Fur coats, Bentleys and bus passes: meet the flamboyant former king of the betting jungle

In this article first published earlier this month exclusively for Racing Post Members' Club subscribers, senior features writer Peter Thomas talks to legendary on-course bookmaker Stephen Little. This has now been made free to read for users of the Racing Post app as our Sunday Read.

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Stephen Little used to be a bookmaker, but not just any old bookmaker. Even when the betting ring was in its considerable pomp, he was still the one that stood out, flamboyant yet never flashy, striding from his brand new Bentley in his full-length fur coat to his pitch on the rails, where he quietly yet confidently stood his ground at the biggest meetings, inviting the most fearsome of punters to duel with him for heavy six-figure stakes.

From unlikely and often impecunious roots, this low-key leviathan lifted himself up, as the title of his autobiography suggests, from bicycle to Bentley. When a pushbike was all he could afford, he pedalled inhuman distances in wind and rain, from Newton Abbot to Cartmel to Perth and back again, staying at youth hostels to ease the burden on his wallet. When his mathematical genius and unflappable temperament prevailed on the racecourse, he became accustomed to travelling in rather greater style.

Now, though, Little's world has turned full circle. "I was thinking about calling the book From Bicycle to Bentley and Back Again," confesses the 77-year-old ("I call it 65 plus VAT"), in between singing the praises of the senior citizens' bus pass, to which he is now a grateful convert.

In the hallway of his house stands the bicycle he uses to trundle around town on. The Bentley has long since gone, bought new in 1990, traded in 28 years later as a down payment on his wife's car, which he uses occasionally when his bus pass and railcard won't cut the mustard. Even the fur coat has fallen prey to the moths.

If you were beginning to feel sorry for him, though, may I suggest you dry your tears and put the violin back in its case, for Stephen Little is not on his uppers, nor even close to it. The financial good sense that saw him thrive on the racecourse made it a certainty that he'd eventually come to embrace the value of free travel on public transport, but it's much more a welcome bonus than a financial necessity.

The Bentley, meanwhile, was surrendered without mourning. "I was never much of a driver," he says. "It was a nice car, but a lot of the time one of the staff would drive me home from the races while I sat and calculated how much we'd lost."

The bicycle in the hallway? Well, when I tell you the hallway sits behind the rather distinguished front door of one of the most desirable houses on one of the most sought-after streets in the country – the stunning Royal Crescent in the heart of Bath – then you'll begin to understand the degree to which Little does not require our sympathy.

While Bath, with its substantial hills, may not be ideal cycling territory for a septuagenarian – this year was the first in living memory that he didn't make the ride out to the city's racecourse, the highest in the country – he persists, not because he can't afford the diesel but because he loves it and, anyway, he doesn't want to get himself an electric bike, "because that would be admitting I'm getting old".

It may be a case of stubbornness getting in the way of ease, but all in all, Little's is not a bad life, and it was all bought and paid for by a remarkable career in racing.

"I just set out to be a surviving bookie": Stephen Little outside the magnificent Georgian house he calls homeCredit: Edward Whitaker

'I was wounded, but not fatally'

Under the triple-height ceilings of his Georgian mansion, the Lincolnshire vicar's son can reflect with pride – after brief moral disputes with his father, followed by valuable support – on the rewards of several decades of balancing prudence and boldness in an environment where many have found it all too easy to lose their equilibrium and teeter into the abyss.

When he talks, almost casually, of bets like the £210,000 to £120,000 he laid on Sound Man (finished third at 11-8) in the 1996 Champion Chase – and others in his ledgers he can't even remember the outcome of – it's hard to fathom how, in the next breath, he can claim to have been a model of restraint and economic good sense. He'll confess that even he got carried away on what he describes in the book as "one of those 'I was there and I wish I hadn't been' days", but even that experience he puts down to sound financial reasoning, albeit frayed by chaos and mayhem.

So, was he a fearless gambler or an unflappable accountant? A swashbuckling cavalier or a human calculator? We know he was a mathematical genius – his prize-winning days at Uppingham tell us that – but if betting was just arithmetic, surely the ring would be full of wealthy academics.

"I certainly wouldn't say I was risk averse," he says, on the brink of being offended, "but I preferred to take the risks I could afford to take. I didn't set out to be a top bookie, I just set out to be a surviving bookie, and I can't help feeling that some bookmakers took risks they couldn't have met if things had gone wrong.

"We don't know about the ones that did go wrong because they just faded away, which is why I say you never see a poor bookie, because by the time they're poor, they're no longer a bookie. There were a few that made a splash and then 'knocked' in the end, but I was always in it for the long run."

By the time Frankie Dettori took Ascot by storm on that cataclysmic day in 1996, Little was a well-established layer with a proud reputation, but he wasn't immune from the suffering. Yet if that afternoon proved anything, it was that while even a good bookie can be hit hard, the very best have the wherewithal to recover from the mauling.

"They call it the Magnificent Seven," he deadpans. "I call it the Malevolent Seven, but it was a tempting situation. If you can lay a 12-1 shot [like Fujiyama Crest, winner number seven] at 9-4, then you want to do it, and keep doing it.

"I didn't have that much control over my liabilities because it was just too busy, but the big firms would have had far less, and they couldn't have known what was happening in all their shops. So, the phones were quite busy by the middle of the day, and about three races from the end, bookies were ringing up and having doubles or trebles with me to limit their liabilities.

