Cunliffe said it was three years earlier than he anticipated. He was working at Boston Consulting Group and he and wife Karen Price had just bought a small house in Grey Lynn with a mortgage to pay off. Price says they had returned from the USA with $5,000 between them.
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"We had spent all our money. And we had a lovely time, I don't regret it. But it was definitely time to make money now and work hard. And he was kind of short changing that side of the deal because he was off to do the politics thing, and it was a big paycut he took going into politics."
She agreed to let him stand, partly because the seat was held by National Party minister Marie Hasler and she didn't expect him to win it.
Cunliffe was known in Labour's Auckland circles from his involvement in Tizard's Auckland Central seat.
His late father's involvement with the Labour Party in Timaru helped and Cunliffe's decision to work in the business sector after returning from the USA.
Mike Williams, Labour's campaign manager in 1999, said the party was short on people with business backgrounds. "He had a good one. It's the same reason I went after David Parker - too many teachers and unionists."
Cunliffe was one of nine candidates. He had done the spadework around the electorate branches, including Don Clark who became Cunliffe's campaign manager and had the support key party figures such as Tizard and Hunt. He'd taken the precaution of meeting then Waitakere Mayor, Bob Harvey - another influential figure for Labour in the West. Harvey: "When he walked into the room in a cafe in Ponsonby I was stunned by his presence and charisma, and thought wow, wow. I knew then, instinctually, he would head the Labour Party."
David Jacobs, who also sought selection, said there was little surprise when Cunliffe won it. "He'd done all the work, building relationships among party members in the electorate and he gave an impressive speech. He wore a Labour rosette that night. It was a shrewd move, because already he's saying 'look, I look like the candidate.'"
Former President Mike Williams first impressions of David Cunliffe were not as favourable. It was at the party's 1999 campaign launch and Cunliffe turned up with bright red hair - the result of an overzealous hairdresser for a fundraiser whom Cunliffe claims was "a Tory."
David Cunliffe has his hair dyed as part of a fundraising effort. Photo / Kenny Rodger
It ensured he got a reputation for self-promotion before he even entered Parliament. The Herald awarded him "best self promoter," reporting he also handed out copies of the 'Cunliffe Courier' - featuring 22 photos of himself - at the campaign launch.
Despite Price's hopes, Cunliffe did win the seat with a solid 5800 vote majority. In the same election, Labour, led by Helen Clark, ended nine years of National Party government.
When Cunliffe first came to Parliament his colleagues were confronted with a man oozing confidence and determined to make his mark.
David Cunliffe answers the questions of protestors outside his Titirangi electorate office. Photo / Kenny Rodger
He and new MP John Tamihere were often named together as future ministerial prospects, and even leadership material. Both were on the Finance and Expenditure Select Committee, and Cunliffe was elected as chair of the commerce committee - a rare honour for a first term MP.
Cunliffe was recruited because of his business credentials and immediately put to work. Businesses were disgruntled by Labour's employment relations changes and Cunliffe was charged with rounding up chief executives to meet with Labour ministers and MPs in their dinner breaks. He also organised a business forum - but had one red-faced moment after he accidentally emailed an early draft with the expected outcomes to a staffer of then Opposition leader Jenny Shipley.
Cunliffe caught the media's attention, if not always for the right reasons. He was dubbed the 'toyboy minister" and "nakedly ambitious." Observations of his talent were usually followed by a comment about his ambition and ego. He was mocked for describing his own maiden speech as "passionate." In 2002, his supporters turned up to the Labour Party campaign launch waving placards with his name on them. In the same year, he posed for a Young Labour calendar as a Roman gladiator - a choice he now says was "a bit of fun, people had been teasing me that I looked a bit like Russell Crowe so I gave it a whirl. It's been downhill since then."
Chris Carter, John Tamihere, David Cunliffe, Laila Harre and Brian Neeson plant trees. Photo / Sav Schulman
Cunliffe describes that 1999 intake as the first political generation that had not been "scarred" by Rogernomics or the acrimony after it. But that first term also saw the start of the problem Cunliffe has struggled with since - his relations with his caucus colleagues.
