There are certain people in life with whom you can tag the letter ‘y’ onto their surname and it becomes, for all intents and purposes, their accepted name.

In sporting terms around here, one-time Cheltenham Town football captain Chris Banks was always known as Banksy, former Gloucestershire cricketer Martyn Ball answered to Bally and if you talk about Teaguey, everyone knows you are on about Gloucester rugby legend Mike Teague.

The addition of the ‘sixth vowel’ is a term of endearment, an appreciation of that individual’s personality and, in these cases, their sporting prowess in their chosen field.

Out in the Cotswolds and beyond, if you’re talking about a chap called Webby, particularly in the racing fraternity, it’s a fair bet that they’ll know you’re discussing Allen Webb.

You see, Webby was a decent jockey back in the day, someone who rubbed shoulders with the likes John Francome, Peter Scudamore and Jonjo O’Neill, racing greats all three of them.

And since retiring from the saddle some 25 years ago, Webby has remained very much part of the racing industry, as both a saddle maker and a valet for some of the top National Hunt jockeys of today.

Webby was born in Leamington Spa in 1956 and his earliest memories of life in this regency town in Warwickshire less than 30 miles from Stow-on-the Wold are happy ones.

“I was a member of St George’s Boys’ Club,” he said. “It was run by Fred Churchill, he was a brilliant bloke.

“We’d play table tennis, play five-a-side football, go fishing, we’d go on trips.”

And it was on one of those trips that Webby’s life was shaped, a life that saw him clock up close on 300 winners as a jockey, including a couple at Cheltenham Festival, before carving out a successful business career.

“Fred Churchill took us to Butlin’s,” Webby recalled. “It was at Minehead and I went on a pony on the beach and the bloke who was leading me said, ‘You should be a jockey’.”

Webby was only 12 at the time but those five words struck a chord and not much more than a year later he began a five-year apprenticeship with top trainer David Nicholson, who in those days was based at Condicote, near Moreton-in-Marsh.

“I didn’t want a life in a factory, I didn’t feel like factory fodder,” he explained. “I remember seeing the careers officer at school and telling him I wanted to be a jockey and he just said, ‘Next please!’”

But Webby was determined to pursue his dream

“I left school when I was 13 – I was a year up because I was born in August – and went straight to David Nicholson’s,” he said with a chuckle.

“I was a 4ft 6in, four-and-a-half stone apprentice jockey. He sent me off to buy a suit and I had a 24in waist and a 24in leg.”

At his size back then Webby appeared tailor-made for a career as a Flat jockey. However, he soon put on a bit of weight which meant his future lay in National Hunt racing, although at that stage of his life he had more everyday concerns to consider.

“When I first became an apprentice there were 13 of us living in a three-bedroom cottage,” he explained, before adding with a laugh, “and the head lad had a room to himself!

“We’d work 13 days out of 14, including bank holidays. If you were riding on a Monday, you had to ride-out on a Sunday on your day off.

“We’d get two weeks’ holiday a year and were paid £1 a week.

“It was hard at the time but good fun. I was very, very fortunate, I was in the right place at the time.”

Webby is being a little modest there. Although his weight meant he could claim an allowance, he was still the only one of his 13-strong apprentice jockey intake who made it as a professional rider.

His first ride under Rules was for trainer Derek Kent, who was based in the south of England.

“He was much thought of as a trainer, he set me on my way,” said Webby.

And he didn’t have to wait long for his first winner, coming as it did three months before his 20th birthday in May 1976, although Kent wasn’t the trainer.

“It was on Vale Royale at Stratford for George Hackling, a small-time trainer from Prestbury,” recalled Webby. “It was my fourth ride over jumps.”

That first win is a special moment for any wannabe jockey, of course, and although the post-race celebration was modest, it was, nonetheless, very special for the 19-year-old Webby.

“My dad had a mate at the course and he told him I’d won,” continued Webby. “Dad couldn’t be there but when I got home I had a drink with him, that was special.

