The aviation bigwig had known success in these parts in years past, but not recently, and he looked set for another blank this week as the last of the four days dawned and he still awaited his maiden victory of the 2014 event.
A switch in the placing of a big screen had forced the millionaire businessman to move from his favourite spot in the parade ring on Tuesday, but his luck finally changed when Tiger Roll, Very Wood, Don Poli, and Savello all came home first past the post.
The combined odds for all four amounted to a tasty 82,653/1.
“I’ll never forget this day,” said O’Leary. “It’s been incredible. You wait two years for a winner at the festival and then four come along in one day. We’ve got a couple of guests in our box and a couple of them have done a £2 accumulator on our horses.
“They’ve won over £150,000 [€180,000].”
After two poor days for the Irish, yesterday was a bonanza.
The week’s biggie, the Gold Cup, was also claimed for Ireland for the first time since Gigginstown’s War of Attrition obliged in 2006, with Lord Windermere and jockey Davy Russell scooping the trophy after a dramatic finish.
The result was only confirmed after a stewards’ enquiry to investigate the possibility of interference with the Willie Mullins-trained On His Own was dismissed and the result was greeted with predictable delirium by owner Dr Ronan Lambe and others.
For trainer Jim Culloty, it meant he could join a rare band of men who have both trained and ridden a Gold Cup winner. The Mallow-based Kerryman partnered the legendary Best Mate to success three times in the early noughties.
Culloty had endured a dreadful season, going without a winner from August until Thursday when amateur Robbie McNamara brought Spring Heeled home in the Fulke Walwyn Kim Muir Challenge Cup.
For Russell it was a day of days. The man from Youghal bookended his afternoon with two more wins on board Tiger Roll and Savello. Both were in the distinctive colours of the same Gigginstown stud which had only released him as their retained jockey in January.
There was less joy for other Irish jockeys, with Ruby Walsh suffering serious arm and shoulder injuries in a fall and Wexford’s Daryl Jacob joining him in hospital with multiple injuries after a bizarre accident when his horse was spooked by the crowd.