Cunliffe and Tamihere gravitated towards each other, part of a group of junior MPs including Clayton Cosgrove and Damien O'Connor, and dubbed themselves the "Mods" - short for Modernisers. They met in each other's offices for drinks and discussed policies and the direction Labour might take in the longer term, post-Clark. They decided to recruit others and Tamihere says Cunliffe returned with loyal Clarkists. Whether it was innocent or deliberate, he was seen to have dobbed them in.
Cunliffe denies it: "I certainly didn't go telling tales on class mates. JT and I were in the middle of that group, not everybody agreed with everybody else and in the end it didn't go that far. But I'd reject that I dobbed anyone in."
Whatever happened, Cunliffe's friendship with most in that grouping waned after that point. One onlooker at the time recalls Cunliffe as trying to be friends with everyone. "It was like high school kind of stuff. He'd walk in [to Parliament's cafe] and go 'g'day bro' how you going?' and JT would just look at him like one of the nerdy kids had come up to him in the playground."
Tamihere says there was no big blow out and they did maintain a professional relationship. Asked about the Mods' goals now, Tamihere laughs and says "well, you always go down there with those heady ideals."
"He's an extraordinarily talented chap but you never get to see the real David. You get to see the David that he thinks you want to see. And that's his problem."
Cunliffe says his main social grouping in those years included Winnie Laban and Nanaia Mahuta, rather than the "group of blokes - Damien, Clayton, Dover, John - who would be more on the right of the party." However, some of the ideas talked about in the Mods remain with with him, in particular greater use of non-Governmental organisations and community groups to drive things.
Cunliffe says he was "a little more to the left than the right." "Someone looking from the outside thinks 'the guy wears a business suit, he does economic stuff, he must be on the right.' Actually, it's a little more complicated than that." Laban became the unofficial 'aunty'. She admired Cunliffe because of his education, intellect and Church values, but he was competitive.
"[Cunliffe] would get bolshy, and I used to say to him 'you've gotta be humble, buddy.' He's bright, he's confident, he likes to move things through, but you know with Labour Party leadership it's also having the ability and a bit of humility." Cunliffe has frequently said since then that he should have kept a lower profile in that first term while he found his feet. Of their respective political careers since then, Tamihere says he was in too much of a rush. Cunliffe was in for the long game.
"I think Cunliffe probably had, beknownst to us all, a different track. That was because he was lucky enough to obtain support from the 9th Floor more than us. So he was given greater confidence of longevity, I think."
Cunliffe and Clark
Asked how Cunliffe positioned himself in caucus in those early years, Tamihere said it was "four square under the PM's apron strings."
Dr Gregor Coster, Helen Clark, and David Cunliffe. Photo / Wayne Drought
Cunliffe does not remember the first time he met Helen Clark. Judith Tizard and Karen Price say it was when Tizard took the couple over to Mt Albert for one of Clark's fundraising debates in 1998.
Cunliffe says he had a lot of respect for Clark "And I think she thought I had a good brain and was a hard worker and safe pair of hands. I wouldn't have described my relationship with her as particularly pally in the sense others, like Chris Carter and Judith Tizard who were known as the 'luvvies.' I wasn't a luvvy in that sense."
A former minister said they had things in common: "She obviously liked him a lot so he had every right to be ambitious and think there was a track in front of him." However, that had a price. "In the Labour Party it's always best not to have obvious ambition. There's always been a sense you should pay your dues, do your job and never show too much ambition. So he was a different kind of character in that sense - there was never any doubt about what he wanted to do."
Cunliffe was appointed as a minister outside Cabinet in May 2003. In early 2005 he became minister for Communications and Information Technology and it was there he made his mark.
David Cunliffe with a broken bone in his foot makes his way to the Debating Chamber. Photo / Ross Setford
"I said to Helen don't give me the job unless you want me to have a really serious look at it - and it hadn't been an easy road for my predecessor Paul Swain."
After a lengthy review and two year stand-off with Telecom, Cabinet moved to break the company's near monopoly by forcing it to open its local network to competitors in 2006.
