One was his daughter Maryanne, who since 1997 had worked alongside her father as chief executive of the Hugh Green Group, which has interests in property, farming and construction.
The other was his eldest son John, who had long butted heads with his younger sister and after a 15-year absence had returned to the group in 2009. Determined to have a role in the family business, John pressured his father to remove Maryanne from Green Group trusts.
Hugh would die half a year later in July 2012, only months after penning his final will.
Maryanne would spend the next three years fighting to regain some control of a business that she had "lived and breathed".
And this month she won a major victory in the High Court at Auckland, which ruled that her father's final will was invalid.
That document, signed in April 2012, added two of Hugh's children - John and Frances Green - and lawyer Michael Fisher as executors.
This small change had a big impact and meant they could then appoint people to the trusts that control the entire Green Group.
In another victory for Maryanne, it was also found that when Hugh removed her from these trusts in December 2011, and later voted to expel her as a director of group companies, he was subject to undue influence from John.
This was not the only line of argument Maryanne had run. She also claimed her father lacked the necessary capacity when he signed his last will, removed her from positions of power and appointed her siblings and Fisher in them.
The defendants, which included Frances and John, said that while Hugh's decision to remove Maryanne was upsetting for him, he made it of his own free will and knew what he was doing.
They painted a picture of Hugh as a man in physical decline but still with the mental ability to navigate complex business issues.
Justice Helen Winkelmann, in her judgment, said Hugh's cognitive ability and capacity fluctuated.
He was prone to short-term memory lapses and, at times, found business matters that once were easy and enjoyable, stressful and confusing.
Maryanne Green worked alongside her father at the Hugh Green Group.
From November 2011, he was losing his energy, focus and decisiveness.
But Maryanne failed to prove to the judge that her father had lacked capacity when making the disputed decisions.
Justice Winkelmann also found that when Hugh appointed John and Frances to Green Group trusts and companies, he was exercising his own free will.
This was not the case, however, when it came to removing Maryanne as a trustee six weeks later.
"Every act taken around the removal of Maryanne seems to have been instigated by someone other than Hugh ... I am satisfied that John's determination to have a role in the Green Group, and to free himself of Maryanne's continued opposition and criticism, caused him to pressure his father to remove Maryanne," Justice Winkelmann said. "He set the stage for Maryanne's removal in every sense, and his conduct over-bore his father's will."
It was a similar state of affairs when Hugh voted to remove Maryanne as a director of Green Group companies and appoint Fisher to them.
"The influence that John was exercising over his father, with the unknowing assistance of Mr Fisher, hopelessly infected this decision. John had decided Maryanne had to go, and go from everything," the judge said.
The tensions between Maryanne and John were partly due to their different personalities.
There was evidence in the case that Maryanne was an "unusual person" and could be completely "without guile" in how she recounted events.
"My impression is that she is compulsively truthful, to the extent that she is prepared to strain family relations to the point of breaking them, in pursuit of the truth," Justice Winkelmann said.
But it was in more than just personality in which the siblings clashed.
Tensions between Maryanne and John also stemmed from his departure and resignation as a trustee in 1994. He left following an investigation into cattle trading when he was working at Kilmacrennan Livestock, the entity through which Hugh conducted his cattle trading business.
Justice Winkelmann said the evidence established that in the early 1990s John was involved in dishonest transactions and that he had frequently used Kilmacrennan funds in an unauthorised way, and on occasion kept them for his own purposes. While John continues to deny wrongdoing, the judge said she rejected his explanations "as not worthy of belief".
Despite any past behaviour, it is John's present hostility to Maryanne that could see him removed from Green Group's trusts.
Justice Winkelmann said the grounds were made out for the removal of both John and Frances as trustees because the "level of hostility" they feel and exhibit towards Maryanne and her daughter was enough to undermine the execution of the trusts.
With an appeal in the pipeline, a family reconciliation would appear as remote as ever.
Hugh Green
• Immigrated to New Zealand from Ireland in 1951. • Accumulated a fortune worth hundreds of millions of dollars during his long and successful business career. • Was known for his generosity and founded the Hugh Green Foundation, a charitable organisation that supports causes such as medical research or individuals living with disabilities or serious illness. • Was awarded a Queen's Service Medal for services to philanthropy six months before he passed away. • Died in July 2012 at 80.
