Vincent O'Brien: the astonishing coup that founded a racing empire

Recalling some of the greatest gambles in racing history. This week: Vincent O'Brien and a memorable coup

Vincent O'Brien, one of the most revered names in horseracing, made his first imprint on the sport aged just 27 when he pulled off an astonishing coup by landing the Irish autumn double in 1944. It is a success that echoes down the decades.

The 400-1 ante-post double won by Drybob in the Irish Cambridgeshire and Good Days in the Irish Cesarewitch laid the foundation of O'Brien's fortune. From there he became one of the best trainers of all time, first over jumps and then on the Flat, and established Ballydoyle as the pre-eminent training centre in Ireland, leading to its successful partnership with Coolmore that continues to this day under his namesake Aidan O'Brien.

Gambling for a living

In 1944 O'Brien was in his first year as a public trainer, having worked for a year as a teenager for professional trainer Fred Clarke and then spent a decade learning how to lay a horse out for a specific target while assistant to his father, Dan, at the family home, Clashganiff House in Churchtown, County Cork.

The young assistant worked unpaid and "soon realised that the only way he could make a living was to prepare horses for gambles and to land them successfully", according to his official biography written by Ivor Herbert.

In that time the stable won several big handicaps including the Irish Cambridgeshire and Irish Cesarewitch – in different years – with O'Brien jnr supervising much of the training as practice for the great coup of 1944.

A pair of astute acquisitions

On his father's death in May 1943, young Vincent took over a string of ten horses and in December that year went to the sales in Newmarket to build up his team. He bought Drybob for 130gns and persuaded a new acquaintance, owner-breeder Sidney McGregor, to send him Good Days to race in neutral Ireland rather than in wartime-restricted Britain.

Good Days became O'Brien's first winner as a public trainer when landing a gamble in a bumper at Limerick Junction (now Tipperary) in May 1944, and Drybob won at the same course in August, with both horses then entered for the Irish Cambridgeshire and Cesarewitch.

The money goes down

There was a strong betting market for what was known as the Irish autumn double. Frank Vickerman, an English wool-broker based in Dublin, had become O'Brien's first owner and urged him to gamble on both races.

The trainer told his biographer: "Luckily for me, Frank Vickerman had asked me, 'How about a bit ante-post on the double?' I very modestly said, 'Have me £2 each-way.' Frank had £10 each-way and stood to win £5,000, and I stood to win £2,000."

Vincent O'Brien with Lester Piggott (right), who rode many of his great Flat horsesCredit: Caroline Norris (racingpost.com/photos)

The two winners both started at 20-1 but the bets were struck at longer ante-post odds with bookmakers in both Ireland and England. According to the trainer: "In England bookmakers were prepared to take quite a bit of money on Irish racing. English racing was so limited at the time that they could make a market."

Dramatic finishes

Drybob was the stable's first string for the Cambridgeshire and managed to keep the gamble alive, but only just. Bloodstock Breeders' Review reported: "Dawros looked very much like winning, but the irresistible [Morny] Wing challenged strongly and in seeming miraculous fashion got his mount Drybob up to make a thrilling dead-heat."

Good Days, a 100-1 shot over a trip far short of his best, was among the also-rans.

Four weeks later the two stablemates lined up again over double the distance in the Cesarewitch at Phoenix Park under joint topweight of 9st, and this time the stayer Good Days was the first string. He prevailed by a neck in a desperate finish, with Drybob fourth.

The combined prize-money for the two handicaps was £584 and O'Brien's bets brought him a personal profit of about £1,000 – a big sum in 1944.

A lasting legacy

Vickerman won a considerably larger amount and O'Brien benefited, with the owner using part of his winnings to buy Cottage Rake. That paved the way for O'Brien's Cheltenham Gold Cup hat-trick with that great champion in 1948-50.

More success flowed from O'Brien's gambling success. Many of his early bets were placed by commission agent Nat McNabb, who performed the same service for Harry Keogh and persuaded that owner to transfer Hatton's Grace to O'Brien in 1948. In the following three years, O'Brien made him the first triple winner of the Champion Hurdle.

After moving from Churchtown to Ballydoyle, O'Brien became the only trainer ever to score a hat-trick in the Grand National (1953-55) and he achieved it with three different horses – Early Mist, Royal Tan and Quare Times. His bets on Royal Tan netted him about £4,000, and that was just after he had won with six of his seven bets at the Cheltenham Festival.

O'Brien relied less on gambling as he moved into Flat racing and built up Ballydoyle into a great force, numbering six Derby wins and three Prix de l'Arc de Triomphes among his many successes, but everything traced back to his 1944 coup.

Speaking many years later of the fortune he made from betting, O'Brien said: "It was entirely confined to the horses I trained myself. I learned the lesson, luckily for me pretty early in life, that betting on other people's horses wasn't exactly a paying game."

Read these next:

JP McManus: 'We loaded up on him – he had been laid out for the race'

Noel Furlong: 'I had £300,000 on Destriero and a lot on the double'

Yellow Sam: a perfectly executed gamble that netted Barney Curley a fortune

Albert Davison: a master plotter who ensured Irish betting shops took a bashing

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