"Naturally it would be an enormous thrill to train a Derby winner too and I hope it happens, but I may never train one," O'Sullivan said.
"It's up to the horse at the end of the day and we're really pleased with him.
"I've found it was a lot easier riding them than it is training them.
"I'm lucky to win the Derby twice as a jockey and personally I got the biggest thrill from Popsy winning. She was the only filly in it that year and she came from last on the corner. It was a huge run.
"She had run an average third leading up to it and the owner wasn't keen on running so we had to persuade him. We decided to put a hood on her and have a crack and it worked out well.
"It was a bit different with Surfers Paradise. He had better form going into it and was expected to win."
That same expectation is on Dragon Leap, so how does O'Sullivan feel about his prospects of possibly achieving the slice of New Zealand Derby history with him?
"He had a soft run when he won last time and he has really bounced through it and should run well," he said.
"We'll just have to see if he is good enough to run the distance out. Genetics suggest he will, but you never know until you try them."- NZ Racing Desk