He has taken a lot of stick, especially from his own colleagues. It has never dented him. He was knocked back and he was knocked down but he was never knocked out.
And through it all he learned. And he worked. And he waited. He always gave off the distinct air that he knew that the prize would one day be his. That confident air also didn't endear him to his colleagues.
I was never sure when he stood up whether he was going to knock one out of the park or crash and burn. In his early years, he often did both.
I was thrilled when he told a raucous Parliament that he was "running this show". Every other Health Minister ducks and weaves. They are at pains to explain in excruciating detail how the health system is not theirs to run. They say their job is simply to set high-level policy and that the many problems in the health sector are not their responsibility.
Not Cunliffe. He declared the entire health system under his care.
I liked that. It was impressive. And risky. He was new to the job. There's always a lot going wrong in health and it's not wise to claim full responsibility. But Cunliffe doesn't shirk centre stage.
Cunliffe can clearly see his worth even if he struggles to get his colleagues to see it too.
Cunliffe was the only minister in the Clark government who had his own caucus leaking to me. None of it was earth-shattering and I can't remember ever using any of it. I always had better stuff on the failings of other ministers. There were plenty in his own team who wanted him to trip and fumble.
And so finally Cunliffe has made it. And he is off to a roaring start. He knows what he wants and he is backing his judgment.
He didn't play safe and have Grant Robertson as deputy. He also dumped a couple of his most strident caucus detractors. He left others.
He is showing the party and the country that he's in charge.
For his chief of staff, Cunliffe went outside the Wellington inner circle and beyond the party. That's a good move. He's not playing safe for the week ahead. He is preparing ahead for the election and for government. The difference from his predecessor could not be more stark.
It is clear that Cunliffe is "running this show".
Some colleagues will be left disgruntled and, no doubt, some will be waiting and plotting. It doesn't matter. The only thing that matters is winning and wielding power. Cunliffe has won the Labour leadership and is wielding the power. His goal now must be to win government. That's the result that will silence the bitter and the disgruntled.
Will he make it? I don't know. I think my original assessment stands: he will either knock it out of the park or crash and burn.
And he will likely spend time doing both. The Labour Party and New Zealand politics are in for a helluva ride.