The man who the late Princess Diana was alleged to have nicknamed ‘captain’ – while he affectionately referred to her as ‘boss’ – saw his life move from the back pages of newspapers to the front thanks to his very colourful love life.
In 1994, Will Carling, then 29, had won three major Grand Slams as captain of the England men’s rugby team, a position that meant his path would frequently cross with the royals, including Diana.
Somewhere between the hallowed turf at Twickenham and the fancy Chelsea gym the royal, then 33, and the rugby player shared, a friendship blossomed that would see Carling’s previously clean-cut image begin to flounder.
At the time, the rugged former public school boy was married to glamorous blonde television presenter Julia Smith, then 30, with the couple having wed in the same year.
Photos of Diana and Carling emerging from Chelsea Harbour Club separately were snapped – and the pair were said to have grown close after the witty princess told the professional sportsman that he was doing sit-ups incorrectly.
Post-workout refreshments in the club’s cafe followed, sparking a chain of events that would catapult Carling’s penchant for beautiful blonde women into the spotlight, and see him dubbed the ‘bad boy of English rugby’.
When it was disclosed to Julia that her husband was also visiting the Princess at Kensington Palace, his tell-tale blue Range Rover spotted in the car park, she publicly fired a warning shot at her royal rival, declaring that she had ‘picked the wrong couple’.
However, according to Tina Brown’s book The Palace Papers, Diana and Carling were close enough for him to be introduced to her sons.
Princess Diana and Will Carling in Cardiff, Wales, in 1995
The rugged former public school boy was married to glamorous blonde television presenter Julia Smith, then 30, with the couple having wed in 1994
‘William hero-worshiped Carling and met him several times with Diana,’ she said. ‘When Carling visited Kensington Palace for a romantic rendezvous, he gave both the boys a rugby shirt.’
While a romance was never confirmed and indeed were frequently dismissed by Kensington Palace as ‘pure speculation’, by September 1995, Carling had announced that he and Julia were set to divorce – and papers were inked the following year.
When reports of the divorce broke, Julia seemingly made it clear who she blamed for the destruction of the couple’s happy ever after, in a quote relayed to a newspaper by a friend, saying: ‘It would be easy to say she’s ruined my marriage, but it takes two to tango and I blame Will for getting involved in the first place.’
However, Julia herself later told another reporter: ‘This has happened [to Diana] before… you hope she won’t do these things again, but obviously she does.’
During a lunch in 1996 with Piers Morgan, at which a 13-year-old Prince Wililam was present, Diana made her feelings clear.
‘She’s milking it for all she’s worth that woman,’ she said. ‘I haven’t seen Will since June ’95.’
William added: ‘I keep a photo of Julia Carling on my dartboard at Eton.’
Meanwhile, Will hadretreated to a rented flat in Covent Garden, which wasn’t in his name, didn’t have a phone and was accessed via an underground car park.
Will Carling, Ali Cockayne and son Henryat the Cartier International Polo in Windsor in 1998
‘My parents didn’t even know where I lived,’ he said.’I lived there for a year and I never opened the curtains or blinds in case anyone looked in.’
A decade later in 2004, Carling was still adamant no affair had taken place with the late ‘Queen of People’s Hearts’, telling the Sunday Mirror: ‘No, no, no – how many times do I have to say it? We were friends…’
Of the end of his marriage with Julia, he said:’I have to admit that I didn’t handle things very well, not very well at all. But there are two sides to every story, and no one has heard mine. That’s my choice, and I live with it.’
However, just four years ago the ex England rugby star, who will celebrate his 60th birthday in December, was more candid about his bond with Diana, admitting he had been‘stupidly doing things you shouldn’t do’.
Speaking on a podcast, he confessed the whole period had been ‘a bit of a mess.’
Asked to explain, the sportsman said: ‘Just making messes of relationships because you’re sort of rudderless and you’ve lost your focus and you don’t behave well, and I didn’t.
‘Never intentionally or vindictively, I just think that was me, I just was in a bit of a mess.
You’re sort of like a car that’s lost a steering wheel and you’re careering all over the place. It wasn’t very pleasant; it was a fairly traumatic time.’
