the same thing ever happened with the horses.

“I continue to make mistakes, we all do. I might have done things differently when I started had I known then what I know now, but what I love is that it is a great leveller. You spend all that time and money, and when your horses get to the racetrack they can’t even pick their legs up.”

User Friendly was one that could. Her rampage throughout the 1992 season saw her win the Oaks, Irish Oaks and St Leger. She was, quite simply, the horse of a lifetime.

User Friendly and George Duffield see off All At Sea and Pat Eddery in the 1992 Oaks

Before User Friendly ran as a four-year-old, Gredley sold half of her to Gary Tanaka, who raced predominantly in the US. There was a tug of war over where she should be campaigned but Gredley prevailed in keeping User Friendly in Europe, where she won the Grand Prix de Saint-Cloud from five starts in which she never rescaled the heights of her Classic campaign.

“At the end of that year Gary bought the other half and sent her to California,” Gredley recalls. “It didn’t suit her; she only ran twice and didn’t do much. Afterwards I felt very sorry to have let her go. There will always be an emotional attachment.”

When User Friendly retired Tanaka sold her for $2.5 million at Keeneland in 1995, after which she went to Japan. From there she returned to Keeneland four years later and was bought by David Nagle for $1.7m.

For Gredley, however, living embodiment of User Friendly takes the shape of her unraced half-sister, Friendlier, whose three daughters, Beyond Fashion, Madame Defarge and Unex Mona Lisa, are also among the 18-strong broodmare band at Stetchworth. The best of them was Madame Defarge, a winner who ran third in the Listed Pretty Polly Stakes for Michael Bell, the latter one of seven trainers Gredley patronises with around 30 horses in training.

A pair of three-year-olds to receive favourable mention are Peru, trained by Hugo Palmer, and Dwight D, with William Haggas. In doing so, however, Gredley expects very little. “Today’s swans are tomorrow’s geese,” he maintains.

It says a lot about Gredley that he can make the assertion at all. It’s a long way from the land of the Queen Vic to the 450-acre Stetchworth Park estate he bought from the sixth Duke of Sutherland. But he has never wanted to shed his roots.

“I have found that you can’t do that even if you wanted to,” he says. “That pleases me. My [six] children are growing up in a totally different world to mine and the one thing I would like to see in them is a bit of humility.

“I have made a success of many things I’ve been involved with. People might have laughed when I told them how I intended to do something, but I think I was entitled to my view. It hasn’t done me too badly.”