Key appeared fresh and new, and above all, keen. He wanted the job of Prime Minister, and his childlike zeal on election night was endearing.
Within a year I was uncomfortable. Within two, it felt like I was sitting on a bed of nails.
I'm not sure of the exact moment I knew the Key train had uncoupled from its charisma caboose. All I know is the train thundered on without me onboard.
Logically, it was likely when I realised that Key had no understanding of, or respect for, the environment. He seemed to me to care only for running New Zealand like a huge corporation by squeezing every last dollar out of it - no matter the downstream consequences.
I say "downstream" because my focus back then was firmly on water quality. The Key-led Government has played a massive role in the funding of dairy and irrigation intensification since, leading in turn to the steady decline in the quality of our nation's waterways.
I'm not so naive to think he was solely responsible for such cynical fare. However, as the frontperson for the tragedy of losing our swimmable rivers, one must understand that some of us will never forgive such recklessness.
A good money man? Key's bold and brassy belief that he managed the Global Financial Crisis well is, shall we say, deluded. He got lucky. Pure and simple.
I'll wager that within the next 12 months, and well before the 2017 election, our economy will match the global outlook perfectly. It'll be munted. He is less an economic guru and more a tinny bastard, frankly.
I say this in complete awe at Key's uncanny ability to ride the rollercoaster of pure providence. Despite the poor getting poorer, and the rich getting richer, he somehow managed to convince the wider electorate that he was a financial whizz - as opposed to the money trading gambler he ultimately is.
Inequality has never been worse in this country, and that has to be the test. Key's reign encouraged many to hate on the poor. Little did he and his cohorts comprehend, it also taught just as many to hate on the rich.
This will not be solved by a new face at the top, or by an obsequious media happy to create corny commentary for those of you who actually care that he is exiting stage right.
My biggest thumbs down is reserved for the free licence he issued to a particular segment of male culture.
It's never a good thing when the public learn about the pubic. Key's predilection for appearing on trashy radio means we all possess the knowledge - like it or not - that he doesn't trim his "downstairs", has urinated in the shower, and had a vasectomy.
Call me passé but the title of Prime Minister should mean something. Jumping in a cage and picking up a bar of soap - in a nod to prison rape - is probably not a component of that.
Ponytail-gate sealed it. The man sent a message to the world - and I mean the world - that he was an unsophisticated fool at best, and a creep at worst.
Since then the planet's got Trump, so maybe Key won't be remembered for those weirdnesses. However, his legacy is that he contributed massively to the type of male culture in New Zealand that sees women as not much more than just pom-pom girls cheering from the sidelines. On a good day.
So, those are my top three gripes, and you'll have yours. Is there any redeeming feature about Key that I could mention? Yes, I think there is. Work ethic. He had a good one.
It's the end of an era that I'm glad to wave goodbye to. It was eight years of teeth gritting, face palming, guttural groaning, a fair bit of drinking, and throwing things at the TV. If you think he's aged, you should see me.
So long John, and thanks for all the (dead) fish.