The Budget paper containing the unbundling decision was leaked two weeks early after a Parliamentary messenger passed it on to Telecom. The decision wiped $2.2 billion off Telecom's value in the fortnight following. He was praised by the Telecommunications Users Association for his work. Telecom's chief executive at the time, Theresa Gattung, declined to comment. Cunliffe says now he would expect her to be disappointed by the outcome. "But in my perspective it wasn't without multiple fair warnings that Telecom's behaviour was not in the public interest."
David Parker said Cunliffe handled it "very capably." "They played cat and mouse with ministers for a long, long time across both Governments, and he was the one that brought it to a head."
Karen Price and David Cunliffe at the Westpac Red Collection fashion show. Photo / Mark Barber
Like most ministers there was the occasional misjudgment. At one point, Cunliffe mused to Bloomberg that Telecom might have to cut its dividend to shareholders to fund investment. That comment was blamed for a subsequent $157 million drop in Telecom's value although the Securities Commission later cleared him of inappropriate remarks.
In another instance, Cunliffe had to delegate the decision on land to mobile termination rates to Trevor Mallard because of his earlier handling of an issue relating to Vodafone.
Publicly, his more theatrical moments also grabbed attention. There was his edict to Tony Ryall to "get back in the box, I'm running the show now" after becoming Health Minister.
He maintained Clark's trust, but alienated some other ministers. Cunliffe had worked with Michael Cullen since he was a junior MP, but Cullen declined to be interviewed for this piece. Cullen publicly backed Grant Robertson in the leadership challenge in 2013 - and quipped at the NZ Post Book Awards at the time he expected next year's entries to include Cunliffe's new book "The Dummies Guide to Walking on Water: How I learned from Jesus' Mistakes."
David Cunliffe, left, Michael Cullen and Shane Jones. Photo / Ross Setford
Other former ministers from that Labour government said while his talent was widely recognised, there was some scepticism about Cunliffe. One said Cunliffe seemed to focus more on the 'headline stuff' than the background work. One example given was over those telecommunications sector reforms in which Cullen was a key driving force but never got the credit for.
Somewhere along the line Cunliffe earned the nickname 'Silent 'T' - because of the difference inserting a 't' into the relevant part of his surname would make.
Cunliffe also had to deal with the complex, politically sensitive portfolios of immigration and health in his final years as minister. He undertook a major review of immigration settings, set up the seasonal employment scheme for Pacific Island workers. He also dealt with some tricky cases including Algerian Ahmed Zaoui, whose lawyer Deborah Manning now works in his office. It was Cunliffe who deported Rayed Mohammed Abdullah Ali, who had links to one of the pilots in the 9/11 attacks and was in New Zealand on a student visa. Another high profile case was Iranian asylum seeker Ali Panah who was then in jail on hunger strike trying to prevent deportation.
A less successful effort was his attempt to lure expat New Zealanders back home with a new website which included a list of goods - including condoms and Big Macs - that were cheaper in New Zealand than the UK.
While Cunliffe was regarded as keen to get Clark's favour, former colleagues said he did voice his own views in Cabinet meetings even where they conflicted with Clark's.
He also kept his nose clean - Cunliffe's credit card records from that time contain nothing out of the ordinary beyond a double booked hotel room and the occasional missing receipt. Unprompted, he once sent Ministerial Services $6 in cash to cover a tip he had added to the bill at a restaurant.
His former staff regarded him as even tempered and capable of taking advice. Some were very loyal, giving up their time to work on his subsequent leadership campaigns. One former advisor: "Is he perfect? No, he's got things to work on. But when you go in as a staffer, that's your job to adapt to the guy in the chair."
Image / Murray Webb
Cunliffe became Minister of Health in October 2007. Six months later, he sacked the Hawkes Bay DHB, a controversial decision locally but one he claimed was justified by the financial and political problems, and bad handling of conflicts of interest.
Then came the 2008 election. Cunliffe was about to get his first taste of Opposition.
2008 election: Helen Clark steps down
Cunliffe was at the function when Helen Clark ceded defeat and announced she would step down.
