He's still a senior sergeant but since his election has been seconded full time to the association, where he also chairs the board of directors, and the Police Welfare Fund.
It's a job he has been passionate about and one he is not looking forward to leaving. But, it's time.
"I said three years ago that this would be my last term," he said.
"I've been a police officer for 40 years. But I'm young enough and I want to do something else before I retire or turn my toes up.
"I'm not sure what I want to do. I'm an open book. I'm doing what I've always advised other people not to do - I'm going without something else to go to.
"I would like to think I can find something that I can be as passionate about as I have been about this. I'm hoping that there is something out there.
"I haven't seen anything yet that's spun my wheels, if you like. I'd like to think I could get out there and still make a difference."
O'Connor has a few things he wants to tick off his bucket list. Writing - he's a keen poet - and public speaking are at the top. He also wants to spend a bit more time with the family that have regularly and unavoidably taken a back seat to policing and its issues over his tenure.
It's a bit of a leap of faith. It's a hard job to walk away from. "I've seen a lot of people stay on one term too many. I promised I would leave and if you start hanging on you're compromised to an extent. I don't think it was really an option to stay on.
"And the association is in good shape, we've got some good people who can come through and carry on the good fight.
"I have to say I'm probably at the top of my game at the moment ... "It's a good time to hand over the reins to someone else.
"Whoever comes in, they can build on what I've done."
During his time as president O'Connor has been the voice of the police, the mouthpiece for his members. Whatever their issues are, he brings them to the table. Contrary to what some think, the views he gives are not his own.
Firearms and the arming of the force has been one of the ongoing battles, with a renewed focus this week after claims at a select committee hearing at Parliament that a mass shooting is "inevitable" unless the country's gun laws are tightened.
O'Connor has taken a lot of flak for the fight he has led, and he makes no apologies. However, he does want people to remember that it's only one of the issues he's front footed over his two-decade run.
"I'd hate that to be the defining point of my time here. It just happens to be the issue at the end," he said.
"In 2009 we had nine police officers shot, two of them fatally. Police did nothing. At the time I said to the commissioner 'look, we've got to do something here'.
"If that happened in any industry you'd start to get a political build-up ... A demand for something to happen. The members were saying nine of us have been shot and nothing's changing. That's when we went to Norway and found that they were in the same situation as us and they were having the same debate."
As a compromise, Norwegian police implemented a guns-in-cars strategy which O'Connor said appeased front liners who felt that their concerns had been acknowledged and addressed.
"In New Zealand nothing changed. As a result there was a build-up within our membership, a demand that police officers be armed. We had our annual conference and a remit was passed that police officers should be armed. So that is the official stance of the Police Association."
At the time 70 per cent of front line members wanted to be armed, and 60 per cent of all members felt the same. A public survey showed that half of New Zealanders were also on board with an armed police force.
"The police finally adopted what we call the Norwegian model, putting firearms in some of the cars," O'Connor said.
"That was late but the officers felt someone was listening and there was an acknowledgement that things had changed out there. That's the time a lot of firearms started to appear on the streets as well."
The introduction of firearms to police cars took the sting out of the demand, O'Connor said, but the association still felt it was a necessary evil.
"I think that will happen and it's sad, but that's when the true debate will start. There'll be a realisation that, hey, it's time. I hope that doesn't happen."
The number of firearms in the community was a huge concern for the association. O'Connor said officers were seizing guns on a daily basis. The fact they were so readily available coupled with the "preparedness" of criminals and would-be offenders to "have a go" at police was dangerous.
"Our members have been telling us for three or four years that they have been stumbling across firearms day to day that they just simply were not coming across before,' he told the Herald.
"We have been writing about this for years. The last three police ministers have all said 'what problem? There is no problem.' Then Kawerau happened, four officers shot on the job and all of a sudden the minister says 'oh, we better have an inquiry'."
In March Police Minister Judith Collins announced an inquiry into the availability of firearms in New Zealand as a direct result of four police officers getting shot during a cannabis operation in Kawerau.
"I think as long as something meaningful comes out of this arms review, it might stem the flow of firearms [into] illegal hands, then maybe we can stay unarmed," O'Connor said. "But it'll be that major incident that will make it happen. To me it's one of those issues where the politics have taken over the policy."
O'Connor believes the New Zealand police are a great force, and one the public should be proud of. But like any government agency, there's always a way to improve.
For him the simplest way to bolster the force is, to bolster the force.
"One of the best things happened in Counties Manukau. It was almost a bit of a basket case. I used to visit there and everyone was down in the mouth, there were homicides every weekend, nobody really believed they were making a difference there.
"Then in 2008 the district got an injection of 300 staff and District Commander Mike Bush [now the Police Commissioner] used them smartly. He didn't just tack them on to existing structures, they set up a whole new structure - and it worked.
"The rest of the country has been expected to do exactly the same thing, without the extra staff. I think if you proportionately gave that level of staff to districts around the country, the public would get a very, very good service. They don't get as good a service as they got."
When O'Connor started out as a fresh-faced constable, aged 19, in Wellington, the job was very different. There was no need for tasers or pepper spray. There was no such thing as methamphetamine. Officers didn't go into confrontations expecting an offender to whip out a sawn-off shotgun or machete.
But the biggest difference was respect. Police had a lot more of it than they do today, he said.
"Even in the early years ... police officers still did get hidings and there were assaults but there was still a basic understanding that the uniform did provide protection. Even the criminals knew there was a line you didn't cross. That line's gone now.
"There's basically a generation that's growing up, I believe, without consequences."
O'Connor said fleeing drivers was the kick-starter to that. He said there was a "whole generation" prepared to take the cops on.
"They will have a go if the police try to pull them over. If they have a go, they know police will have to pull out.
"They've grown up well aware that police have very limited powers, so it doesn't take long before that translates through to everything else they do - like assaults."
That attitude led to police having to be more brutal. OC spray, tasers, stab-proof vests were introduced.
O'Connor said the way police behaved was reflective of their society.
"If you've got a more brutal society, you've got a more brutal police," he said.
