A public-school-educated son of a vicar, softly spoken, articulate, but known for great mental toughness, Little's background is a world away from the market-trader backgrounds of most British course bookies.
'My fi rst big wins were at prep school in Newark,' begins Little, as a chill, winter drizzle falls on Cheltenham. 'Someone else had grabbed the book on the Grand National, so I took the Lincoln at Doncaster). We weren't allowed to have any money at the school, so all bets had to be in sweets. I always had a good feed.
'Later, at Uppingham School, I continued my run of form and started to go racing with a friend in the school holidays. Everyone thought I was mad to want to be a bookmaker, but I felt then and I still feel now that I've been lucky to have something I was that interested in.'
Little left school at 16 and, for the two years until he could take a legal bookmaking job, acquainted himself with most of Britain's racecourses - often by cycling there. At 18, he finally started work in an offi ce, only to quit within months to bet on major hare coursing event the Waterloo Cup, Bristol dogs, various point-to-points and the odd Silver Ring.
No small feat
Living proof of the old maxim 'a bad day at the races is better than a good day at the offi ce', he secured his first big racecourse job working on the rails for various bookmakers including Thomas Henry Dey. Next came the acquisition of his own rails pitches next to contemporaries such as John Banks and John Pegley.
'It was almost impossible to get a board pitch in those days,' explains Little, 'but getting a rails pitch was much easier. The company was interesting, too, even if at quite a few of the smaller courses there were just me, Hills, Ladbrokes and a few locals.'
Such talk of 'smaller courses' is typical Little self-effacement, as it certainly isn't for the minor meetings that he's known. More than anything, it's for his infallible nerve in taking on major-league, six-fi gure punters such as JP McManus, Nigel Taybrook and Johnny 'Lights' Hurndall at courses such as Cheltenham. Straight after today's fi rst race, we test the limits of his discretion.
'I don't like talking about who bets with me,' he replies, slightly pained, 'but I can mention JP McManus, I suppose, because it's well documented. Yes, I suppose some of our meetings were legendary. Yes, yes. [His wry smile and glinting eye at this point say infinitely more than his words]. But let me tell you something: I certainly felt fear. Yes, you could say it was certainly exciting when he was around!
'As for Cheltenham itself,' adds Little, 'it's a special place and I always love coming. I've probably had more good meetings than bad over the years, but I've never felt immune from losing. I certainly never had as bad a Cheltenham as the bookies had a couple of years ago. That said, one Cheltenham I worked in the 1980s, the first day was twice as bad as the previous record. The second day was also worse than the previous record. On the third day, the clouds lifted and I could virtually write my own results. I think I finished just behind on the week, but I'd been in such a hole it felt like I'd won a million pounds - even better than when I won my biggest single bet of £70,000.'
Taking it on the chin
Little's biggest career hit as a bookie, of course, was working on the rails as Frankie Dettori rode Fujiyama Crest to complete his 'Magnificent Seven' day of winners on 28 September 1996. Silky Stephen may not have lost the million pounds that ensured Gary Wiltshire became Britain's most infamous bookie overnight, but he did enough phone business to ensure - in classic understatement - that he 'wasn't very pleased' when Frankie went past the post. Pushed further, he even admits finding it 'exhilarating' even though he was 'a bit sick at the end.' When most bookmakers would have collapsed in a fit of effing, blinding and despair, it's hard not to imagine Little retiring to the bar, pouring a pink gin, fixing his tie and reaching calmly for the next day's fixtures. Let's not forget that we're talking of figures allegedly in excess of £500,000...
Smack your pitch up
The days of Little taking on punters at Cheltenham are long gone. While Stephen hasn't strictly retired, he sold his racecourse pitches to Coral in early 1999 and joined them, only to be made redundant a couple of years later.
'I gave up the pitches because that year the National Joint Pitch Council (NJPC) regulations were coming into play and I felt they didn't know what they were doing,' explains Little. 'I think I was subsequently proved correct. Expenses are higher and there's a lot less money about, partly because of the exchanges. But the NJPC let in too many amateur bookies who lost money, and it's very difficult to compete with people who don't need to win. Needless to say, most of the amateurs disappeared quite fast.'
Interestingly, Little is one of the few course bookmakers not to have harsh words for betting exchanges. He explains: 'I don't think exchanges as such are the problem. It's the lack of tax differential. A few years ago, if you were a serious punter, you had to come to the races to avoid tax and shop around for the best prices. Now if you're serious, you sit at home on the internet and look at the offers. It's sad, but I guess that's evolution. Still, there's a good crowd here today.'
There is, and a buzz that no armchair punter is going to get legally in his living room. Little, who still goes racing at least two or three times a week, agrees.
'There's really nothing like live racing. And there's nothing like the variety in British racing. We don't have enough racecourses in this country. When I was younger, I visited every single British course on my bicycle. I still love racing so much that I occasionally still cycle to a meeting from my home. Maybe not quite to Perth any more, you understand, but the passion is still there.'
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