The truth behind the mysteriously unconfirmed $23k payment is even funnier than that. The reason the $23k payment never confirmed is that it spent a change output from his wallet that had fallen victim of transaction malleability.
So not only would “bigger blocks now” not have solved the problem, but segregated witness *would* have prevented it happening. So the transaction he tried to use as an argument for bigger blocks was actually an argument for segwit. :)