Immediately confronted by the media, he said he had no intention of running to be leader.
However, he now reveals that he did subsequently put his name forward at one stage because he was encouraged to do so. He will not say who encouraged him and said he did not push the matter because he acknowledged he did not have the experience in Opposition. "There was, I think, a fairly widely shared view that perhaps later on it might be appropriate for me to have a chance to lead the party."
Tizard says she spoke to him at the time. "My view was that it was probably too soon, but my comment was 'if you think you've got the numbers, go for it. If not, get the numbers.'"
The decision to hand over to Phil Goff was made at a meeting of Labour ministers before the Cabinet meeting. One minister at the time said Clark had proposed Cunliffe as deputy, but Goff made it clear he wanted Annette King.
Goff recalled a "vague suggestion" from Cunliffe that he might seek the leadership, but he did not formally put his name up.
2008 - 2011: The Goff years
In its first years in Opposition, Labour was struggling in the polls and Goff could not get traction as preferred Prime Minister.
Phil Goff and David Cunliffe. Photo / Mark Mitchell
If Cunliffe himself wasn't positioning himself to take over, his supporters were rattling the gates. There were damaging leaks suspected of coming from Cunliffe's supporters. There was an anonymous letter Chris Carter sent around the Press Gallery in 2010 criticising Goff and for which Carter was expelled.
Cunliffe was the finance spokesman when Goff stepped on the stage in the election campaign at the end of those three years for the Press newspaper's debate with Key. Goff held until his ground until Key asked where the money to pay for Labour's spending promises was coming from with the repeated "show me the money" refrain.
Goff foundered, failing to even bring up the capital gains tax revenue which had been released. After the debate, Goff called Parker off the campaign trail to help with the full costings. They were released in full within days, indicating they were at least almost ready.
However, some of Goff's supporters blamed Cunliffe for failing to deliver the figures earlier. Sources said throughout the year much of the policy work in Cunliffe's area, including the capital gains tax policy, had been done by associate finance spokesman David Parker and revenue spokesman Stuart Nash.
Cunliffe rejects this, saying he "worked around the clock" and was heavily involved in policy formulation. Of the debate, he said he had offered to be on the campaign team but was not included. He had also not known the debate was coming and would have been happy to help with the preparation if asked. "I certainly thought it might have been helpful for the finance spokesman to be a little more involved in case those economic kind of questions arose."
Tizard was no longer in Parliament during that time, but doesn't believe Cunliffe undermined Goff. She said if he gave an undertaking such as commitment to support a leader "it is a positively Victorian matter of honour for him to stick by his word."
"I think Phil and others quite rightly saw him as the threat, but instead of trying to make him as useful a future leader as possible, they tried to make him the enemy. I think a lot of the present problems of the Labour Party come from that misreading of both David's character and how you form a good solid caucus."
Goff says he does not blame Cunliffe for it. "I take responsibility for myself, I don't blame other people."
2011: Cunliffe versus Shearer
Goff stepped down immediately after the 2011 election and finally the time had come for Cunliffe to put his hand up. The problem he faced was that the years of ambition, eye-rolling moments and the perception he and his supporters had white-anted Goff had left a legacy.
He needed caucus support and he lacked it. The anti-Cunliffe sentiment was so obvious it even had a name. The MPs opposed to him were known as the ABCs - 'Anyone But Cunliffe.'
The ABCs settled on first termer, David Shearer, as their contender. Cunliffe put up his old friend Nanaia Mahuta as his running mate.
Although it seemed obvious to onlookers that he did not have the numbers, Cunliffe appeared to believe he could win, buoyed by the reaction of party members after the roadshow presentations the contenders had to do. Karen Price, was his helper and says it seemed an unfair contest. She also believed Shearer had an unfair advantage - the backing of Phil Goff's leader's office and resources.
One campaign helper said Cunliffe genuinely believed he could get there. "There was a lot to overcome for him, perceptions about him. He knew the odds were stacked against him, he was realistic. But he didn't go into it half-arsed."
There were reports Cunliffe was promising positions, such as finance, in return for support which Cunliffe denied.
