The spotlight is now on WiseTech’s directors.

Until the board received questions about White’s conduct and relationships, many of the directors who joined after 2020 were unaware of many of the issues. But two directors, Isaacs and Charles Gibbon, a key figure at Shearwater Capital, once a big investor in the company, have served on the board for more than a decade.

For years, White crafted an image of a humble tech nerd who championed female entrepreneurs. Several of these women have alleged inappropriate behaviour by the billionaire, who had contacted them via LinkedIn or at business functions. White traded on what one described as his “wealth, fame and business status” in his offers to help. But it soon became clear White’s interests were of a sexual nature, the women said.

Meanwhile, White’s chaotic private life had resulted in confidential settlements, legal actions and an allegation of inappropriate behaviour by a former lover, which reached the board. In March 2021, White finalised a confidential settlement and paid a former lover several million dollars while still denying the allegations. Of the current directors, only Gibbon and Isaacs were on the board at the time.

Gibbon hung up when called, declining to comment. Isaacs did not respond. Gibbon, and his investment vehicles, also own 5.5 per cent of WiseTech and has been a shareholder since 2005.

The pair did not answer questions about why they did not tell new directors about allegations made against White in 2020 which resulted in the businessman paying a woman he was in a relationship multiple millions, the level of disclosure about his relationship with an employee, his alleged conduct towards another director – and whether they intend to stay on the board.

Mystery legal action

Given Richard White’s extraordinary wealth – and his use of it to solve other crises – it is a mystery why he decided to pursue Sydney wellness entrepreneur Linda Rogan over just $92,000. Rogan had been in a relationship with White, she told the Federal Court, and purchased furniture to fill a Vaucluse mansion he bought for her.

When the relationship fell apart, after its discovery by White’s now-wife Zena Nasser, the businessman began to pursue her for repayment of the furniture bill. The publicity cascaded into the crisis that ultimately led to White stepping down from WiseTech on Thursday.

It had been a long time coming. It was early last year that Rogan first started her own legal action against White for the $92,000 she had spent. White ignored the matter and Rogan was allowed by the court to take the money from his account. A few months later, White had the judgment overturned and began demanding Rogan repay him.

When she didn’t, he set about bankrupting her. Rogan retaliated with an explosive 143-page affidavit, alleging White was pursuing her not for the money but because they had once been in a relationship. He had offered to help her with her business too, she alleged, an offer which became tied to sex after a trip to New York. White and Rogan settled this week.

Two months before launching his legal action against Rogan, White appeared on the Financial Review’s podcast. Explaining the key to his success and his wealth, White said he spent time “ensuring there are no risks or I’ve got plans when the risks happen”. This aptitude appears to have failed White on this occasion. So what went wrong?

A month after the podcast, White marked two significant life events. White, 69, and Zena Nasser, 45, tied the knot in Austin, Texas while celebrating the birth of their daughter born via an American surrogate.

Nasser had approached White via LinkedIn in early 2020 when Sydney was in the midst of COVID-19 lockdowns. The relationship blossomed in June when restrictions were lifted – even though White was living with Christine Kontos, a logistics expert employed by WiseTech and for whom the businessman bought a $7 million house in Melbourne.

White’s 2015 divorce from his first wife Barbara had been acrimonious, and the following year he began a relationship with Kontos. But while White was living in his Bexley compound with Kontos, he was also in a long-term sexual relationship with another woman.

In February 2020 that woman placed a caveat on a Lane Cove house, claiming she and White had made an oral agreement the $4.8 million house he purchased was to be hers. Later that year, the woman made explosive allegations against White, including about his alleged misuse of corporate funds, which threatened to derail his career.

Nasser helped craft the deed the woman signed in March 2021. But on that same day, Sutherland Local Court heard Nasser was applying for an AVO against White. It was withdrawn several months later via a sworn affadavit.

Nasser, 45, had been a criminal lawyer who was once held at gunpoint by masked men during a home invasion. She had an array of Sydney underworld figures as clients, from bikie boss Hassan Kalache and drug importer Michael Ibrahim to gang leader Bassam Hamzy.

