Colin Craig's brief and bizarre delve into politics may be over but his name remains synonymous with the defamation proceedings and dirty politics which followed the 2014 general election. Sam Hurley details the rise and fall of the former Conservative Party leader.

"This defamation proceeding has its origins in the political rise and fall of Mr Colin Craig.

"An Auckland accountant and businessman, who founded and led the Conservative Party of New Zealand between 2011 and June 2015."

This apt opening remark by Justice Kit Toogood explains how Craig, for a brief time, became New Zealand's biggest political headline and how his private life, particularly with his press secretary Rachel MacGregor, was explicitly laid bare for all to see.

Today, after more than a year of consideration, the High Court publicly released a 250-page judgment ruling on yet another Craig defamation foray.

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It involved Whale Oil blogger Cameron Slater.

It said Slater defamed Craig.

But it also said Craig sexually harassed MacGregor - a fact still disputed by the multi-millionaire property manager.

Craig was a relative unknown when he contested the Auckland mayoral election in 2010.

He finished third behind Len Brown and John Banks, a result Craig remains proud of today.

The following year the now 50-year-old founded the Conservative Party.

"He was a middle-aged man trying to have a go at politics," MacGregor later said.

Craig and his wife Helen decided to enter politics after the controversial anti-smacking bill become law, believing New Zealand's conservative citizens were being ignored.

Colin Craig, pictured the morning after the 2014 election, was polling well before the scandal dropped his popularity among voters. Photo / Michael Craig
Colin Craig, pictured the morning after the 2014 election, was polling well before the scandal dropped his popularity among voters. Photo / Michael Craig

The fiscally and socially traditional Conservatives performed relatively well in 2011 in its first national election, gaining 2.65 per cent of the party vote - more than the Māori Party and Act Party combined.

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Despite not holding a seat in Parliament, many predicted the Conservatives could play an important role in the government's make-up three years later.

But when making his way along the 2014 campaign trail, Craig's political world began to unravel.

It culminated in the spectacular resignation of MacGregor and media circus just two days before election day.

When first approached to be Craig's press secretary, MacGregor recalled thinking her boss-to-be as a "badly dressed jovial chap".

"He had his pants pulled up high, he was sort of dorky. He was a middle-aged man trying to have a go at politics," she told the court during Craig's trial with Slater.

MacGregor was initially hired in a part-time role, but later became a full-time staffer as she attempted to provide Craig with an "image that was worthy of public discussion".

The pair quickly developed a close working relationship and on election night 2011 they kissed and Craig touched MacGregor's breasts

Justice Toogood would rule "there was intimacy" between Craig and MacGregor and until after the election night kiss Craig had not sexually harassed his staffer.

"I am not satisfied that Craig's behaviour was unwanted by Ms MacGregor at that time," the judge said.

However, he added, what came next saw Craig "guilty of moderately serious sexual harassment".

One of Colin Craig's poems was titled Two of Me. Photo / Brett Phibbs
One of Colin Craig's poems was titled Two of Me. Photo / Brett Phibbs

During her time as a journalist at TVNZ, MacGregor said she had experienced "inappropriate males". However, it was Craig's mention that the cut of her top was too low, followed by a letter, which really made her feel uneasy.

She outlaid her concerns and the pair talked of setting professional boundaries.

"As we know with Colin Craig he likes to do things in a weird way, a kind of quirky way," she said.

MacGregor thought the pair had a "good working relationship" after the boundaries were established, before Craig "had gone and broken them".

"Then came the dodgy poems, and I thought 'oh for goodness sake, here we go again'."

During the Craig and Slater trial, she told the court she was curious to see what Craig had written but soon "was really offended" by the "really bad poems".

"It was awful actually, especially because he was going into detail about me physically, it was really disgusting."

One of Craig's poems was called "YAWAB", which means "you are wonderful and beautiful".

"Wonderful
"You are wonderful because you make me smile
"You are wonderful because you think like me
"You are wonderful because you don't think like me
"You are wonderful because you know how to care
"Please know that you are wonderful
"Beautiful
"Your eyes are lovely
"You look unbelievable in your new dress
"Your lips are so amazing to kiss
"Your skin is so soft
"You have the most perfect ..."

The other was titled Two of Me.

"I have decided to share a little glimpse of the 'Creative Colin'," Craig said.

"There is only one of me it's true
"But I wish this were not the case
"Because I wish that I could have you
"If instead one man, I was two
"That would be one for all the others
"And one of me, for you."
Craig's relationship with the press was tragic and comical at times, MacGregor said.

MacGregor recalled a posed photo of Craig lying in a some long, thick grass during his 2014 election campaign.

"Oh dear," she muttered.

She said Craig had some issues during his interactions with the New Zealand media.

