Wiltshire’s magnificent loser
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Best and worst sports bets ever - Wiltshire’s magnificent loser
Frankie’s 7 Winners At Ascot…
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Every week, bookmaker and former Racing Post chief sports betting writer Mark Worwood takes you inside the wagering industry with tales of the best and worst bets of all time.
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Successful long-term punting is all about betting when the odds are in your favour. A losing bet is not necessarily a bad one, just as a winning bet is not necessarily a good one. After all, anyone can back a heap of winners at 1-10 but, unless the true probability exceeds 90.9 per cent, one is going to end up with a bloody nose in the long run.
As far as I am concerned, one of the best sports bets of all time was a loser and a famously expensive one at that.
It was Saturday 28 September 2025 and the prospect of a trip from my Surrey home to see Walsall play Bury in the third tier of English football was unappealing, particularly after painting London town red the night before, first with some Racing Post colleagues and then some old university mates.
So I plonked my sore head in front of the television and put on the radio for more sports information. There was a good day’s horse racing in the offing at Ascot but little did I know that the day would go down in the sport’s history.
Things started to get interesting just after four o’clock and not because my beloved Saddlers had established a 2-1 lead over the Shakers thanked to the second best footballer ever to come out of Bermuda, Kyle Lightbourne. In case you are wondering, Shaun Goater was the best. Feed the Goat and he will score, as Manchester City fans used to sing before they had the millions to spend on global superstars.
The afternoon was turning into one to remember because the punters’ pal, Frankie Dettori, had ridden the winners of each of the first four Ascot races, only one of which had been a favourite. Dettori was booked to partner Fatefully and Lochangel in the fifth and sixth event respectively and both of them were forecast market leaders. Fatefully landed odds of 7-4 in the fifth race and Lochangel, racing in Jeff Smith’s colours made famous by sprinter Lochsong, made all to win the sixth race at odds of 5-4. Half a dozen races gone and Dettori was on a six-timer paying 8,364.5-1.
Frankie Dettori (Photo credit: Wikipedia)
Sports broadcasters stopped dissecting the day’s football results – Walsall won 3-1, thanks for asking – and turned their attention to Ascot where Dettori was getting ready to ride Fujiyama Crest in a two-mile handicap. The Italian had partnered the son of Roi Danzig three times before, winning on him twice, but he was not one of the major chances, at least according to the tissue prices framed that morning.
With all of the High Street bookmakers realising that they had massive liabilities on Dettori – having worked in a licensed betting office during my university days, I knew only too well how many punters used to back their favourite jockeys in daily multiples, regardless of the quality of their mounts – Coral, Ladbrokes, William Hill et al tried their best to crunch Fujiyama Crest’s starting price. And they did a good job, forcing what was a 12-1 chance before the Ascot meeting began into a red-hot 2-1 favourite.
The off-course bookmakers wanted to back Fujiyama Crest into odds-on favouritism but their on-course counterparts were having none of it. They decided that they were happy to stand Fujiyama Crest at around the 2-1 mark and no-one was more aggressive in his stance than Gary Wiltshire. He had rated Fujiyama Crest as a 10-1 shot so he was not going to pass up the opportunity to lay it at much shorter odds.
It is horse racing history that Fujiyama Crest led all the way to beat Northern Fleet by a neck and his 16 other opponents by at least another two lengths. Wiltshire lost more than £800,000 as a result of Dettori’s magnificent seven and faced financial ruin. But even today the big bookmaker says that he would do the same thing again.
Betting shop punters such as Darren Yates, who won more than half a million quid, were lauded by most media organisations as the ones who had struck the good bets on that September day. They had not. They had backed a 25,000-1 winner when the true odds were more than 100,000-1, whereas Wiltshire had backed a 1-2 loser when the true odds were 1-10.
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What is the best bet that you have ever placed? And what is the bet that you regret most? Send me your comments.
