“You never see a bookie cycling a bike!” Well, you´re about to learn that the house doesn´t always win.
Yellow Sam – Bellewstown, Ireland, 1975
A gamble engrained in Irish racing, which is still spoken about (and celebrated) today. Barney Curley was the mastermind behind the punt which cost bookies £306,000 at the time, over £2 million in today´s money.
Curley was training to be a Jesuit priest when he contracted TB, forcing him to change course into the world of gambling, a decision that bookmakers around the UK and Ireland would be left to rue.
After a string of losing bets, Curley searched for a ´hail mary´ to get him out of jail, so he turned to the Curragh trainer, Liam Brennan. Curley had some horses in training with Brennan, one being Yellow Sam, a rather modest gelding who had failed to finish closer than eighth in nine runs over two seasons. However, Brennan was adamant that the horse had improved and his previous form, or lack thereof, was the perfect disguise for what would result in one of the most famous coups of all time.
In what can only be described as meticulous planning with military precision, Curley mapped out his route back to the black. He selected an amateur riders´ race at Bellewstown to ensure the competition wouldn´t be strong, and the likely quick ground was a big advantage.
Trainer, horse and race selected, yet it was the execution of bet placement that shows us how much of a genius Barney Curley was. He arranged for small bets to be placed in over 300 betting shops across Ireland, right before the race was to start. The bets were intentionally small enough to not raise any alarms, and the timing meant that the off-course bookmakers had little time to react.
Not only that, in Bellewstown in those days, the off-course money was usually communicated to the on-course bookmakers via a solitary phone box on the track. On this occasion, Curley hired a man called Benny O´Hanlon to occupy the phone box for 25 minutes before the race. His instructions were to appear distressed and not to budge until the race was off. Alas, the off-course money was never communicated and Yellow Sam duly held up his part of the bargain, winning comfortably.
In total, Curley managed to get £15,300 on the horse at a starting price of 20/1, netting him £306,000. He had taken on the system and won. The audaciousness of the coup will live long in the memory of horse racing fans around the world, and while many have attempted similar plots since, none have come close to Yellow Sam.
The Hole-in-One Gang, 1991
Many punters fantasise about bankrupting the bookies, but for Paul Simmons and John Carter, that dream became a reality. The two men from Essex, UK, were amateur golfers but had a keen interest in mathematics, particularly probability. This is in the days before the concept of EV (expected value) and statistical models or algorithms for winning on betting. Online betting also wasn´t a thing, and the UK bookmaker landscape included a plethora of independent bookmakers, mixing it on the high street with the likes of Ladbrokes and Coral.
Simmons and Carter were in search of a +EV angle that would allow them to win big, so they researched the true probability of a hole in one occurring in a number of major golf tournaments. Their research unearthed that there was at least a 50% chance of a hole-in-one at several of the courses. In bookmaking terms, the true odds per tournament was around even money (1/1, 2.0 as a decimal), yet they were offered as big as 100/1 by some smaller, independent bookmakers who clearly weren´t as shrewd as Simmons and Carter.
The men proceeded to place a number of doubles, trebles and an accumulator on five tournaments, where the true odds of the bet was around 32/1 – yet the much inflated odds quoted by the bookies meant they had secured a huge amount of EV, and now just needed variance to be on their side.
While most of the bets were individual singles for relatively small sums, to make the opportunity pay, the men needed to land the majority, if not all of the bets. Luckily, for them at least, there was an ace in all five tournaments, and the men had won a cool £500k- However, the fly in the ointment was that they didn´t receive all of their winnings, with some bookmakers declaring bankruptcy or refusing to pay at the quoted odds.
A true coup for the ages!
Charles Byrnes, Roscommon, Ireland, 2015
A gamble which was “good for Irish racing” according to the mastermind behind the punt, Charles Byrnes. Training out of Ballingarry County Limerick in the southwest of Ireland, Byrnes is a notorious and widely-feared figure in racing. It´s well-known that when money comes for a Byrnes runner, you take cover as a bookmaker and jump on the bandwagon as a punter. The Limerick outfit were out of luck at the 2016 Galway Festival, appearing unlucky on at least a couple of occasions, but Byrnes had an ace, or three aces as it were, up his sleeve for a lowly Roscommon meeting the following Tuesday.
Byrnes saddled War Anthem, Top Of The Town and Mr Smith in three races on the card, with the trio being largely unfancied, with odds of circa 3,500/1 on the treble. Legendary jockey, Davy Russell, who was booked to ride the trio, was the only positive angle if you analysed the form and took it at face value. However, at circa midday, a wave of money came for the three runners, with doubles and trebles the preferred bet of choice.
The industry stood to lose an untold amount of money if all three ran, but as the start time approached for the first of the runners, there was a slight unease in confidence as War Anthem hovered around 6/1 in the betting ring. However, as the tape went up, that 6/1 immediately looked too big as War Anthem cruised through the race and won very comfortably. Alas, the gamble was on.
Just 30 minutes later, Mr Smith lined up in an 80-95 handicap hurdle, and if the earlier sequence of bets wasn´t enough, he was backed from 11/4 into 7/4 on the show. Again, in a case of deja vu, Russell cruised to the lead before the last and sauntered to victory.
If it wasn´t squeaky-bum-time for bookmakers before the race, it certainly was now. An anxious hour lay ahead before the final runner, Top Of The Town, went to post in another low-grade handicap hurdle. Owned by the Top Of The Town syndicate, named after a pub in County Limerick, their namesake bolted in and the gamble was well and truly landed.
The industry is estimated to have lost in the region of £1 million, with Byrnes famously saying “After Galway, I needed that. I did my brains with Sea Light and Crystal Pearl.”
Although one would suggest, this was a plan long in the making.
D Four Dave, Kilbeggan, Ireland, 2010
Assembling a competent team is paramount to any managing director´s agenda in business, and that statement is no less true when it comes to executing a gamble. Douglas Taylor, managing director of MCR Group, a recruitment firm based in Dublin, Ireland, had plenty of experience on that front from a professional perspective, but it would be an achilles heel of sorts when he attempted to land a touch on his horse, D Four Dave.
Taylor convened 200 foreign nationals, many of whom couldn´t speak English, and gave each of them an envelope with €200, a betting slip and a piece of paper inside, as well as a stop watch. The absence of fluent English was intentional, as Taylor wanted to ensure word about the gamble wouldn´t spread and ruin the price.
The alarm was set to 18:55, five minutes before the scheduled start time of the race. Taylor instructed his battalion to approach the counter of their specified betting shop and to hand the envelope to the cashier as soon as the alarm went off, muttering the words “I will take the price!”. D Four Dave’s odds were slashed immediately, shortening from a general 14/1 to a starting price of 5/1.
While D Four Dave won the race well, and Taylor landed roughly €200,000 after expenses, one is left thinking what might have been. Many of the team failed to get their bet on and, in hindsight, perhaps entrusting non-native speakers with zero experience in bet placement might have been a sub-optimal approach. Nevertheless, I´m sure Mr Taylor wasn´t complaining.

