Colin Craig and his former press secretary settled their pay dispute and her sexual harassment claim with a confidential agreement in May 2015.
The deal meant the pair could only say they had met and "resolved their differences".
Within weeks Mr Craig began breaching the deal multiple times during what the Human Rights Tribunal described as "an intense period".
Mr Craig’s breaches started in early June 2015 during the now infamous sauna interview with TV3’s David Farrier, when he was asked whether he’d had an affair with Ms MacGregor.
He resigned the Conservative Party leadership ten days later, breaking the agreement again when he told media the suggestion he’d paid Ms MacGregor off over a complaint of sexual harassment was scurrilous and false.
More breaches followed three days later on June 22 when Craig held a media conference that he said was to address "wild speculations and allegations" about his dealings with Ms MacGregor.
Ms McGregor was blindsided by that media conference, finding about it only when work colleagues told her it was being live streamed.
Mr Craig told the media he and his wife Helen had been helping Ms MacGregor "bring her finances in order" and had extended an interest-free loan to her "to enable her credit card debt to be cleared".
He added: "Ms MacGregor however went into default on the payment of this loan and was unable to make payment. Subsequently she requested that the loan be forgiven on compassionate grounds."
However, Mr Craig failed to mention that the loan was interest free only for six months, after which he charged 4 percent. When Ms MacGregor filed her sexual harassment claim, the interest rocketed up to 29 percent.
The $18,990 loan was wiped as part of the sexual harassment and pay complaint that Ms MacGregor filed with the Human Rights Commission after quitting.
She had not been paid regularly in the four months leading up to her resignation as his press secretary because the pair disagreed over her contract rates.
The complaints were resolved in tandem, with Craig agreeing to "forgive" the loan and pay $16,000 to Ms MacGregor to settle both matters. As part of the confidential settlement she agreed to drop her sexual harassment complaint.
At the same media conference Craig said his working relationship with his former press secretary had been "positive and constructive".
"In hindsight, on some occasions our conduct was inappropriate and we have acknowledged that so we can both move on," he said. Ms MacGregor had not agreed to this statement.
Mr Craig went on to breach the confidentiality yet again when he sent a newsletter to 8,000 people on the Conservative Party mailing list. In it he said the sexual harassment allegations were wrong and had been withdrawn.
The following month, Mr Craig called another press conference, this time with his wife Helen to launch a booklet he said was aimed at combatting so-called dirty politics.
In the booklet, the former Conservative Party leader again said the sexual harassment claim was false. That breach of confidentiality went far and wide, with at least 1.2 million copies sent around the country.
Colin Craig has always denied any claim of sexual harassment and the allegations were outside the scope of the Human Rights Tribunal’s ruling.
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