Six years ago, the dream became a reality, but for just a tragically short time when the little grey former European stayer Bauer carried OTI's colours across the finish, only to be shown to have been beaten by less than the length of your finger.
"For seven seconds I thought I'd won a Melbourne Cup and it felt sublime - I want to feel that for a much longer time."
To think you've won a Melbourne Cup then discover you haven't is about as cruel as the racing game can get, but O'Donnell is too much of a sportsman to dwell on that.
That will be completely erased when the win finally comes. Before OTI Racing was formed partner Terry Henderson won the Melbourne Cup with Doriemus.
Mixing with the connections of the 11 Northern Hemisphere Cup runners for this afternoon's big race at Sunday's press conference at the Werribee quarantine station you get a feel for the desperation most have to put a Melbourne Cup on their CV.
And we're talking some of the world's great trainers. England-based American John Gosden, leading the might of Coolmore and Aidan O'Brien in the English trainer's premiership, had runners at the Breeders Cup giant meeting at Santa Anita on Sunday.
At Werribee he said: "I've been asked why I was coming to Melbourne instead of going to the Breeders Cup. I said: 'I'm going to where the future of racing is, not the past'.
"You can imagine how well that went over with some of my American mates." Indeed, but then they probably have not been to a Melbourne Cup.
Wealthy Japanese owner Riichi Kondo, who has the $4.60 favourite Admire Rakti in the Cup, has become completely caught up in the hype in Melbourne since the horse won the A$3 million Caulfield Cup.
"Since I've arrived in Australia, I have just loved the country and the people so much so that I have lost a little interest in Japanese racing back at home."
Kondo said one of his 100 racehorses won a race in Tokyo at the weekend and his focus is so firmly in Australia he hadn't been aware of it until yesterday.
England's Ed Dunlop, who today produces veteran Red Cadeaux into his fourth Melbourne Cup, is desperate to win the race, especially after two seconds with the horse.
Dunlop is widely regarded as one of the world's finest exponents of travelling horses internationally and has won major races on practically every continent.
Asked what it would mean to finally win this race he said: "Everything. Beyond anything I've done so far."
Admire Rakti is a deserved favourite. His Caulfield Cup win was stunning on a tight course that did not suit his racing style and he is expected to love the wide open spaces of Flemington this afternoon.
His weight at 58.5kg looks prohibitive to some, but he is a remarkably strong stayer and the weight would be less likely to beat him than bad luck.
Riichi Kondo wants this race so badly he has instructed his team they must not bet on the horse for fear of using up too much luck.
Simon O'Donnell says although he and Terry Henderson are great mates: "Some little part of me dislikes him for having already won a Cup."
O'Donnell sums it up best: "The desire to win a Melbourne Cup can be cured only by death."
