O'Brien joined that club as a trainer a long time ago, however, and says he always fancied Serpentine's chances of upsetting the odds as he now eyes up a raid on the St Leger or the Arc.
The victory meant he surpassed Robert Robson, John Porter and Fred Darling as the Classic's leading trainer and after Love also conquered all in the Oaks, even the scrupulous master of Ballydoyle raised a grin.
O'Brien said: "We try to give each horse the best chance of winning and ride them all accordingly".
"They are so hard to make them happen". There are so many people involved all the way up to the present time, and it's incredible, unbelievable, really.
"You do your best and when it happens you accept the result".
"It's unbelievable really. He has some pedigree and we always thought he would stay well", O'Brien said.
Stunningly, McNamara had not ridden a victor anywhere since last October.
"Surreal empty stands and I did not hear a sound from behind me all race", said the 30-year-old McNamara.
"I think I am about to wake up from doing a piece of work on the gallops!" He reported his instructions from O'Brien as being: "Jump off and go your own tempo". McNamara told the Racing Post.
"I had been saving myself", he joked about his win drought. Having been narrowly denied victory in last week's Irish Derby aboard Tiger Moth, McNamara will be riding O'Brien-trained outsider Fort Myers in the French Derby at Chantilly on Sunday, after which he will return to Ireland and spend 14 days in quarantine due to the current travel restrictions in place to combat coronavirus.
"I'm not the lightest in the world, but Aidan knows I'm as fit as a fiddle and I'm extremely grateful to him and the owners for the faith they've shown in me".
"I am not sure I would be able to do so at the family home as my father has probably roared the house down!" Serpentine built a comfortable lead early on in the field of 16 3-year-olds, as Khalifa Sat, Amhran Na Bhfiann and Max Vega chased.
Khalifa Sat's jockey Tom Marquand could have been forgiven for giving a cheeky wink at second favourite English King's trainer Ed Walker.
Kameko, victor of the 2000 Guineas, was a fast-finisher in fourth, having been sent off the 5-2 favourite, while English King was fifth and Mogul sixth under Ryan Moore.
O'Brien's first choice jockey Ryan Moore finished sixth on his selection Mogul.
This year, however, he heads there with Kameko, victor of the 2000 Guineas in June and one of the favourites at 9/2 in the latest horse racing betting for the Derby.
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