She tried several times to stop Craig from posing in the grass, but he insisted it was fine, she said.

"You can lead a horse to water but you certainly can't make it drink," she said.

She talked of Craig's "sleep trick" and shoulder massages for his "horrendous pain".

"[The sleep trick], he reckons it was him imagining himself lying on my legs," she said.

"[And] he would ask me to rub his shoulders - to help him perform in his interviews ... apparently. I don't actually know if that was the case.

"Now that I look back at it I wonder if he just wanted me to rub his shoulders?"

Colin Craig had the ability to make a normal media interview a disaster, Rachel MacGregor said. Photo / Dean Purcell
Colin Craig had the ability to make a normal media interview a disaster, Rachel MacGregor said. Photo / Dean Purcell

MacGregor also spoke of a TV interview at a shopping complex.

After being asked to interview Craig, MacGregor said she needed to prepare him for camera and went to find some make-up.

"When I came back he was already in front of the camera ... [the interviewer] was having some fun just asking him all sorts of ridiculous questions. By the time I got there it was too late."

She said Craig was discussing "a bunch of conspiracy theories", including chemtrails and questioning if man had landed on the moon.

Craig didn't see it as a problem until he watched it on the news, she said.

"He had the ability to make a normal media interview a disaster," she said.

A couple of days before election night 2014, Helen Craig says MacGregor rang her.

MacGregor, according to Helen Craig, admitted to having emotional affairs with the political leader.

MacGregor then quit as press secretary.

"As might have been expected, the resignation of a close adviser to the leader of a political party only two days before an election excited a great deal of news media interest," Justice Toogood would write.

"Public opinion polls conducted in the lead-up to the election suggested the Conservative Party was well supported, but it failed two days later to secure a sufficient number of the Party votes cast under the mixed member proportional voting system to reach the five per cent threshold which would have entitled it to seats in the House of Representatives."

Newstalk ZB's political editor Barry Soper was called to give evidence during the trial about a phone call he shared with MacGregor before news broke of her resignation.

Soper said he called MacGregor, whom he had previously worked with in television, just 48 hours before the general election.

"She was crying," Soper said.

Rachel MacGregor, centre, arriving at High Court to give evidence in Colin Craig's defamation case against Cameron Slater. Photo / Nick Reed
Rachel MacGregor, centre, arriving at High Court to give evidence in Colin Craig's defamation case against Cameron Slater. Photo / Nick Reed

The court was played three recordings from press interviews with Craig in the aftermath of MacGregor's resignation - where Craig claimed he was unaware why his press secretary had abruptly resigned.

Soper said the scandal, as rumours swirled of an affair between Craig and his press secretary, quickly became "the major story in the last 48 hours of an election campaign".

On the day she resigned, MacGregor filed a complaint with the Human Rights Commission, alleging Craig sexually harassed her.

The complaint was confidential and Craig only learned of its existence in late January 2015.

A confidential settlement between the two was reached in May 2015 - but details were later leaked.

In her testimony, MacGregor believed Craig had "set aside a million dollars and was going to destroy me" and talked of the mediation hearing.

"I remember two main things about the mediation," she said.

"One was that my lawyer was reading out lines of [Craig's] letters about how he wanted to kiss me, and Colin was adamantly saying that he treated me like a sister the whole time."

She said Craig was saying, "yeah, well, I'd kiss my sister. I'd do what I say in the letter to my sister".

Colin Craig's wife Helen says she received a phone call from Rachel MacGregor admitting to an emotional affair with her husband. Photo / Nick Reed
Colin Craig's wife Helen says she received a phone call from Rachel MacGregor admitting to an emotional affair with her husband. Photo / Nick Reed

MacGregor said the "mutual resolution", which Craig wanted it called, also implied she would withdraw her complaint of sexual misconduct to the Human Rights Commission.

"There is no way I have ever withdrawn my allegations, to this day my allegations stand concrete strong. What I withdrew was my complaint," she said.

The now public affairs manager said she ran out of energy to deal with a "very weird man" who was "deluded, weird and wrong".

"I wanted to just get on with my life and never have anything to do with him again."

In 2016, Craig was ordered to pay MacGregor more than $120,000 by the Human Rights Review Tribunal after it ruled he breached the agreement in media interviews.

As his dramatic fall was captured by the full glare of the constituents, Craig hit back.

He targeted what he called the trio of "schemers", whom he believed had plotted against him in a calculated and ruthless character assassination.

The three men were New Zealand Taxpayers' Union founder Jordan Williams and Conservative Party board member John Stringer, and Slater.

In response to allegations he sexually harassed MacGregor, Craig published a booklet called Dirty Politics and Hidden Agendas which he distributed to 1.6 million Kiwi households and held a press conference.

The pamphlets came at a personal cost of more than $250,000.

