Equally, he may be about to ride off into the sunset, remembered as COVID minister, for inheriting the prime ministership from Jacinda Ardern and losing two elections to another Chris.
It's feast or famine for Labour, Mr Hipkins and the left as the November 7 election reaches its endgame.
A polling average shows very little between the left bloc and the three-party coalition, which Mr Hipkins said he was finding hard to parse.
"We're feeling very, very good," he told AAP this week.
"One of the weirdest things about this campaign is reconciling opinion polls with what we're actually experiencing.
"This is my seventh election as a candidate and probably one of the best moods that I've ever seen on the ground towards Labour."
Whether that's wishful thinking or well-grounded confidence will be borne out in coming days.
What is clear is that the affable Wellingtonian - who very few predicted would be prime minister, and yet could be twice - should have never made it this far.
In January 2023, Mr Hipkins succeeded Ms Ardern, with a top preferred prime minister result over his career of 0.3 per cent.
After multiple ministerial sackings or exits during his nine months in the top job, which ended with a trainwreck election loss, most believed his time as leader would be short-lived and Labour had no chance of winning in 2026.
Labour has never won back government after just one opposition term in its history.
Few defeated prime ministers anywhere re-claim the office after an election loss - and none in New Zealand since 1960.
As he contends the 2026 campaign, Mr Hipkins has offered "honest reflections" of things he got wrong last time in government, including on youth crime and lockdowns.
"I've never believed politicians who believe they are infallible ... humility is a massively underrated quality in politics," he said.
"I had nine months as prime minister and I learned a hell of a lot from it, and that will make me much, much better prepared going in next time."
In opposition, Mr Hipkins has operated a small target strategy, releasing few policies until the final months, a highly-criticised approach that kept a focus on unpopular Prime Minister Chris Luxon and his sometimes dysfunctional coalition.
He rejects the idea that Labour's final policy suite is modest, another charge he's heard often.
"There's some bloody bold policy ... free universal primary healthcare is a transformative policy," Mr Hipkins said.
"A capital gains tax will be the biggest change to our tax system in 40 years since a GST ... I don't think what we are promising lacks ambition."
On Monday, Labour received a welcome boost, labelled in an Ipsos poll the party of choice to handle nine of Kiwis' top 10 issues, including the main challenge of the cost of living.
Still, a triumph is as conceivable as a loss.
On most polls, the left bloc is marginally behind the right bloc and likely to be reliant on a new teal party, Opportunity, making it into parliament and picking them to break the deadlock.
Opportunity's polling average is six per cent, just north of the five per cent threshold it needs to clear to have any MPs.
Opportunity leader Qiulae Wong has pledged to negotiate first with the party with the most seats.
That will be a close-run thing between Labour and National, but Mr Hipkins was bright and clear when asked if Labour had more likelihood of striking a deal, given policy alignment.
"That would be my assessment, yes," he said.
Those negotiations, with possibly the Greens, Maori Party and Opportunity, may be as arduous as the campaign.
Again, Mr Hipkins is optimistic, saying "the goodwill is there" to form a government before Christmas.
"We need to let the voters say before we start measuring the curtains ... I hope we'll be able to have constructive conversations," he said.
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