In July 2007, Nasser was banned from visiting jails in NSW because Corrective Services had reason to believe that she was forwarding her clients’ calls to their associates on the outside. She was deemed a security risk.

Nasser had represented Michael Ibrahim, the brother of nightclub boss John Ibrahim, who was jailed in April 2008 for manslaughter. But when Michael’s brother, Fadi, didn’t foot her firm’s $150,000 legal bills as promised, Nasser lodged a caveat on the Castle Cove home outside of which Fadi was later shot five times as he sat in his Lamborghini.

Relations with the Ibrahim family were repaired as corporate records indicate that Nasser was later a director and shareholder of Krazye Dave Pty Ltd, a company associated with one-time bikie enforcer Sofe Veiru Levi, better known as “Crazy Dave” Lima.

Lima, who has a conviction for violence, is a close associate of the recently convicted tax fraudster and money launderer George Alex. “Crazy Dave” was also second-in-charge of the bikie gang known as Notorious. Both Sam and Michael Ibrahim were involved in the gang.

When Nasser’s caveat on Fadi Ibrahim’s house was finally lifted in March 2010, her signature was witnessed by her then-husband, developer Mark Merhi, with whom she has a daughter.

By 2020, when Nasser had struck up a relationship with White, things were fraying for Merhi. His Aya Eliza developments in Sydney’s west – which he dubbed “architectural landmarks of the finest standard” – were described as an “abomination” by government authorities. His company subsequently collapsed, and he fled the country in 2022 with corporate debts of $80 million.

It was around this time Nasser was introducing Rogan to White. Rogan described herself on Instagram as a “beauty addict” and owned a laser clinic in Sydney’s Double Bay. Rogan was “sooo hot” Nasser just had to “message this stunning lady x”. In August, Nasser organised for Rogan to join her and White for dinner at Bambini Trust, an institutional Sydney restaurant popular with lawyers and businesspeople, after which the trio went to White’s penthouse in the nearby Eliza apartment block overlooking Hyde Park.

In corporate documents, Nasser lists her address in that upmarket complex where White has spent more than $32 million acquiring five of 19 apartments. Her four-bedroom apartment, which occupies the entire eighth floor, was bought by White for $6.5 million.

He had also purchased the Eliza penthouse for $15.5 million via a company fronted by two of White’s friends, his “gopher” Reg Kennedy, and Tony Jex, the former drummer from a little-known 1970s band Jade in which White was the guitarist.

And he had recently outlaid $27.5 million for a trophy home in fashionable Palm Beach.

“I want to make you and your business massively successful,” White wrote to Rogan, once a contender to appear in The Real Housewives of Sydney, in August 2022.

That year proved to be a calamitous one for White’s private life. At the beginning of October, Nasser had forced White to end his relationship with his long-term partner Christine Kontos.

By month’s end, Nasser discovered White’s relationship with Rogan. “You didn’t have to lie … Richard admitted it … don’t come near me again,” she said in a text to Rogan.

Apart from the affair, Nasser also discovered White had used another front company, Maravillosa, to allegedly hide his purchase of a $13.1 million home in Vaucluse for Rogan. In her affidavit, Rogan said White explained the deal was structured to ensure “that no one can trace the property back to me or you. Zena will never know I own this house”.

But White’s clandestine scheme misfired and, after seizing control of Maravillosa, Nasser evicted Rogan – who’d only possessed the love nest for three weeks. While Nasser was dealing with her rival, White was nowhere to be seen.

Except at the office. Why White clung on to his job at the top of WiseTech as his personal life disintegrated, and despite a $11 billion fortune, is a question only he can answer.

It is a question that the businessman went some way to answering when, as the cake was cut on Thursday afternoon in the company’s Alexandria office, White told his staff that he had been struck by the reality that he was simply holding to the job. “I’ve been the happiest I’ve been in so long,” he said.

Echoing Tom Wolfe’s The Bonfire of the Vanities, which chronicles the downfall of a Wall Street banker, White’s life unravelled spectacularly. Despite their vast discrepancies in wealth, White ruthlessly pursued his former lover Rogan for the relatively paltry bill for their unused outdoor love seats and the bed they never slept in. Hubris was his downfall.