Included in it was an interview with Mr X, a foulmouthed whistleblower who said Craig was "freakish under pressure". However, it was later revealed Craig was in-fact Mr X and had fabricated the interview.

This booklet details the latest action by the "Dirty Politics Brigade", Craig said, adding: "What they have done is not legal and therefore court action is being taken against them."

A jury awarded Jordan Williams, centre, $1.27 million in damages after being defamed by Colin Craig. Photo / Nick Reed
A jury awarded Jordan Williams, centre, $1.27 million in damages after being defamed by Colin Craig. Photo / Nick Reed

Williams and Craig then went to court.

Craig was sued for defamation after what he said in the pamphlet and after a nearly four-week trial in 2016, a jury awarded Williams the full amount of his claim - $1.27 million.

It was the largest amount awarded in damages for defamation in New Zealand's legal history, which will now be re-examined by the Supreme Court on appeal.

It is estimated Craig spent $1m in legal fees in his case against Williams.

Craig and Stringer later reached an out-of-court settlement before the pair were set to go to trial in March last year.

Then, in May 2017, it was Slater's turn in court against Craig.

The pair came together and counter-sued each other, with Craig now representing himself.

He said the allegations written on Slater's blog site were irresponsible, inaccurate and very damaging.

Absent of a jury, Justice Toogood agreed and found Slater had defamed Craig in two untrue statements - repeated five times.

The judge ruled Slater defamed Craig by claiming he placed MacGregor under financial pressure to sleep with him and sexually harassed at least one other victim.

But Justice Toogood declined to award Craig damages.

"I have also held that the reputational damage which Mr Craig suffered throughout the events traversed at length in this judgment resulted almost entirely from his own actions.

"I conclude, therefore, that Mr Craig is not entitled to an award of general damages to compensate him further for such damage."

Blogger Cameron Slater counter-sued Craig for what was in the pamphlet and said at a press conference. Photo / Doug Sherring
Blogger Cameron Slater counter-sued Craig for what was in the pamphlet and said at a press conference. Photo / Doug Sherring

For Slater's counterclaim, Justice Toogood said while Craig's defence of truth failed he was protected by qualified privilege.

"Although Mr Craig countered the Whaleoil publications which he considered to have defamed him by asserting in the Dirty Politics and Hidden Agendas booklet that there was a conspiracy between Mr Slater, Mr Williams and Mr Stringer to spread deliberate lies about him, his primary motive was to correct what he had maintained throughout were untrue statements," the judge said.

"Because the core allegations about Mr Craig's relationship with Ms MacGregor and related matters had received widespread publication throughout New Zealand, I have found that Mr Craig's decision to distribute the booklet to every New Zealand household was a justifiable response."

Responding to Toogood's decision, Craig said he was "pleased but not surprised" by the result.

However, he also maintained he has never sexually harassed anyone.

"I was disappointed by a finding that I had done so on two occasions," he said.

Craig said his poems and letters were received with positive responses at the time.

"This is a perplexing outcome," Craig said.

"If someone tells you it's a great letter and they are re-reading and re-reading it, I think a normal person would consider the letter welcomed."

Despite claiming the win, Craig said he is now considering an appeal.

He was concerned the law was incorrectly applied and he should have succeeded on some claims against Slater which the judge dismissed.

Slater responded to the decision by writing a blog post following the decision quoting Justice Toogood's remarks about him.

"His honour Justice Toogood also made some very important comments about, how I handled the story and my own personal ethics in covering stories," Slater wrote.

After spending an estimated $1 million in legal fees for his case with Jordan Williams, Colin Craig has been representing himself in court. Photo / Michael Craig
After spending an estimated $1 million in legal fees for his case with Jordan Williams, Colin Craig has been representing himself in court. Photo / Michael Craig

MacGregor, meanwhile, who was cross-examined for two full days during the trial, was finally accepted as a victim.

In a statement, the Rachel MacGregor Trust - which helped fundraise for her legal fees - said Justice Toogood found Craig "overstepped any boundary which might have been appropriate for an employer in his communications to an employee".

"Mr Craig did not demonstrate, at any point in his evidence in this proceeding, any understanding of the difficulties created for an employee by an employer's expression of intense feelings of emotional engagement and sexual longing," the judge wrote.

"He never acknowledged the possibility that Ms MacGregor may have felt she could not protest about, and was obliged to tolerate, sexually charged language and conduct for fear of losing her employment or failing to meet her employer's expectations.'"

Despite this, MacGregor's legal proceedings with Craig may continue after the pair sued each other for defamation earlier this month.

Craig withdrew his claim for damages against MacGregor on day one of the trial after he became aware she could not pay him if he won the case.

We now wait for Justice Anne Hinton's decision on Craig and MacGregor's case.