Not to be a pseudo-intellectual, but this confuses partial orderings and total orderings. It makes for a fun discussion, but I hope Paul would agree that there's obviously no "best essay", real or hypothetical.
You always have to try or you wouldn't have a chance. But you can't just sit down and determinedly write your best material ever, with any kind of certainty, right when you decide to.
Good fortune is going to need to smile.
His writing is consistently flat, uninspired, and egotistical. He's ok at writing clear prose and this plus his success in relation to YC has made him popular among technical people that also embrace capitalism. Anyone outside of this little cult realizes that pg says very little of value, particularly when he decides to comment on subjects outside of his capitalistic and technical wheelhouses. I have not read a single pg essay that touches on culture, ethics, or general epistemology that has given me anything other than a complete groan of a reaction and astonishment that this is the sort of thinking that passes the "high-quality" bar for the average technologist.
pg can try as hard as he can to write the "best essay". He will never convince this reader since he occupies a completely different world and basically isn't even capable of speaking to this audience in the first place.
...just to lengthen this comment more than is due, the quote is astonishing. I mean, how arrogant do you have to be to claim that the past hundreds of years of literary development, in which the notion of "best essay" is considered at best completely relative and at worst nonsense, must be wrong and that anyone who thinks otherwise must just be a "pseudo intellectual" (read: someone who disagrees with paul graham). He's really high on his own supply.