Why Rupert Murdoch really called off his fifth engagement

Rupert Murdoch met Ann Lesley Smith, inset, at his Bel Air vineyard last year. Photos / AP, Facebook

Ann Lesley Smith has a motto: “Where your problems are, there is a pearl.” But when it comes to the problems with her recent engagement to Rupert Murdoch, it seems there was not so much a pearl as a major, insurmountable rock. And it wasn’t the one he proposed with, an 11-carat diamond worth about £2 million (NZ$3.9m).

Just two weeks after the 92-year-old media mogul announced his forthcoming fifth marriage in the pages of one of his own titles, The New York Post, the match has been called off. As news spread around the world that the relationship had floundered months before the wedding, outsiders asked, in surprise, how on earth it had all gone wrong at such dizzying speed.

“We’re both looking forward to spending the second half of our lives together,” Murdoch had said of his latest and, he promised, his last fiancée.

Murdoch met Smith at his Bel Air vineyard six months earlier and had just finalised his divorce from Jerry Hall, 66. A source tellingly says “he can’t just be on his own”.

Hall was popular with his friends and family – she’s used to the spotlight and friends say she was “perfect for him – she is jolly and kept his spirits up”. She was a hard act to follow, especially for Smith, who has staunch political opinions. Were 66-year-old Smith’s views too extreme even for the owner of Fox News in the end? A source close to the Australian businessman said he had become “increasingly uncomfortable with Smith’s outspoken evangelical views”.

Rupert Murdoch and Jerry Hall at the 2019 Vanity Fair Oscar Party. Photo / Getty Images

Another US-based source says: “Apparently the right-wing evangelical stuff was too much even for him. And I know the kids have been worried from the start because she’s likely to come out with some pretty bonkers stuff to anyone who asks.”

On her radio show previously, the Californian divorcee and former San Francisco police chaplain had appeared to express Covid denial, telling listeners: “They try to close down people’s business. Do they know what this is doing? It’s part of the plan, the Plandemic – oops! – pipeline. It comes and it swoops over. It’s invented for the most part, it’s killing a lot of people.”

It has also been suggested that Smith struggled with the overwhelming media attention that her relationship with Murdoch brought her. A friend close to the couple has been reported saying she “just could not cope with being in the public eye”, and that after sitting down and talking, the pair agreed it was best to go their separate ways.

But there may have been something else going on behind the scenes as well. According to David Folkenflik, Murdoch’s biographer, it appears “poor vetting by the Murdoch camp” is to blame for the rapid reverse ferret – as the U-turn might have been called at Murdoch’s British tabloid The Sun during the 1980s. Not only “poor vetting” of her world view, but perhaps more importantly of her backstory.

As another source says, “she seems to come with a bit of history of her own”, and it’s a history that comprises three previous marriages. The first was to John B. Huntington, who came from one of California’s pioneering railroad families. It reportedly ended in a bitter divorce, which Smith has claimed left her with nowhere to live and relying on welfare payments. “I was ashamed,” she once told an interviewer. “I really wanted to commit suicide ‘cause my life was just so bad.”

She found her faith when, during a modelling job in that period, an event coordinator handed her a book, The Four Spiritual Laws.

Rupert Murdoch's engagement to Ann Lesley Smith, a 66-year-old former dental hygienist whom he met at his vineyard in Los Angeles, is said to have been called off after two weeks. It would have been his fifth marriage. https://t.co/eO3ccv8Gs3

— The New York Times (@nytimes) April 5, 2023

In 1999, she reportedly married Michael Carabello, a former member of the band Santana. The marriage is said to have lasted about a year. The Telegraph has approached a representative of Carabello for comment.

She then married the country singer Chester Smith, and appears to have enjoyed a happy if brief union with him until his death about three years later, in 2008, at the age of 78.

The aftermath of this marriage is what appears to have sparked consternation in the Murdoch camp, Folkenflik suggests.

According to media reports, one of Smith’s daughters, Roxanne Storey, sued Ann Lesley Smith in 2008, alleging that as trustee of his estate, her stepmother had failed to give her and her two sisters their fair share of the inheritance.

Judge Duane Martin ruled that “the court has lost all confidence in [Ann Lesley Smith’s] ability to administer the trust other than for her own benefit, in conflict with her fiduciary duty to Chester Smith’s three daughters”. The case was settled out of court.

“Somebody with that kind of record would be someone you’d want to keep away from Murdoch’s estate,” says Folkenflik, author of Murdoch’s World (2013).

Although Murdoch’s lawyers would likely have had “a pretty iron-clad prenup in place”, someone who appears to have been involved in legal wrangling over the estate of a previous husband may have rung alarm bells. “[These are] exactly the complications the Murdoch children don’t want any part of, and that Rupert doesn’t want any part of,” says Folkenflik.

Murdoch’s third marriage, to Wendi Deng, from 1999 to 2014, was, he says, “incredibly threatening to the adult [Murdoch] children” – partly because, being almost four decades younger than him, Deng was going to outlive him by a long stretch; and partly because the marriage generated two more children, Grace and Chloe.

“He’s always generous after a split,” says one source. “So [his children] would be urging caution.”

‘There will be another one’

Despite calling off his fifth marriage, a source who says Murdoch doesn’t like being single suspects “there will be another one very soon”.

It takes a certain type of person to fulfil the brief: gets on with his family, understands the glare of publicity that comes with marrying the world’s most famous press baron, is sensitive to the needs of a man in his later years – but equally has the required glamour. A mix of astute Wendi, glitzy Jerry and the supportive Anna… if there were a real-life Harriet Walter from Succession, that would fit the bill.

There is likely to be no shortage of candidates, says Folkenflik. “God knows if Murdoch wanted companionship there’s probably any number of women willing to step forward and provide that kind of company. But it would seem that [Smith was] a pretty problematic choice.”

As for the ring, it remains in doubt whether Smith will get to keep it.

“I guess after such a short stint she’ll have to hand it back,” says a source.

It may, after all, be needed for the next Mrs Murdoch.

- Additional reporting by Faye Mayern