"Make no mistake, I wasn't hit as badly as some, but I don't remember the day with fondness. I was wounded, but not fatally."

'The fur coat made me well known, which was important'

In the hallway, framed tidily and hung neatly in rows, are the racecards, meticulously preserved, of Little's first visit to each of the country's courses. Some are the lingering curios of tracks long since defunct, while the symmetry is interrupted by recent inconvenient arrivals like Great Leighs.

He admits to keeping all his racecards, along with all his betting ledgers and diaries – "so I didn't have to dredge the memory too much when I was writing the book" – and to being "meticulous" by nature. Even his 'unique selling point' as a rails bookmaker, the aforementioned fur coat, started out as more of a practicality, although it soon turned into a valuable trademark.

"It kept me warm when I was standing out in the cold all day, which was the main object," he insists. "I was a bit self-conscious wearing it at first, and people thought there might be some connection between the coat and my sexual preferences, which there wasn't, but it soon made me well known, which was important when you were betting on the rails in the days before boards, and even now people ask about it.

"Sadly it's gone, so these days, on the rare occasions it gets cold, I just retreat to the bar."

It's a fine example of the combination of good sense and opportunism that stands a bookmaker in good stead, but Little, while happy to promote himself sartorially to gain custom, never lost sight of the golden rules that he made early on in his career.

"It's very precarious and easy for it to go wrong if you're not careful," he cautions, as if to remind himself, even now, "but the three decisions I made early on were right: to bet to figures rather than opinion; not to chase money if it didn't come – don't go over the odds, because that's a quick way of getting into trouble; and not to cut people back. If they wanted a big bet it would be better to take it, even if I did have to hedge it at a shorter price."

It's a betting mantra he's never forgotten: the need to do business, and plenty of it, but never to forget to do it on businesslike terms. Just because he was keen to take on the biggest players, it didn't mean he had to abandon first principles.

"I stuck to those rules just about through my career," he says proudly. "Of course I formed opinions but I learned to ignore them [the book recalls the dismissive approach he took to those "mugs" taking 20-1 against Michael Dickinson training the first three home in the 1983 Gold Cup], and concentrating on the figures allowed me to build up a reputation for laying reasonable bets, which got me known."

Little at Wincanton races in January 1999: he priced the whole field in the fifth race at evens in protest against those administrating the betting ringCredit: Edward Whitaker

'There were debts I knew would never be paid'

Back in the day, getting known for laying reasonable bets meant that before too long you'd come face to face with the big fish – sharks, some might call them – and have to decide whether to stand your ground or politely decline.

Little was never one to turn down good trade, and that meant seeing the whites of the eyes of Michael Tabor, JP McManus and Barney Curley. These were not punters to be taken lightly, but with the right mindset, the clashes were to be made the most of.

"They were by no means mugs and I never felt I was taking them on, as such," he explains, "but they helped to boost turnover and once I'd laid a bet to them, it really got me going in a race. I just had to make sure I had my prices right and my staff were ready to spring into action.

"I always assumed they were very well informed but I didn't let that bother me too much because for me it was always all about figures, and one advantage of betting with people like that was that I didn't have to worry about how long it would take to get paid."

Little shrugs when he recalls the string of bad debts that remained unsettled when, disillusioned by bookmaking politics and the decline of the ring, having sold his pitches to Corals and become quickly unimpressed by working for them as an on-course representative, he retired from the game.

Luckily, by then he had acquired his palace in Bath – bought 30 years ago for £720,000, he recalls – and retained his quietly philosophical approach to life, which continues to serve him well.

"There were debts I knew would never be paid, by nasty and spiteful people [names redacted] whose only ambition in life seemed to be to put one over on a bookmaker," he says, "but if I'd made the decision early on never to give anyone any credit, then I don't think I'd have got anywhere, because on the rails without a board, you need customers."

He confesses to lacking confidence in racing's future, at a time when affordability checks are being insisted on by "people with no background in gambling" and public interest in the sport is in steady decline, but he still goes to the track a couple of times a week and works from time to time for a local on-course bookie. He's underwhelmed by the homogeneity of prices in the ring, though, and often prefers to "fiddle around on Betfair", going to the betting shop seemingly only to remind himself what a frustrating, innumerate and restrictive place it can be.

"The gambling's not important," he concludes. "It's about keeping the brain ticking over more than the money itself, but I was looking for an 'arb' recently and asked for £60 on a 6-1 on shot in a football match, which I didn't think was terribly ambitious, and they said I could have a tenner.

"That's fine, though. I was a much better bookmaker than I am a punter, anyway."

He was always much more than just a fur coat and a Bentley, that's for sure, although he makes no great claims for his career, apart from a cautious offering that seems to undersell the man himself and the Georgian grandeur that surrounds him: "I'm quite proud of the fact that I started out with nothing and finished up with something."

From Bicycle to Bentley, a Bookmaker's Story, by Stephen Little, is published by Pen and Sword White Owl, £20.

More Sunday Reads:

Patrick Mullins: We came, we saw, we left with our tails between our legs - but I've never seen anything quite like it 

Adele Mulrennan: 'My heart was pounding and my mouth was dry - I was so nervous' 

Davy Russell: I used to go home to bed and sleep for an hour after riding out - that's time I should have been using to upskill 

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