Cunliffe says now his defeat was a "big disappointment." "The typical pattern was I set my sights on something, I worked bloody hard and usually I achieved my goal. This time I didn't, so there was certainly a lot of soul searching going on."
2011 - 2013: The Shearer years
Cunliffe stayed on the front bench under the new leadership of David Shearer but lost his treasured finance portfolio to David Parker and instead picked up economic development.
Photo / Michael Craig
Behind the scenes, the Labour Party was putting in place constitutional changes to allow the party's members and union affilates to vote for the leader as well as caucus by way of a 40/20/40 split. A more controversial provision required the leader to get 60 per cent support of caucus at a regular confidence vote. Shearer was due to face his vote a few months later and the change meant just 40 per cent of the caucus could force a challenge. Cunliffe repeatedly refused to say whether he would support Shearer in the vote in February, taken as a sign he was considering a challenge.
Shearer called a confidence vote for the next week and, whether fairly or not, Cunliffe now stood accused of undermining both Goff and Shearer.
He was punished for it by open animosity. MPs turning up for the impromptu confidence vote did not cushion their shots, including Chris Hipkins - the party's whip at the time who also worked in Cunliffe's office for a short period before the 2008 election. David Parker and Shane Jones also castigated his disloyalty.
Straight after Shearer was endorsed, he demoted Cunliffe and stripped him of all his portfolios. Cunliffe disappeared on a summer break. He emerged again, subdued, in January at Ratana with a new beard. This time he was quick to pledge loyalty to Shearer and fell silent.
Cunliffe maintains he was not challenging at that conference, something he says is a "ridiculous proposition." He had not made up his mind about the February vote and needed to consult on it first. He conceded he could have chosen his words better.
He describes the time on the backbenches as a humbling time. "I worked really hard to be very clear to everybody that I was there for the team, not for myself. I learned quite a bit by that time on the backbench."
Another senior member of Labour agrees Cunliffe "took his medicine." Price said it was hard watching Cunliffe go through that. She did not believe he had been planning a coup - not least because he hadn't discussed it with her at all.
"It's not that I wear the pants but it's a big deal becoming the leader, so you have to talk about it with your wife. I think he was set up."
Image / Guy Body
It was punishing at the time - but the changes made at that conference saw the cards fall in Cunliffe's favour. He would no longer need to win over the majority of his caucus to become leader. Cunliffe had lost the battle, but the war was still an open contest.
2013: Cunliffe Ascends
David Shearer stands down as leader of the Labour party. Photo / Mark Mitchell
When Shearer announced he was stepping down on 22 August 2013, Cunliffe was at Sealord House in Wellington talking about mussels in his new fisheries role. He got a text message to return for an urgent caucus meeting.
He says he had no idea anything was amiss. "I knew that things were getting to the point where they would possibly get unstable but it still surprised me. It came earlier."
Shearer's resignation was prompted by budding plans by Maryan Street and one other MP to prepare a motion of no confidence for caucus the next week. Somehow Shearer got wind of it and moved.
Price said Cunliffe made up his mind to stand over the weekend. "His phone was getting monstered by people saying 'you have to do this.' Then he turned off all the phones to make a decision. There was some kind of inevitability about it."
Cunliffe announced he would stand at a theatrical campaign launch four days later. Grant Robertson and Shane Jones had also put up their hands. It kicked off the new leadership contest process the party now had in place.
Price took leave from work to travel around the country with him in a role she describes as part loving wife, part nag, and part glorified PA.
"I wasn't there for the first two days, and by then he'd lost his iPad, iPhone and laptop and no one had fed him. At that point, I thought I'd better go, just to make sure he got fed."
Cunliffe's campaign was an open pitch to the union movement and activist left. He embraced socialism, and followed it up with a brace of promises, many around wage increases and working conditions. One former colleague observed it was a canny move to target the unions. "If you want to be the boss of that mob you have to look at who's got the organisational muscle 24/7 to organise for you."
On 15 September 2013, Cunliffe was announced as the new leader on the first round with just support of just one third of caucus - but a resounding 60 per cent of the membership and 71 per cent of the unions.
