Yes, I was thinking of this Munk debate in the other thread, where the OP had mentioned that she was surprised to discover that Douglas Murray was not a moron as she had been led to believe. Gladwell did so poorly a lot of people who were fans of his were surprised, and he later wrote an article saying that he had not realised when he went into the debate that Douglas had been a member of the Oxford Union and therefor was an expert debater.
I think he's just been so used to everyone being so enamoured of his books (which are frankly full of questionable material,) and in progressive Canadian circles he counts as an oppressed minority despite his class advantages, that he assumes he will easily beat out a guy like DM.