Will Carling and Lisaattend the Cartier International Polo at Windsor Great Park in 2006
His impending divorce from Julia might have abated interest in his personal life, had a new woman not breezed into the picture months before his marriage was officially over.
Ali Cockayne, then in her early thirties, knew the sporting world well; her sister Michelle was married to footballer-turned-BBC presenter Gary Lineker at the time.
When Ali and Carling were introduced at a testimonial dinner, their love affair quickly became serious and they went on to have a son,Henry, in 1997.
However, when Henry was just 11 months old, Carling appeared to swerve serious commitment once again, exiting the relationship in the midst of planning for their upcoming wedding.
Ali learned the rugby player had a new squeeze when she discovered a press release in the study of their luxury home in Sunningdale, Berkshire, which read: ‘Will Carling is leaving his partner Ali Cockayne for a future with Lisa Cooke.’
Lisa was the estranged wife of his friend and ex-England rugby player David Cooke, and their romance ignited again over another testimonial match, this time Carling’s own, at Wembley.
In the days after the break-up was revealed, Ali was seen clutching Henry to her chest, crying uncontrollably.
In 2024, Ali experienced the devastating death of her sonJonty, who she shared with hernew partner, Bob Parkinson.
Announcing he was leaving Ali in 1998, Carling (pictured in 1995) released a statement at the time through his agent, saying: ‘This has been a very sad and painful time for everyone concerned’
Carling, Aliand their son Henry, enjoying a day out at the Alfred Dunhill Queen’s Cup Polo at Smith’s Lawn, Windsor Great Park
Ali’s agony was captured poignantly at the time of her split with Carling in a photograph, showing her clutching their son Henry to her chest, and crying uncontrollably
The 18-year-olddied of a crush injury to his abdomen after a tree accident in Oxfordshire.
Announcing he was leaving Ali in 1998, Carling released a statement at the time through his agent, saying: ‘This has been a very sad and painful time for everyone concerned.
‘It is even more difficult and emotional because of Henry, but I plan to fulfil my duties and responsibilities as a father.’
The couple’s dramatic split happened just a month after Will retired from rugby.
After his new love affair with Lisa became public, the rugby player was reportedly fined £1 million for cancelling a test match due to the fall-out.
A year later, Carling and Lisa married in Fiji in 1999 with her two children, Tom and Tali, from her earlier marriage the only guests. They went on to have two children, Jack and Mimi, together.
Carling later said that it was Lisa who ‘transformed his life’ and that family ‘is just it for me’.
The ex-army officer, whose rugby career spanned nine years, previously opened up about undergoing therapy with John Cleese’s ex-wife, Alyce Faye Eichelberger.
He reflected later that he hadn’t always behaved the way he should have done, saying: ‘As a sportsman you lead a very selfish life.
Lisa (pictured right) was the estranged wife of his friend and ex-England rugby player David Cooke, and their romance ignited again over another testimonial match, this time Carling’s own, at Wembley
Carlinglooks on during the England training session held at Twickenham Stadium on February 14, 2020 in London
‘But now, for the first time, I’m willing to concede that I’m not always right and not to think that things should always be my way.’
He added: ‘I’d hate to think I’d ever get complacent or boast that ours was the best relationship anyone’s ever had. I think you have to work hard to stay happy, which for me means always talking instead of bottling up your feelings as I used to do.’
Last year, he reflected in The Telegraph in 2024 on how being linked to one of the most famous women in the world, Princess Diana, was a ‘good story’.
He said: ‘Front page is very different from back page. Yeah, it was not nice.
‘Hey, a lot of that is my own fault, you can’t complain. You have to learn. Relationships that I got wrong…so, that’s what they got fascinated by. You look back on it and you think it was all blown out of all proportion, but it made a good story.’
Now, Carling lives a much more low-key life, concentrating on being the best dad and family man he can be.
He told The Royale in 2015 of his new hobbies: ‘I’m obsessed with [cycling] and clock up about 250km a week. I analyse all kinds of stats and love talking about kit.
‘I’m 49 and I’ve become a Middle-Aged Man In Lycra – it’s sad, but I can’t help it,’ added the sportsman.
He has worked as a TV pundit, a motivational speaker and in the hospitality industry, while also acting asleadership mentor toEddie Jones’ England rugby team.