“I owe my parents everything, they let me do what I wanted to do, they let me follow my dream.”

Webby speaks very warmly of the many, many people who have had a big influence on him over the years.

He is an easy man to talk to and is proud of the many friends he has made in racing.

And he remembers those early days as if they were yesterday.

“David Nicholson was hard but fair,” he said. “I don’t regret it for a minute, I made a living out of being a jumps jockey for 20 years.”

Webby didn’t actually ride that often for the man who was always referred to as ‘The Duke’.

“When Robin Dickin and John Southern lost their claim I was next in line,” said Webby. “And then when I lost my claim others came through.”

By then he was already establishing himself as one of the better jockeys around and he came of age when as a 21-year-old he won the Grand Annual Chase at Cheltenham Festival aboard the Derek Kent-trained Young Arthur in March 1978.

“Derek Kent was one of the best trainers,” said Webby, “he was a master. I was a 7lb claimer so it was very brave for them to put me up,” before adding, “but it was all down to the jockey!”

Webby can still remember the roar of the Cheltenham crowd when he crossed the finishing line – Young Arthur was well backed – but that wasn’t the case when he rode his second winner at the greatest jumps festival in the world.

That was four years later in the Daily Express Triumph Hurdle.

“I was riding Shiny Copper, a 33-1 outsider, for Dina Smith,” said Webby. “I think I was fifth choice jockey, everyone else declined the ride or wasn’t available.”

And Webby was certainly pleased he took up the challenge.

“It was great,” he continued, “it was one of my best winners. I was under no pressure, everything just opened up for me.

“When I crossed the line I think the only bloke clapping was my great friend Roy Mangan, who had a trade stand at the course. Everyone else was drowning their sorrows!”

Webby rode some half-a-dozen winners across all meetings at Cheltenham over the years and also experienced the thrill of riding in the Grand National at Aintree.

That was on 50-1 shot Queensway Boy in 1989 and Webby said: “We completed a circuit but we’d both had enough when he refused at the 19th. I got round the Topham though.

“I also won three Nationals – The Midlands, Swedish and Jersey Nationals, I had a great time.”

That Webby enjoyed his riding career is very obvious.

“When I was a jockey we used to have the summer off,” he said. “I’d go off riding in Scandinavia, I loved it. I rode all over, in Germany, France, Italy, Jersey and Guernsey.”

Webby has so many special memories – “There’s nothing better than making a living out of sport,” he says – but inevitably there were down times as well.

Typically, Webby is able to make a joke about them.

“I had about as many broken bones as I did winners, it was part of the job,” he said. “I broke my neck, I broke my jaw two or three times – I remember one year eating my Christmas dinner through a straw!

“Most of my teeth are around Worcester or Nottingham racecourses. You came to expect the injuries but I was lucky, I had no lasting injuries.”

He retired from race riding at the age of 38 and these days runs a very successful business – Mangan and Webb Saddlery – which is based in Stow.

“We make the lightest racing saddles in the world,” said Webby with obvious pride. “They’re made out of carbon fibre and weigh 11oz. AP McCoy used them throughout his career and Richard Johnson uses them now.”

Webby, who lives in Bourton-on-the-Hill just outside Moreton with his wife Boni, enjoys his job as a valet as well.

He’ll be at this year’s Cheltenham Festival tending to the likes of top jockeys Aidan Coleman and Paddy Brennan, although he admits that he prefers the smaller meetings since hanging up his stirrups.

“When you go to the really big meetings – Cheltenham and Aintree – it makes me realise that I can’t do it any more, I’m too old,” he said. “I can’t even ride out now.”

And while age catches up with everyone, he can at least still ride a motorbike, which is one his other great passions.

“I’m just about to buy a new bike,” he said with a laugh. “I had a 959 Triumph but it got a bit too heavy for me. It fell over and I couldn’t pick it up!

“I’ve got permission from Boni to get another one.”

He’ll enjoy that, too, just like he’s enjoyed every moment of his life in National Hunt racing.