Mike Williams had also subsequently recovered from his first impression of Cunliffe's scarlet hair. He supported Cunliffe in the leadership bid last year. "Cunliffe can cope with the cameras. I thought Cunliffe would be good in a campaign, and he runs good campaigns in his own electorate. I've seen him in debates and he's very good. I think when it comes to going one on one with Key, he was certainly the pick of the three."
Cunliffe began his leadership by tilting to the left - toward the embrace of the unions. His first announcement was the repeal of some of National's employment relations laws and a promise to restore power to the unions.
Shane Jones, David Cunliffe and Grant Robertson. Photo / Natalie Slade
That took some by surprise. Someone who knew him in his Boston Consulting days said he was sure he wasn't the only one surprised by a Cunliffe they had not seen before at that point.
It opened him to criticism for saying different things to different audiences - as soon as the CTU speech was over he told media the promises would only happen if finances allowed.
He had a rocky start to the leadership. He was criticised for taking aim at Key's personal wealth given his own home was in an equally leafy suburb of Herne Bay. It was discovered his CV was inaccurate and outdated. He was caught out using a trust during his leadership campaign to try to keep his donors anonymous. Ironically, over-inflated claims of donations to Labour from Donghua Liu may have helped him - caucus have solidly backed him against what they believe is a Government smear campaign. More recently there was his reference to any dissidents in caucus as 'scabs' and the heartfelt 'I'm sorry I'm a man' comment to a domestic violence conference - ruining his otherwise strong message.
Asked what the biggest mistake of his leadership has been, Cunliffe says it was the use of that trust. Cunliffe has named the three donors who were willing to be named and swears he does not know who the two others are whose donations were returned. The three he named were his former Boston Consulting Group colleague Perry Keenan, Labour-friendly businessman Selwyn Pellett and Tony Gibbs. All three had also donated to Mr Cunliffe's electorate campaign in 2011. Parker agrees it was the most damaging mistake. "Because I think it hurt him. There was nothing illegal about it, but I know it's the thing he most regrets."
Cunliffe's deputy David Parker publicly backed Shearer in 2011, but refused to reveal who he supported in the 2013 run-off. "I felt whoever was leader, there was a need to build bridges. And I thought I was one of the ones who should do that."
Parker says Cunliffe tends to have a consensual style of leadership, not because he has to but "because it's his inclination." "David won the leadership race with a resounding majority, and everyone committed to making it work."
Moroney said she chose Cunliffe as leader not because of any personal friendship "it was about who could do the job effectively for us." "Placed under the most extreme pressure, I've never once seen him lose his rag. Never once."
Cunliffe says he intends to stay on if Labour is in Opposition after the election when he faces a confidence vote. His supporters agree - Tizard points to Helen Clark staying on after losing in 1996. But some former ministers say Cunliffe's situation is different. Clark had a strong core of experienced supporters behind her, ready and able to keep caucus in line. Many of Cunliffe's supporters are relatively new to Parliament or junior other than Nanaia Mahuta and Sue Moroney. Cunliffe names his 'kitchen cabinet' - the group he calls on when there is a sticky matter at hand - as David Parker, Grant Robertson and "the venerable and formidable" Annette King. None were Cunliffe supporters in the past.
But Cunliffe does have a strong power base in the wider membership, especially in Auckland. That could again prove his saving grace if there is a contest.
Back in New Lynn, his loyal electorate helper Don Clark says as far as he is concerned Cunliffe hasn't put a foot wrong. "You won't hear a word against him from anyone round here. You're in the heart of Cunliffe country now."
Prime Minister John Key and Labour leader David Cunliffe. Photo / Dean Purcell
Read more in our David Cunliffe series:
• The man who would be PM
• 10 things you didn't know about David Cunliffe
• David Cunliffe: Me and John Key
Read our John Key feature from 2008:
• John Key: The man who would be PM
• In search of John Key
You can receive special editions of the Herald Unauthorised Biographies of David Cunliffe and John Key. Register now at nzherald.co.nz/ebook for details.